Alkyl 2-methyl-3-phenyloxirane-2-carboxylate [Reaxys, Substances Details (30); 2016-02-16]

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30 substances in Reaxys

2016-02-16 06h:57m:04s (EST)

ALK O O

1. Query O

Search as: As drawn

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Reaxys ID 181277 View in Reaxys

O

1/30 CAS Registry Number: 41232-97-7 Chemical Name: ethyl ester of the 2-methyl-3-phenyl-2,3-epoxypropionic acid; 2-methyl-3-phenyl-oxiranecarboxylic acid ethyl ester; 2.3-Epoxy-2-methyl-3-phenyl-propionsaeure-aethylester; 3-Phenyl-2-methyl-2,3-epoxy-propionsaeure-aethylester; Aethyl-α-methyl-β-phenylglycidat; 2-Methyl-3-phenyl-glycidsaeureaethylester Linear Structure Formula: C12H14O3 Molecular Formula: C12H14O3 Molecular Weight: 206.241 Type of Substance: heterocyclic InChI Key: PTJLNEHAZVPEFQ-UHFFFAOYSA-N Note:

O

O

Substance Label (6) Label References epoxide 1f

Chakraborty, Tushar K.; Ghosh, Animesh; Raju, T. Venugopal; Chemistry Letters; vol. 32; nb. 1; (2003); p.

82 - 83, View in Reaxys

VIII

Kuroyan, R. A.; Markosyan, A. I.; Engoyan, A. P.; Vartanyan, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 19; (1983); p. 1709 - 1714; Zhurnal Organicheskoi Khimii; vol. 19; nb. 9; (1983); p.

1947 - 1953, View in Reaxys

I

Bokanov, A. I.; Persianova, I. P.; Shvedov, V. I.; Journal of Organic Chemistry USSR (English Translation); (1982); p. 971 - 972; Zhurnal Organicheskoi Khimii; vol. 18; nb. 5; (1982); p. 1122 - 1123, View in Reaxys

2-Methyl-3-phenylglycidat 1

Kagan; Przybytek; Firth; Singh; Tetrahedron Letters; vol. 13; nb. 50; (1972); p. 5133 - 5136, View in Reaxys

Ic

Singh; Kagan; Journal of the American Chemical Society; vol. 91; (1969); p. 6198, View in Reaxys

20

Patent; Union Carbide Corp.; US3141027; (1959); GB863446; Chem.Abstr.; nb. 25982; (1961), View in Reaxys

Related Structure (1) References Walborsky,H.M.; Colombini,C.; Journal of Organic Chemistry; vol. 27; (1962); p. 2387 - 2390, View in Reaxys Boiling Point (3) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

110

2

Kuroyan, R. A.; Markosyan, A. I.; Engoyan, A. P.; Vartanyan, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 19; (1983); p. 1709 - 1714; Zhurnal Organicheskoi Khimii; vol. 19; nb. 9; (1983); p. 1947 - 1953, View in Reaxys

128 - 130

5

Martynow; Below; J. Gen. Chem. USSR (Engl. Transl.); vol. 32; (1962); p. 2341,2308, View in Reaxys

121

4

Patent; Union Carbide Corp.; US3141027; (1959); GB863446; Chem.Abstr.; nb. 25982; (1961), View in Reaxys

Refractive Index (3) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Re- References fractive Index) [°C]

1.509

589

20

Kuroyan, R. A.; Markosyan, A. I.; Engoyan, A. P.; Vartanyan, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 19; (1983); p. 1709 - 1714; Zhurnal Organicheskoi Khimii; vol. 19; nb. 9; (1983); p. 1947 - 1953, View in Reaxys

1.5082

589

20

Martynow; Below; J. Gen. Chem. USSR (Engl. Transl.); vol. 32; (1962); p. 2341,2308, View in Reaxys

1.5052

589

30

Patent; Union Carbide Corp.; US3141027; (1959); GB863446; Chem.Abstr.; nb. 25982; (1961), View in Reaxys

Density (2) 1 of 2

Density [g·cm-3]

1.117

Reference Temperature [°C]

4

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Measurement Tempera- 20 ture [°C] Kuroyan, R. A.; Markosyan, A. I.; Engoyan, A. P.; Vartanyan, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 19; (1983); p. 1709 - 1714; Zhurnal Organicheskoi Khimii; vol. 19; nb. 9; (1983); p. 1947 - 1953, View in Reaxys 2 of 2

Density [g·cm-3]

1.0865

Reference Temperature [°C]

4

Measurement Tempera- 20 ture [°C] Patent; Union Carbide Corp.; US3141027; (1959); GB863446; Chem.Abstr.; nb. 25982; (1961), View in Reaxys Crystal Property Description (1) Colour & Other Location Properties orange

supporting information

References Concellon, Jose M.; Bernad, Pablo L.; Rodriguez-Solla, Humberto; Diaz, Pamela; Advanced Synthesis and Catalysis; vol. 351; nb. 13; (2009); p. 2178 - 2184, View in Reaxys

Further Information (1) Description (Fur- References ther Information) Further information

Valente; Wolfhagen; Journal of Organic Chemistry; vol. 31; (1966); p. 2509,2510,2511, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Concellon, Jose M.; Bernad, Pablo L.; Rodriguez-Solla, Humberto; Diaz, Pamela; Advanced Synthesis and Catalysis; vol. 351; nb. 13; (2009); p. 2178 - 2184, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

75

Location

supporting information

Concellon, Jose M.; Bernad, Pablo L.; Rodriguez-Solla, Humberto; Diaz, Pamela; Advanced Synthesis and Catalysis; vol. 351; nb. 13; (2009); p. 2178 - 2184, View in Reaxys 3 of 3

Description (NMR Spec- NMR troscopy) Valente; Wolfhagen; Journal of Organic Chemistry; vol. 31; (1966); p. 2509,2510,2511, View in Reaxys; Kagan et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 2355,2361, View in Reaxys

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

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Comment (IR Spectroscopy)

neat liquid

Concellon, Jose M.; Bernad, Pablo L.; Rodriguez-Solla, Humberto; Diaz, Pamela; Advanced Synthesis and Catalysis; vol. 351; nb. 13; (2009); p. 2178 - 2184, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

HRMS (High reso- supporting inforlution mass spec- mation trometry); Spectrum

Concellon, Jose M.; Bernad, Pablo L.; Rodriguez-Solla, Humberto; Diaz, Pamela; Advanced Synthesis and Catalysis; vol. 351; nb. 13; (2009); p. 2178 - 2184, View in Reaxys

Reaxys ID 158406 View in Reaxys

O

2/30 CAS Registry Number: 80532-66-7 Chemical Name: methyl-2-methyl-3-phenylglycidate; 2-methyl-3-phenyl-oxiranecarboxylic acid methyl ester; 2,3-epoxy-2methyl-3-phenyl-propionic acid methyl ester; 2,3-Epoxy-2-methyl-3-phenyl-propionsaeure-methylester Linear Structure Formula: C11H12O3 Molecular Formula: C11H12O3 Molecular Weight: 192.214 Type of Substance: heterocyclic InChI Key: CPPPKJUXIISPJL-UHFFFAOYSA-N Note:

O

O

Substance Label (4) Label References 8b

Zimbron, Jeremy Malcolm; Seeger-Weibel, Manuela; Hirt, Hans; Gallou, Fabrice; Synthesis; nb. 8; (2008); p. 1221 - 1226, View in Reaxys

32a methyl ester

Satoh; Kitoh; Onda; Takano; Yamakawa; Tetrahedron; vol. 50; nb. 17; (1994); p. 4957 - 4972, View in Reaxys

16

Heathcock,C.H.; Pirrung,M.C.; Young,S.D.; Journal of the American Chemical Society; vol. 106; (1984); p.

8161, View in Reaxys

Epoxyester 10; R = Me; R1 = Me

Roux-Schmitt et al.; Tetrahedron; vol. 28; (1972); p. 4965,4968, 4975, View in Reaxys

Related Structure (2) Related Structure References hlor-propionPatent; Knoll A.G.; DE702007; (1938); DRP/DRBP Org.Chem., View in Reaxys saeure-methylester, Natriumaethylat und Aethanol erhalten worden.

Ein Praeparat Beilstein Handbook, View in Reaxys (Kp&11%: 136-140grad), in dem wahrscheinlich ueberwiegend (2#RS!, 3#SR!)-2,3-Epoxy-2-methyl-3phenyl-propionsaeure-methylester (C11H12O3, Formel X <X=OCH3>+Spiegelbild) vorgelegen hat, ist beim Behandeln von Ben-

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zaldehyd mit (+-)-2-C. Boiling Point (3) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

73 - 74

0.2

Gladiani, S.; Soccolili, F.; Synthetic Communications; vol. 12; nb. 5; (1982); p. 355 - 360, View in Reaxys

85

0.1

Roux-Schmitt et al.; Tetrahedron; vol. 28; (1972); p. 4965,4968, 4975, View in Reaxys

136 - 140

11

Patent; Knoll A. G.; DE702007; (1938); DRP/DRBP Org.Chem., View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Satoh; Kitoh; Onda; Takano; Yamakawa; Tetrahedron; vol. 50; nb. 17; (1994); p. 4957 - 4972, View in Reaxys 2 of 2

Description (NMR Spec- NMR troscopy) Roux-Schmitt et al.; Tetrahedron; vol. 28; (1972); p. 4965,4968, 4975, View in Reaxys

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

1745 cm**(-1)

Satoh; Kitoh; Onda; Takano; Yamakawa; Tetrahedron; vol. 50; nb. 17; (1994); p. 4957 - 4972, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) electron impact (EI); spectrum

Satoh; Kitoh; Onda; Takano; Yamakawa; Tetrahedron; vol. 50; nb. 17; (1994); p. 4957 - 4972, View in Reaxys

Reaxys ID 13545 View in Reaxys

O

3/30 CAS Registry Number: 7042-28-6; 7141-24-4; 41232-97-7 Chemical Name: (2RS,3SR)-2,3-epoxy-2-methyl-3-phenyl-propionic acid ethyl ester; (2RS,3SR)-2,3-Epoxy-2-methyl-3-phenylpropionsaeure-aethylester; Aethyl-trans-2-methyl-3-phenylglycidat Linear Structure Formula: C12H14O3 Molecular Formula: C12H14O3 Molecular Weight: 206.241 Type of Substance: heterocyclic InChI Key: PTJLNEHAZVPEFQ-CMPLNLGQSA-N Note:

O

O racemate

Substance Label (2) Label References IIt

Alekseeva, L. M.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Journal of Organic Chemistry USSR (English Translation); vol. 22; nb. 9; (1986); p. 1664 - 1666; Zhurnal Organicheskoi Khimii; vol. 22; nb. 9; (1986); p. 1854 - 1857, View in Reaxys

(trans-1a)

Kagan; Firth; Journal of Organic Chemistry; vol. 39; (1974); p. 3145, View in Reaxys

Related Structure (2)

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Related Structure

References

beschriebenen, Valente; Wolfhagen; Journal of Organic Chemistry; vol. 31; (1966); p. 2509,2510,2511, View in Reaxys aus Benzaldehyd und (+-)-2-Chlorpropionsaeureaethylester mit Hilfe von Natriumamid hergestellten Praeparat (Kp&4%: 117-121grad) vorgelegen.

Diese Verbindung Blicke et al.; Journal of the American Chemical Society; vol. 76; (1954); p. 3161, View in Reaxys hat wahrscheinlich auch als Hauptbestandteil in dem im Hauptwerk (s. H 18 305) aufgefuehrten, dort als α-Methylβ-phenyl-glycidsaeure-aethylester bezeichneten Praeparat sowie in einem von.

Boiling Point (4) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

121 - 123

3

Kagan; Firth; Journal of Organic Chemistry; vol. 39; (1974); p. 3145, View in Reaxys

130

0.01

Valente; Wolfhagen; Journal of Organic Chemistry; vol. 31; (1966); p. 2509,2510,2511, View in Reaxys

117 - 121

4

MacPeek et al.; Journal of the American Chemical Society; vol. 81; (1959); p. 680,683, View in Reaxys

121

4

MacPeek et al.; Journal of the American Chemical Society; vol. 81; (1959); p. 680,683, View in Reaxys

Refractive Index (2) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Re- References fractive Index) [°C]

1.4997

589

25

Valente; Wolfhagen; Journal of Organic Chemistry; vol. 31; (1966); p.

2509,2510,2511, View in Reaxys

1.5052

589

30

MacPeek et al.; Journal of the American Chemical Society; vol. 81; (1959); p. 680,683, View in Reaxys

Density (1) 1 of 1

Density [g·cm-3]

1.0865

Measurement Tempera- 20 ture [°C] MacPeek et al.; Journal of the American Chemical Society; vol. 81; (1959); p. 680,683, View in Reaxys NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Alekseeva, L. M.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Journal of Organic Chemistry USSR (English Translation); vol. 22; nb. 9; (1986); p. 1664 - 1666; Zhurnal Organicheskoi Khimii; vol. 22; nb. 9; (1986); p. 1854 - 1857, View in Reaxys

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2 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Alekseeva, L. M.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Journal of Organic Chemistry USSR (English Translation); vol. 22; nb. 9; (1986); p. 1664 - 1666; Zhurnal Organicheskoi Khimii; vol. 22; nb. 9; (1986); p. 1854 - 1857, View in Reaxys 3 of 4

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-13C.

Alekseeva, L. M.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Journal of Organic Chemistry USSR (English Translation); vol. 22; nb. 9; (1986); p. 1664 - 1666; Zhurnal Organicheskoi Khimii; vol. 22; nb. 9; (1986); p. 1854 - 1857, View in Reaxys 4 of 4

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

1H

Kagan; Firth; Journal of Organic Chemistry; vol. 39; (1974); p. 3145, View in Reaxys

Reaxys ID 4138973 View in Reaxys

O

4/30 CAS Registry Number: 7042-28-6; 7141-24-4; 41232-97-7 Chemical Name: Aethyl-cis-2-methyl-3-phenylglycidat Linear Structure Formula: C12H14O3 Molecular Formula: C12H14O3 Molecular Weight: 206.241 Type of Substance: heterocyclic InChI Key: PTJLNEHAZVPEFQ-ZYHUDNBSSA-N Note:

O

O racemate

Substance Label (3) Label References IIc

Alekseeva, L. M.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Journal of Organic Chemistry USSR (English Translation); vol. 22; nb. 9; (1986); p. 1664 - 1666; Zhurnal Organicheskoi Khimii; vol. 22; nb. 9; (1986); p. 1854 - 1857, View in Reaxys

(Z)-2-Methyl-3phenylglycidat 1

Kagan,J. et al.; Journal of Organic Chemistry; vol. 42; nb. 2; (1977); p. 343 - 344, View in Reaxys

(cis-1a)

Kagan; Firth; Journal of Organic Chemistry; vol. 39; (1974); p. 3145, View in Reaxys

Boiling Point (1) Boiling Point [°C] 97 - 99

Pressure (Boiling Point) [Torr]

References

0.5

Kagan; Firth; Journal of Organic Chemistry; vol. 39; (1974); p. 3145, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy)

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Alekseeva, L. M.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Journal of Organic Chemistry USSR (English Translation); vol. 22; nb. 9; (1986); p. 1664 - 1666; Zhurnal Organicheskoi Khimii; vol. 22; nb. 9; (1986); p. 1854 - 1857, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Alekseeva, L. M.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Journal of Organic Chemistry USSR (English Translation); vol. 22; nb. 9; (1986); p. 1664 - 1666; Zhurnal Organicheskoi Khimii; vol. 22; nb. 9; (1986); p. 1854 - 1857, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-13C.

Alekseeva, L. M.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Journal of Organic Chemistry USSR (English Translation); vol. 22; nb. 9; (1986); p. 1664 - 1666; Zhurnal Organicheskoi Khimii; vol. 22; nb. 9; (1986); p. 1854 - 1857, View in Reaxys

Reaxys ID 4141178 View in Reaxys

O

5/30 CAS Registry Number: 40956-36-3; 40956-37-4 Chemical Name: t-butyl (Z)-2-methyl-3-phenylglicidate; tert.-Butyl-(Z)-2-methyl-3-phenyloxirancarboxylat Linear Structure Formula: C14H18O3 Molecular Formula: C14H18O3 Molecular Weight: 234.295 Type of Substance: heterocyclic InChI Key: JKGZBHVVOWPVKW-FZMZJTMJSA-N Note:

O

O racemate

Substance Label (2) Label References (Z) 1g

Jonczyk, Andrzej; Zomerfeld, Tomasz; Tetrahedron Letters; vol. 44; nb. 11; (2003); p. 2359 - 2361, View in Reaxys

(Z-2c)

Dagli; Wemple; Journal of Organic Chemistry; vol. 39; (1974); p. 2938, View in Reaxys

Boiling Point (1) Boiling Point [°C] 100 - 104

Pressure (Boiling Point) [Torr]

References

0.8

Jonczyk, Andrzej; Zomerfeld, Tomasz; Tetrahedron Letters; vol. 44; nb. 11; (2003); p.

2359 - 2361, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Jonczyk, Andrzej; Zomerfeld, Tomasz; Tetrahedron Letters; vol. 44; nb. 11; (2003); p. 2359 - 2361, View in Reaxys

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Reaxys ID 4141179 View in Reaxys

6/30 CAS Registry Number: 40956-36-3; 40956-37-4 Chemical Name: tert.-Butyl-(E)-2-methyl-3-phenyloxirancarboxylat Linear Structure Formula: C14H18O3 Molecular Formula: C14H18O3 Molecular Weight: 234.295 Type of Substance: heterocyclic InChI Key: JKGZBHVVOWPVKW-RISCZKNCSA-N Note:

O

O

O racemate

Substance Label (2) Label References (E) 1g ester

Jonczyk, Andrzej; Zomerfeld, Tomasz; Tetrahedron Letters; vol. 44; nb. 11; (2003); p. 2359 - 2361, View in Reaxys

(E-2c)

Dagli; Wemple; Journal of Organic Chemistry; vol. 39; (1974); p. 2938, View in Reaxys

Reaxys ID 4676675 View in Reaxys

O

7/30 CAS Registry Number: 40956-32-9; 40956-33-0; 80532-66-7; 92817-32-8 Chemical Name: (Z)-methyl 2-methyl-3-phenyl-2-oxiranecarboxylate Linear Structure Formula: C11H12O3 Molecular Formula: C11H12O3 Molecular Weight: 192.214 Type of Substance: heterocyclic InChI Key: CPPPKJUXIISPJL-MWLCHTKSSA-N Note:

O

O racemate

Substance Label (1) Label References E-III

Anisimova, O. S.; Chistyakov, V. V.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 22; nb. 10; (1986); p. 1058 - 1063; Khimiya Geterotsiklicheskikh Soedinenii; vol. 22; nb. 10; (1986); p. 1310 - 1314, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Johnson, Carl R.; Bade, Thomas R.; Journal of Organic Chemistry; vol. 47; nb. 7; (1982); p. 1205 - 1212, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) fragmentation pat- Anisimova, O. S.; Chistyakov, V. V.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Chemistry of Hetertern; spectrum; ocyclic Compounds (New York, NY, United States); vol. 22; nb. 10; (1986); p. 1058 - 1063; Khimiya Geterotelectron impact siklicheskikh Soedinenii; vol. 22; nb. 10; (1986); p. 1310 - 1314, View in Reaxys (EI)

Reaxys ID 4676676 View in Reaxys

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8/30

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CAS Registry Number: 40956-32-9; 40956-33-0; 80532-66-7; 92817-32-8 Chemical Name: (E)-methyl 2-methyl-3-phenyl-2-oxiranecarboxylate Linear Structure Formula: C11H12O3 Molecular Formula: C11H12O3 Molecular Weight: 192.214 Type of Substance: heterocyclic InChI Key: CPPPKJUXIISPJL-GXSJLCMTSA-N Note:

O

O

O racemate

Substance Label (1) Label References Table I, No. 6

Ayi, A. I.; Remli, M.; Condom, R.; Guedj, R.; Journal of Fluorine Chemistry; vol. 17; (1981); p. 565 - 580, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Johnson, Carl R.; Bade, Thomas R.; Journal of Organic Chemistry; vol. 47; nb. 7; (1982); p. 1205 - 1212, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CCl4 scopy) Ayi, A. I.; Remli, M.; Condom, R.; Guedj, R.; Journal of Fluorine Chemistry; vol. 17; (1981); p. 565 - 580, View in Reaxys

Reaxys ID 6143687 View in Reaxys

O

9/30 Chemical Name: t-butyl β-phenyl-α-methylglycidate; (E/Z)-t-butyl 2-methyl-3-phenylglycidate Linear Structure Formula: C14H18O3 Molecular Formula: C14H18O3 Molecular Weight: 234.295 Type of Substance: heterocyclic InChI Key: JKGZBHVVOWPVKW-UHFFFAOYSA-N Note:

O

O

Substance Label (2) Label References (E+Z) 1g

Jonczyk, Andrzej; Zomerfeld, Tomasz; Tetrahedron Letters; vol. 44; nb. 11; (2003); p. 2359 - 2361, View in Reaxys

VI

Bansal, Raj, K.; Shrama, Vino K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 31; nb. 8; (1992); p. 521 - 523, View in Reaxys

Boiling Point (1) Boiling Point [°C] 150 - 152

Pressure (Boiling Point) [Torr]

References

5

Bansal, Raj, K.; Shrama, Vino K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 31; nb. 8; (1992); p. 521 - 523, View in Reaxys

Refractive Index (1)

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Refractive Index

Wavelength (Refractive Index) [nm]

Temperature (Re- References fractive Index) [°C]

1.486

589

37

Bansal, Raj, K.; Shrama, Vino K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 31; nb.

8; (1992); p. 521 - 523, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Bansal, Raj, K.; Shrama, Vino K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 31; nb. 8; (1992); p. 521 - 523, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

1740 cm**(-1)

Bansal, Raj, K.; Shrama, Vino K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 31; nb. 8; (1992); p. 521 - 523, View in Reaxys

Reaxys ID 1379633 View in Reaxys

O

10/30 CAS Registry Number: 40956-36-3; 40956-37-4 Linear Structure Formula: C14H18O3 Molecular Formula: C14H18O3 Molecular Weight: 234.295 Type of Substance: heterocyclic InChI Key: JKGZBHVVOWPVKW-FZMZJTMJSA-N Note:

O

O

Substance Label (1) Label References Oxiran 7b

d'Incan; Seyden-Penne; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 281; (1975); p. 1031, View in Reaxys

Reaxys ID 1383003 View in Reaxys

O

11/30 CAS Registry Number: 52123-63-4; 52123-64-5 Chemical Name: Aethyl-2-methyl-3-deuterio-3-phenylglycidat Linear Structure Formula: C12H13DO3 Molecular Formula: C12H14O3 Molecular Weight: 207.233 Type of Substance: heterocyclic InChI Key: PTJLNEHAZVPEFQ-MMIHMFRQSA-N Note:

O 2H

O

Substance Label (1) Label References (1b)

Kagan; Firth; Journal of Organic Chemistry; vol. 39; (1974); p. 3145, View in Reaxys

Boiling Point (1)

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Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

120 - 125

3

Kagan; Firth; Journal of Organic Chemistry; vol. 39; (1974); p. 3145, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

1H

Kagan; Firth; Journal of Organic Chemistry; vol. 39; (1974); p. 3145, View in Reaxys

Reaxys ID 4676674 View in Reaxys

12/30 CAS Registry Number: 40956-32-9; 40956-33-0; 80532-66-7; 92817-32-8 Linear Structure Formula: C11H12O3 Molecular Formula: C11H12O3 Molecular Weight: 192.214 Type of Substance: heterocyclic InChI Key: CPPPKJUXIISPJL-UMJHXOGRSA-N Note:

O

O

O

Substance Label (1) Label References Z-III

Anisimova, O. S.; Chistyakov, V. V.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 22; nb. 10; (1986); p. 1058 - 1063; Khimiya Geterotsiklicheskikh Soedinenii; vol. 22; nb. 10; (1986); p. 1310 - 1314, View in Reaxys

Mass Spectrometry (1) Description (Mass References Spectrometry) fragmentation pat- Anisimova, O. S.; Chistyakov, V. V.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Chemistry of Hetertern; spectrum; ocyclic Compounds (New York, NY, United States); vol. 22; nb. 10; (1986); p. 1058 - 1063; Khimiya Geterotelectron impact siklicheskikh Soedinenii; vol. 22; nb. 10; (1986); p. 1310 - 1314, View in Reaxys (EI)

Reaxys ID 4683432 View in Reaxys

O

13/30 CAS Registry Number: 7042-28-6; 7141-24-4; 41232-97-7 Linear Structure Formula: C12H14O3 Molecular Formula: C12H14O3 Molecular Weight: 206.241 Type of Substance: heterocyclic InChI Key: PTJLNEHAZVPEFQ-KFJBMODSSA-N Note:

O

O

Substance Label (2) Label References E-II

Anisimova, O. S.; Chistyakov, V. V.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 22; nb. 10; (1986); p. 1058 - 1063; Khimiya Geterotsiklicheskikh Soedinenii; vol. 22; nb. 10; (1986); p. 1310 - 1314, View in Reaxys

Z-II

Anisimova, O. S.; Chistyakov, V. V.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 22; nb. 10; (1986); p. 1058 - 1063; Khimiya Geterotsiklicheskikh Soedinenii; vol. 22; nb. 10; (1986); p. 1310 - 1314, View in Reaxys

Mass Spectrometry (1) Description (Mass References Spectrometry)

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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fragmentation pat- Anisimova, O. S.; Chistyakov, V. V.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Chemistry of Hetertern; spectrum; ocyclic Compounds (New York, NY, United States); vol. 22; nb. 10; (1986); p. 1058 - 1063; Khimiya Geterotelectron impact siklicheskikh Soedinenii; vol. 22; nb. 10; (1986); p. 1310 - 1314, View in Reaxys (EI)

Reaxys ID 8544994 View in Reaxys

O

14/30 Linear Structure Formula: C12H14O3 Molecular Formula: C12H14O3 Molecular Weight: 206.241 Type of Substance: heterocyclic InChI Key: PTJLNEHAZVPEFQ-ZYHUDNBSSA-N Note:

O

O

Substance Label (1) Label References cis-4a

Kiyooka, Syun-Ichi; Shahid, Kazi A.; Tetrahedron Asymmetry; vol. 11; nb. 7; (2000); p. 1537 - 1542, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Kiyooka, Syun-Ichi; Shahid, Kazi A.; Tetrahedron Asymmetry; vol. 11; nb. 7; (2000); p. 1537 - 1542, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Kiyooka, Syun-Ichi; Shahid, Kazi A.; Tetrahedron Asymmetry; vol. 11; nb. 7; (2000); p. 1537 - 1542, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Kiyooka, Syun-Ichi; Shahid, Kazi A.; Tetrahedron Asymmetry; vol. 11; nb. 7; (2000); p. 1537 - 1542, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Kiyooka, Syun-Ichi; Shahid, Kazi A.; Tetrahedron Asymmetry; vol. 11; nb. 7; (2000); p. 1537 - 1542, View in Reaxys

Reaxys ID 10658558 View in Reaxys

O

15/30 CAS Registry Number: 928826-51-1 Linear Structure Formula: C12H14O3 Molecular Formula: C12H14O3 Molecular Weight: 206.241 Type of Substance: heterocyclic InChI Key: PTJLNEHAZVPEFQ-CMPLNLGQSA-N Note:

O O

Substance Label (1) Label References 6l

Chen, Zhihua; Morimoto, Hiroyuki; Matsunaga, Shigeki; Shibasaki, Masakatsu; Synlett; nb. 20; (2006); p.

3529 - 3532, View in Reaxys

Reaxys ID 19462855 View in Reaxys O

16/30 Linear Structure Formula: C12H14O3 Molecular Formula: C12H14O3 Molecular Weight: 206.241 InChI Key: PTJLNEHAZVPEFQ-UHFFFAOYSA-N Note:

O trans O trans trans trans

(+)-enantiomer

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.87 g/100ml

Enantiomeric excess [%ee]

86

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

51.6

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

25

Location

supporting information

Wang, Bin; Wu, Xin-Yan; Wong, O. Andrea; Nettles, Brian; Zhao, Mei-Xin; Chen, Dajun; Shi, Yian; Journal of Organic Chemistry; vol. 74; nb. 10; (2009); p. 3986 - 3989, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy)

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Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Wang, Bin; Wu, Xin-Yan; Wong, O. Andrea; Nettles, Brian; Zhao, Mei-Xin; Chen, Dajun; Shi, Yian; Journal of Organic Chemistry; vol. 74; nb. 10; (2009); p. 3986 - 3989, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

75

Location

supporting information

Wang, Bin; Wu, Xin-Yan; Wong, O. Andrea; Nettles, Brian; Zhao, Mei-Xin; Chen, Dajun; Shi, Yian; Journal of Organic Chemistry; vol. 74; nb. 10; (2009); p. 3986 - 3989, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Mid IR (MIR); Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Wang, Bin; Wu, Xin-Yan; Wong, O. Andrea; Nettles, Brian; Zhao, Mei-Xin; Chen, Dajun; Shi, Yian; Journal of Organic Chemistry; vol. 74; nb. 10; (2009); p. 3986 - 3989, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) HRMS (High reso- supporting inforlution mass spec- mation trometry)

Comment (Mass Spectrometry)

References

mol peak

Wang, Bin; Wu, Xin-Yan; Wong, O. Andrea; Nettles, Brian; Zhao, Mei-Xin; Chen, Dajun; Shi, Yian; Journal of Organic Chemistry; vol.

74; nb. 10; (2009); p. 3986 - 3989, View in Reaxys

Reaxys ID 19462859 View in Reaxys

17/30 Linear Structure Formula: C12H14O3 Molecular Formula: C12H14O3 Molecular Weight: 206.241 InChI Key: PTJLNEHAZVPEFQ-UHFFFAOYSA-N Note:

trans transtrans O O trans O (-)-enantiomer

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Wang, Bin; Wu, Xin-Yan; Wong, O. Andrea; Nettles, Brian; Zhao, Mei-Xin; Chen, Dajun; Shi, Yian; Journal of Organic Chemistry; vol. 74; nb. 10; (2009); p. 3986 - 3989, View in Reaxys

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2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

75

Location

supporting information

Wang, Bin; Wu, Xin-Yan; Wong, O. Andrea; Nettles, Brian; Zhao, Mei-Xin; Chen, Dajun; Shi, Yian; Journal of Organic Chemistry; vol. 74; nb. 10; (2009); p. 3986 - 3989, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Mid IR (MIR); Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Wang, Bin; Wu, Xin-Yan; Wong, O. Andrea; Nettles, Brian; Zhao, Mei-Xin; Chen, Dajun; Shi, Yian; Journal of Organic Chemistry; vol. 74; nb. 10; (2009); p. 3986 - 3989, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) HRMS (High reso- supporting inforlution mass spec- mation trometry)

Comment (Mass Spectrometry)

References

mol peak

Wang, Bin; Wu, Xin-Yan; Wong, O. Andrea; Nettles, Brian; Zhao, Mei-Xin; Chen, Dajun; Shi, Yian; Journal of Organic Chemistry; vol.

74; nb. 10; (2009); p. 3986 - 3989, View in Reaxys

Reaxys ID 21547788 View in Reaxys

O

18/30 Linear Structure Formula: C11H12O3 Molecular Formula: C11H12O3 Molecular Weight: 192.214 InChI Key: CPPPKJUXIISPJL-GXSJLCMTSA-N Note:

O O

Reaxys ID 21547789 View in Reaxys

O

19/30 Linear Structure Formula: C11H12O3 Molecular Formula: C11H12O3 Molecular Weight: 192.214 InChI Key: CPPPKJUXIISPJL-KOLCDFICSA-N Note:

O O

Reaxys ID 21720896 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

20/30

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O

CAS Registry Number: 906425-78-3 Chemical Name: NSC195114 Linear Structure Formula: C16H22O3 Molecular Formula: C16H22O3 Molecular Weight: 262.349 InChI Key: HJASZXNFBZQHLE-UHFFFAOYSA-N Note:

O

O

Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Habash, Maha; Taha, Mutasem O.; Bioorganic and Medicinal Chemistry; vol. 19; nb. 16; (2011); p. 4746 - 4771, View in Reaxys 2 of 3

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

muscle glycogen phosphorylase a-form of rabbit

Concentration (Pharmacological Data)

10 μmol/l

Kind of Dosing (Pharma- title comp. dissolved in DMSO cological Data) Further Details (Pharma- in vitro GP enzyme inhibition assay cological Data) Type (Pharmacological Data)

inhibition rate

Value of Type (Pharmacological Data)

23 percent

Habash, Maha; Taha, Mutasem O.; Bioorganic and Medicinal Chemistry; vol. 19; nb. 16; (2011); p. 4746 - 4771, View in Reaxys 3 of 3

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

muscle glycogen phosphorylase a-form of rabbit

Concentration (Pharmacological Data)

10 μmol/l

Kind of Dosing (Pharma- title comp. dissolved in DMSO cological Data) Further Details (Pharma- in vitro GP enzyme inhibition assay cological Data) Results

molecular target: rabbit glycogen phosphorylase a-form

Habash, Maha; Taha, Mutasem O.; Bioorganic and Medicinal Chemistry; vol. 19; nb. 16; (2011); p. 4746 - 4771, View in Reaxys

Reaxys ID 27712006 View in Reaxys

O

21/30 Linear Structure Formula: C16H22O3 Molecular Formula: C16H22O3 Molecular Weight: 262.349 InChI Key: VPLUBWAYTPDNQM-XJKSGUPXSA-N Note:

O O

rel-configuration

Substance Label (1)

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Label

References

2b

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 7805, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties colourless

supporting information

References Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb.

35; (2014); p. 7803 - 7805, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

22.84

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

23.74

Frequency (NMR Spectroscopy) [MHz]

126

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); spectrum

References Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb.

35; (2014); p. 7803 - 7805, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Reaxys ID 27712007 View in Reaxys

O

22/30 Linear Structure Formula: C16H22O3 Molecular Formula: C16H22O3 Molecular Weight: 262.349 InChI Key: VPLUBWAYTPDNQM-XJKSGUPXSA-N Note:

O O

Substance Label (1) Label References 2b

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 7805, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

22.84

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

23.74

Frequency (NMR Spectroscopy) [MHz]

126

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); elec-

supporting information

References Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb.

35; (2014); p. 7803 - 7805, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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trospray ionisation (ESI); spectrum

Reaxys ID 27712009 View in Reaxys

O

23/30 Linear Structure Formula: C16H22O3 Molecular Formula: C16H22O3 Molecular Weight: 262.349 InChI Key: VPLUBWAYTPDNQM-CJNGLKHVSA-N Note:

O O

Substance Label (1) Label References 2b

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 7805, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

22.84

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

23.74

Frequency (NMR Spectroscopy) [MHz]

126

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); spectrum

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb.

35; (2014); p. 7803 - 7805, View in Reaxys

Reaxys ID 27712010 View in Reaxys

24/30 Linear Structure Formula: C14H18O3 Molecular Formula: C14H18O3 Molecular Weight: 234.295 InChI Key: JKGZBHVVOWPVKW-RISCZKNCSA-N Note:

O O O rel-configuration

Substance Label (1) Label References 2a

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 7805, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties colourless

supporting information

References Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb.

35; (2014); p. 7803 - 7805, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

22.74

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

24.04

Frequency (NMR Spectroscopy) [MHz]

126

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys IR Spectroscopy (1)

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); spectrum

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb.

35; (2014); p. 7803 - 7805, View in Reaxys

Reaxys ID 27712011 View in Reaxys

O

25/30 Linear Structure Formula: C17H24O3 Molecular Formula: C17H24O3 Molecular Weight: 276.376 InChI Key: TVAZPLORKCBRFN-SUMWQHHRSA-N Note:

O O

rel-configuration

Substance Label (1) Label References 2c

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 7805, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties colourless

supporting information

References Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb.

35; (2014); p. 7803 - 7805, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

23.04

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

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Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

23.84

Frequency (NMR Spectroscopy) [MHz]

126

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); spectrum

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb.

35; (2014); p. 7803 - 7805, View in Reaxys

Reaxys ID 27712012 View in Reaxys

O

26/30 Linear Structure Formula: C13H16O3 Molecular Formula: C13H16O3 Molecular Weight: 220.268 InChI Key: MBUVFJMZFCDGOV-WCQYABFASA-N Note:

O O

Substance Label (1) Label References 2d

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 7805, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

23.74

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

22.94

Frequency (NMR Spectroscopy) [MHz]

126

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); spectrum

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb.

35; (2014); p. 7803 - 7805, View in Reaxys

Reaxys ID 27712015 View in Reaxys

O

27/30 Linear Structure Formula: C13H16O3 Molecular Formula: C13H16O3 Molecular Weight: 220.268 InChI Key: MBUVFJMZFCDGOV-YPMHNXCESA-N Note:

O O

Substance Label (1) Label References 2d

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 7805, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy)

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Temperature (NMR Spectroscopy) [°C]

23.74

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

22.94

Frequency (NMR Spectroscopy) [MHz]

126

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); spectrum

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb.

35; (2014); p. 7803 - 7805, View in Reaxys

Reaxys ID 27712017 View in Reaxys

28/30 Linear Structure Formula: C17H24O3 Molecular Formula: C17H24O3 Molecular Weight: 276.376 InChI Key: CDKDNDWUQCZWFV-ZBFHGGJFSA-N Note:

O O O rel-configuration

Substance Label (1) Label References 2e

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 7805, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties

References

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

25/29

2016-02-16 07:02:28

colourless

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb.

35; (2014); p. 7803 - 7805, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

22.94

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

24.04

Frequency (NMR Spectroscopy) [MHz]

126

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); spectrum

References Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb.

35; (2014); p. 7803 - 7805, View in Reaxys

Reaxys ID 27712020 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

29/30

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O

Linear Structure Formula: C19H28O3 Molecular Formula: C19H28O3 Molecular Weight: 304.43 InChI Key: WLVLOFWJCFKUNQ-IFXJQAMLSA-N Note:

O O

Substance Label (1) Label References 2f

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 7805, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

22.74

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

24.04

Frequency (NMR Spectroscopy) [MHz]

126

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); elec-

supporting information

References Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb.

35; (2014); p. 7803 - 7805, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

27/29

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trospray ionisation (ESI); spectrum

Reaxys ID 27712021 View in Reaxys

O

30/30 Linear Structure Formula: C19H28O3 Molecular Formula: C19H28O3 Molecular Weight: 304.43 InChI Key: WLVLOFWJCFKUNQ-KUHUBIRLSA-N Note:

O O

Substance Label (1) Label References 2f

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 7805, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

22.74

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

24.04

Frequency (NMR Spectroscopy) [MHz]

126

Location

supporting information

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

28/29

2016-02-16 07:02:28

Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); spectrum

References Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb.

35; (2014); p. 7803 - 7805, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

29/29

2016-02-16 07:02:28