(S)-2-Amino-2-methyl-3-phenylpropanoic acid [C10H13NO2] by Asch

Query Query O

1. Query

Results

Date

1 substances in Reaxys

2018-03-20 14h:45m:08s (EST)

HO H 2N

Search as: As drawn AND (IDE.XRN=2803962)

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Reaxys ID 2803962 View in Reaxys

1/1 CAS Registry Number: 23239-35-2 Chemical Name: (S)-2-amino-2-methyl-3-phenylpropanoic acid; (2S)-2-Amino-2-Methyl-3-Phenylpropanoic Acid; (2S)-2amino-2-methyl-3-phenyl-propanoic acid; (S)-2-amino-2-methyl-3-phenylpropionic acid; (S)-2-amino-3-phenyl-2-methylpropanoic acid; (S)-(-)-α-methylphenylalanine; (S)-(-)-α-Methylphenylalanin Linear Structure Formula: C10H13NO2 Molecular Formula: C10H13NO2 Molecular Weight: 179.219 Type of Substance: isocyclic InChI Key: HYOWVAAEQCNGLE-JTQLQIEISA-N Note:

O HO

H 2N

Substance Label (21) Label References 4

Patent; Nagase Co., Ltd.; RIKEN; Yamamoto, Kenichiro; Kodama, Kazuya; Anzai, Kinsei; Matsuyama, Keisuke; Sasano, Arisue; Hashizume, Yoshinobu; Hume, William Yuwan; Yashio, Keiji; Nozaki, Satoshi; (75 pag.); JP2016/74605; (2016); (A) Japanese, View in Reaxys

Drabina, Pavel; Karel, Sergej; Panov, Illia; Sedlak, Milos; Tetrahedron Asymmetry; vol. 24; nb. 5-6; (2013); p. 334 - 339, View in Reaxys

Hugelshofer, Cedric L.; Mellem, Kevin T.; Myers, Andrew G.; Organic Letters; vol. 15; nb. 12; (2013); p. 3134 - 3137, View in Reaxys

(S)-10

Lee, Mijoon; Kim, Dong H.; Bioorganic and Medicinal Chemistry; vol. 8; nb. 4; (2000); p. 815 - 823, View in Reaxys; Wu, Zhong-Liu; Li, Zu-Yi; Journal of Organic Chemistry; vol. 68; nb. 6; (2003); p. 2479 2482, View in Reaxys

(S)-7

Casas, Jesus; Najera, Carmen; Sansano, Jose M.; Gonzalez, Jose; Saa, Jose M.; Vega, Manuel; Tetrahedron Asymmetry; vol. 12; nb. 5; (2001); p. 699 - 702, View in Reaxys; Badorrey, Ramon; Cativiela, Carlos; Diaz-de-Villegas, Maria D.; Galvez, Jose A.; Tetrahedron Asymmetry; vol. 14; nb. 15; (2003); p. 2201 2207, View in Reaxys

(S)-9

Wu, Zhong-Liu; Li, Zu-Yi; Chemical Communications; nb. 3; (2003); p. 386 - 387, View in Reaxys

Masaki, Yukio; Arasaki, Hideki; Iwata, Masashi; Chemistry Letters; vol. 32; nb. 1; (2003); p. 4 - 5, View in Reaxys

34a

Koch, Claus-Juergen; Simonyiova, Sona; Pabel, Joerg; Kaertner, Annerose; Polborn, Kurt; Wanner, Klaus Theodor; European Journal of Organic Chemistry; nb. 7; (2003); p. 1244 - 1263, View in Reaxys

(S)-1

Shiraiwa, Tadashi; Suzuki, Masahiro; Sakai, Yoshio; Nagasawa, Hisashi; Takatani, Kazuhiro; Noshi, Daisuke; Yamanashi, Kenji; Chemical and pharmaceutical bulletin; vol. 50; nb. 10; (2002); p. 1362 - 1366, View in Reaxys

α-MePhe

Uchino, Hiroshi; Kanai, Yoshikatsu; Kim, Do Kyung; Wempe, Michael F.; Chairoungdua, Arthit; Morimoto, Emiko; Anders; Endou, Hitoshi; Molecular Pharmacology; vol. 61; nb. 4; (2002); p. 729 - 737, View in Reaxys

Belokon, Yuri N; North, Michael; Churkina, Tatiana D; Ikonnikov, Nikolai S; Maleev, Victor I; Tetrahedron; vol. 57; nb. 13; (2001); p. 2491 - 2498, View in Reaxys

Ding, Ke; Ma, Dawei; Tetrahedron; vol. 57; nb. 30; (2001); p. 6361 - 6366, View in Reaxys

Najera, Carmen; Abellan, Tomas; Sansano, Jose M.; European Journal of Organic Chemistry; nb. 15; (2000); p. 2809 - 2820, View in Reaxys

(S)-α-Me-Phe

Belokon, Yuri N.; Kochetkov, Konstantin A.; Churkina, Tatiana D.; Ikonnikov, Nikolai S.; Chesnokov, Alexey A.; Larionov, Oleg V.; Singh, Ishwar; Parmar, Virinder S.; Vyskocil, Stepan; Kagan, Henri B.; Journal of Organic Chemistry; vol. 65; nb. 21; (2000); p. 7041 - 7048, View in Reaxys

Ma, Dawei; Ding, Ke; Organic Letters; vol. 2; nb. 16; (2000); p. 2515 - 2517, View in Reaxys

(S)-7c

Chinchilla, Rafael; Galindo, Nuria; Najera, Carmen; Synthesis; nb. 4; (1999); p. 704 - 717, View in Reaxys

19c

Achatz, Oliver; Grandl, Andrea; Wanner, Klaus Theodor; European Journal of Organic Chemistry; nb. 8; (1999); p. 1967 - 1978, View in Reaxys

(S)-4

Patel; Banerjee; Chu; Brozozowski; Nanduri; Szarka; JAOCS, Journal of the American Oil Chemists' Society; vol. 75; nb. 11; (1998); p. 1473 - 1482, View in Reaxys

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(S)-27

Bjoerkling, Fredrik; Boutelje, John; Gatenbeck, Sten; Hult, Karl; Norin, Torbjoern; Szmulik, Peter; Tetrahedron; vol. 41; nb. 7; (1985); p. 1347 - 1352, View in Reaxys

L-α-Me-Phe

Anantharamaiah, G. M.; Roeske, Roger W.; Tetrahedron Letters; vol. 23; nb. 33; (1982); p. 3335 - 3336, View in Reaxys

11a

Schoellkopf, Ulrich; Hausberg, Hans-Heinrich; Segal, Marcos; Reiter, Udo; Hoppe, Inga; et al.; Liebigs Annalen der Chemie; nb. 3; (1981); p. 439 - 458, View in Reaxys

Patent-Specific Data (2) Location in Patent References Patent; Nagase Co., Ltd.; RIKEN; Yamamoto, Kenichiro; Kodama, Kazuya; Anzai, Kinsei; Matsuyama, Keisuke; Sasano, Arisue; Hashizume, Yoshinobu; Hume, William Yuwan; Yashio, Keiji; Nozaki, Satoshi; (75 pag.); JP2016/74605; (2016); (A) Japanese, View in Reaxys Claim

Patent; University of Pittsburgh of the Commonwealth System of Higher Education; US5952294; (1999); (A1) English, View in Reaxys; Patent; University of Miami; US4690936; (1987); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

-1.269

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

63.32

Lipinski Number

Veber Number

Derivative (6) Comment (Derivative)

Derivative

References

(S)-α-methyl-phenylalanine hydrochloride

Williams; Im; Journal of the American Chemical Society; vol. 113; nb. 24; (1991); p. 9276 - 9286, View in Reaxys

(S)-α-methyl-phenylalanine hydrochloride

Belokon', Yuri N.; Chernoglazova, Nina I.; Kochetkov, Constantin A.; Garbalinskaya, Natalia S.; Belikov, Vasili M.; Journal of the Chemical Society, Chemical Communications; nb. 3; (1985); p. 171 - 172, View in Reaxys

(S)-α-methyl-phenylalanine hydrochloride

Schoellkopf, Ulrich; Hausberg, Hans-Heinrich; Segal, Marcos; Reiter, Udo; Hoppe, Inga; et al.; Liebigs Annalen der Chemie; nb. 3; (1981); p. 439 - 458, View in Reaxys

Hydrochlorid: <α>(D)20 =-1.0grad (H2O)

Kolb; Barth; Tetrahedron Letters; (1979); p. 2999,3000,3001, View in Reaxys

Hydrochlorid: F: 249grad (Zers.); <α>20(D) -8.55 (H2O)

Patent; BASF AG; DE2658942; (1978); Chem.Abstr.; vol. 89; nb. 179988, View in Reaxys

Hydrochlorid: F: 249grad (Zers.); <α>20(D): -8.55 (c = 1.03 in H2O)

Patent; BASF AG; DE2658941; (1978); Chem.Abstr.; vol. 90; nb. 23701, View in Reaxys

Purification (1) Purification (method) via reaction with (-)-chlocyphos

References Hulst, Ron; Broxterman, Quirinus B.; Kamphuis, Johan; Formaggio, Fernando; Crisma, Marco; Toniolo, Claudio; Kellogg, Richard M.; Tetrahedron Asymmetry; vol. 8; nb. 12; (1997); p. 1987 - 1999, View in Reaxys

Melting Point (7) 1 of 7

Melting Point [°C]

278 - 280

Xu, Peng-Fei; Li, Shuo; Lu, Ta-Jung; Wu, Chen-Chang; Fan, Botao; Golfis, Georgia; Journal of Organic Chemistry; vol. 71; nb. 12; (2006); p. 4364 - 4373, View in Reaxys

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2 of 7

Melting Point [°C]

276 - 279

Solvent (Melting Point)

H2O

Comment (Melting Point)

Decomposition

Melting Point [°C]

285.7

Kaptein, Bernard; Monaco, Vania; Broxterman, Quirinus B.; Schoemaker, Hans E.; Kamphuis, Johan; Recueil des Travaux Chimiques des Pays-Bas; vol. 114; nb. 4-5; (1995); p. 231 - 238, View in Reaxys 4 of 7

Melting Point [°C]

298 - 299

Belokon, Yuri N.; Bakhmutov, Vladimir I.; Chernoglazova, Nina I.; Kochetkov, Konstantin A.; Vitt, Sergei V.; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 305 - 312, View in Reaxys 5 of 7

Melting Point [°C]

308 - 309

Solvent (Melting Point)

methanol

Bjoerkling, Fredrik; Boutelje, John; Gatenbeck, Sten; Hult, Karl; Norin, Torbjoern; Szmulik, Peter; Tetrahedron; vol. 41; nb. 7; (1985); p. 1347 - 1352, View in Reaxys 6 of 7

Iwasaki; Harada; Journal of the Chemical Society. Perkin transactions 1; vol. 15; (1977); p. 1730 - 1733, View in Reaxys

7 of 7

Melting Point [°C]

279 - 280

Solvent (Melting Point)

H2O

Comment (Melting Point)

Decomposition

Turk; Panse; Marshall; The Journal of organic chemistry; vol. 40; nb. 7; (1975); p. 953 - 955, View in Reaxys Adsorption (MCS) (1) 1 of 1

Description (Adsorption (MCS))

Further physical properties of the adsorbed molecule

Solvent (Adsorption (MCS))

H2O

Temperature (Adsorption (MCS)) [°C]

Partner (Adsorption (MCS))

silica gel

Basiuk, V. A.; Gromovoy, T. Yu.; Khil'chevskaya, E. G.; Polish Journal of Chemistry; vol. 68; nb. 4; (1994); p. 777 - 782, View in Reaxys Chromatographic Data (3) Chromatographic Location data HPLC (High performance liquid chromatography)

Paragraph 0133

TLC (Thin layer chromatography) HPLC (High performance liquid chromatography)

References Patent; Nagase Co., Ltd.; RIKEN; Yamamoto, Kenichiro; Kodama, Kazuya; Anzai, Kinsei; Matsuyama, Keisuke; Sasano, Arisue; Hashizume, Yoshinobu; Hume, William Yuwan; Yashio, Keiji; Nozaki, Satoshi; (75 pag.); JP2016/74605; (2016); (A) Japanese, View in Reaxys Remelli, Maurizio; Faccini, Stefania; Conato, Chiara; Chirality; vol. 26; nb. 6; (2014); p. 313 - 318, View in Reaxys

supporting information

Hugelshofer, Cedric L.; Mellem, Kevin T.; Myers, Andrew G.; Organic Letters; vol. 15; nb. 12; (2013); p. 3134 - 3137, View in Reaxys

Circular Dichroism (1) Comment (Circu- References lar Dichroism) 195000 - 270000 nm

Yamada,S. et al.; Chemical and Pharmaceutical Bulletin; vol. 17; (1969); p. 2608 - 2613, View in Reaxys

Crystal Property Description (5)

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Colour & Other Properties

Location

References

white

Paragraph 0365

Patent; HAMARI CHEMICALS, LTD.; Moriwaki, Hiroki; Kawashima, Aki; Takeda, Ryosuke; Kawamura, Akie; Soloshonok, Vadim A.; (74 pag.); US2016/102045; (2016); (A1) English, View in Reaxys

white

Paragraph 0609

Patent; Ha mariya kuching kogok Corporation; Moriwaki, Hiroshi; Kawashima, Aki; Takeda, Ryosuke; Kawamura, Akiy; Solo, Syonok Vadim A.; (90 pag.); KR2015/133268; (2015); (A) Korean, View in Reaxys

white

supporting information

Hugelshofer, Cedric L.; Mellem, Kevin T.; Myers, Andrew G.; Organic Letters; vol. 15; nb. 12; (2013); p. 3134 - 3137, View in Reaxys

white

Lu, Ta-Jung; Lin, Cheng-Kun; Journal of Organic Chemistry; vol. 76; nb. 6; (2011); p. 1621 - 1633, View in Reaxys

white

supporting information

Green, Jonathan E.; Bender, David M.; Jackson, Stona; O'donnell, Martin J.; Mccarthy, James R.; Organic Letters; vol. 11; nb. 4; (2009); p. 807 - 810, View in Reaxys

Decomposition (3) 1 of 3

Decomposition [°C]

257 - 260

Location

supporting information

Green, Jonathan E.; Bender, David M.; Jackson, Stona; O'donnell, Martin J.; Mccarthy, James R.; Organic Letters; vol. 11; nb. 4; (2009); p. 807 - 810, View in Reaxys 2 of 3

Decomposition [°C]

298 - 300

Solvent (Decomposition) ethanol Belokon', Yu. N.; Chernoglazova, N. I.; Bakhmutov, V. I.; Garbalinskaya, N. S.; Belikov, V. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 12; (1987); p. 2595 - 2601; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1987); p. 2798 - 2804, View in Reaxys 3 of 3

Decomposition [°C]

290

Solvent (Decomposition) aq. ethanol Schoellkopf, Ulrich; Hausberg, Hans-Heinrich; Segal, Marcos; Reiter, Udo; Hoppe, Inga; et al.; Liebigs Annalen der Chemie; nb. 3; (1981); p. 439 - 458, View in Reaxys Optical Rotatory Power (28) 1 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.03 g/100ml

Enantiomeric excess [%ee]

Length of Path [cm]

Solvent (Optical Rotatory Power)

water

Optical Rotatory Power [deg]

-22.1

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

Lu, Ta-Jung; Lin, Cheng-Kun; Journal of Organic Chemistry; vol. 76; nb. 6; (2011); p. 1621 - 1633, View in Reaxys 2 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.3 g/100ml

Solvent (Optical Rotatory Power)

water

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Optical Rotatory Power [deg]

-21.7

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

Balducci, Daniele; Lazzari, Ilaria; Monari, Magda; Piccinelli, Fabio; Porzi, Gianni; Amino Acids; vol. 38; nb. 3; (2010); p. 829 - 837, View in Reaxys 3 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

water

Optical Rotatory Power [deg]

-16.1

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

Location

supporting information

Green, Jonathan E.; Bender, David M.; Jackson, Stona; O'donnell, Martin J.; Mccarthy, James R.; Organic Letters; vol. 11; nb. 4; (2009); p. 807 - 810, View in Reaxys 4 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.04 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-21.6

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

Xu, Peng-Fei; Li, Shuo; Lu, Ta-Jung; Wu, Chen-Chang; Fan, Botao; Golfis, Georgia; Journal of Organic Chemistry; vol. 71; nb. 12; (2006); p. 4364 - 4373, View in Reaxys 5 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.61 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-22

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

Wu, Zhong-Liu; Li, Zu-Yi; Journal of Organic Chemistry; vol. 68; nb. 6; (2003); p. 2479 - 2482, View in Reaxys 6 of 28

Type (Optical Rotatory Power)

[alpha]

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Concentration (Optical Rotatory Power)

0.16 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-16.1

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

Koch, Claus-Juergen; Simonyiova, Sona; Pabel, Joerg; Kaertner, Annerose; Polborn, Kurt; Wanner, Klaus Theodor; European Journal of Organic Chemistry; nb. 7; (2003); p. 1244 - 1263, View in Reaxys 7 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Length of Path [cm]

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-21.8

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

Badorrey, Ramon; Cativiela, Carlos; Diaz-de-Villegas, Maria D.; Galvez, Jose A.; Tetrahedron Asymmetry; vol. 14; nb. 15; (2003); p. 2201 - 2207, View in Reaxys 8 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.00 g/100ml

Length of Path [cm]

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-20.1

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

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.8 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-22.2

Wavelength (Optical Ro- 589 tatory Power) [nm]

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Temperature (Optical Rotatory Power) [°C]

Ding, Ke; Ma, Dawei; Tetrahedron; vol. 57; nb. 30; (2001); p. 6361 - 6366, View in Reaxys 10 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-22.1

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

Najera, Carmen; Abellan, Tomas; Sansano, Jose M.; European Journal of Organic Chemistry; nb. 15; (2000); p. 2809 - 2820, View in Reaxys 11 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.8 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-22.2

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

Ma, Dawei; Ding, Ke; Organic Letters; vol. 2; nb. 16; (2000); p. 2515 - 2517, View in Reaxys 12 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-21.5

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

Chinchilla; Falvello; Galindo; Najera; Angewandte Chemie - International Edition in English; vol. 36; nb. 9; (1997); p. 995 - 997, View in Reaxys; Chinchilla, Rafael; Galindo, Nuria; Najera, Carmen; Synthesis; nb. 4; (1999); p. 704 - 717, View in Reaxys 13 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.42 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-22.1

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

Abellan, Tomas; Najera, Carmen; Sansano, Jose M.; Tetrahedron Asymmetry; vol. 9; nb. 13; (1998); p. 2211 2214, View in Reaxys 14 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.0 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-19

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

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.0 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-21.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268, View in Reaxys 16 of 28

Patent; Abbott Laboratories; US5153358; (1992); (A1) English, View in Reaxys

17 of 28

Type (Optical Rotatory Power)

alpha

Concentration (Optical Rotatory Power)

10.4 g/l

Length of Path [cm]

Solvent (Optical Rotatory Power)

various solvent(s)

Optical Rotatory Power [deg]

-4.5

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

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

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Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-22

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

Kruizinga, Wim H.; Bolster, John; Kellogg, Richard M.; Kamphuis, Johan; Boesten, Wilhelmus H. J.; et al.; Journal of Organic Chemistry; vol. 53; nb. 8; (1988); p. 1826 - 1827, View in Reaxys 19 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.04 g/100ml

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

-4.51

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

Belokon', Yu. N.; Chernoglazova, N. I.; Bakhmutov, V. I.; Garbalinskaya, N. S.; Belikov, V. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 12; (1987); p. 2595 - 2601; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1987); p. 2798 - 2804, View in Reaxys 20 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-22

Wavelength (Optical Ro- 589 tatory Power) [nm] Bjoerkling, Fredrik; Boutelje, John; Gatenbeck, Sten; Hult, Karl; Norin, Torbjoern; Szmulik, Peter; Tetrahedron; vol. 41; nb. 7; (1985); p. 1347 - 1352, View in Reaxys 21 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.1 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-20

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

Karady, Sandor; Amato, Joseph S.; Weinstock, Leonard M.; Tetrahedron Letters; vol. 25; nb. 39; (1984); p. 4337 - 4340, View in Reaxys 22 of 28

Type (Optical Rotatory Power)

[alpha]

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Concentration (Optical Rotatory Power)

0.1 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

Wavelength (Optical Ro- 578 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Karady, Sandor; Amato, Joseph S.; Weinstock, Leonard M.; Tetrahedron Letters; vol. 25; nb. 39; (1984); p. 4337 - 4340, View in Reaxys 23 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.805 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-20.75

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

Schoellkopf, Ulrich; Hausberg, Hans-Heinrich; Segal, Marcos; Reiter, Udo; Hoppe, Inga; et al.; Liebigs Annalen der Chemie; nb. 3; (1981); p. 439 - 458, View in Reaxys 24 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.025 g/100ml

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

-4.7

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

Schoellkopf, Ulrich; Hausberg, Hans-Heinrich; Segal, Marcos; Reiter, Udo; Hoppe, Inga; et al.; Liebigs Annalen der Chemie; nb. 3; (1981); p. 439 - 458, View in Reaxys 25 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.025

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

-4.7

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

Patent; BASF AG; DE2658941; (1978); Chem.Abstr.; vol. 90; nb. 23701, View in Reaxys

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26 of 28

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

-4.7

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

Patent; BASF AG; DE2658942; (1978); Chem.Abstr.; vol. 89; nb. 179988, View in Reaxys 27 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.716 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-47.5

Wavelength (Optical Ro- 300 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Turk; Panse; Marshall; The Journal of organic chemistry; vol. 40; nb. 7; (1975); p. 953 - 955, View in Reaxys 28 of 28

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.16 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-19.74

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

Corey,E.J. et al.; Journal of the American Chemical Society; vol. 92; nb. 8; (1970); p. 2476 - 2488, View in Reaxys NMR Spectroscopy (22) 1 of 22

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

Coupling Nuclei

Solvents (NMR Spectro- water-d2 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Hugelshofer, Cedric L.; Mellem, Kevin T.; Myers, Andrew G.; Organic Letters; vol. 15; nb. 12; (2013); p. 3134 3137, View in Reaxys

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2 of 22

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

13C

Solvents (NMR Spectro- water-d2 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Hugelshofer, Cedric L.; Mellem, Kevin T.; Myers, Andrew G.; Organic Letters; vol. 15; nb. 12; (2013); p. 3134 3137, View in Reaxys 3 of 22

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

Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Lu, Ta-Jung; Lin, Cheng-Kun; Journal of Organic Chemistry; vol. 76; nb. 6; (2011); p. 1621 - 1633, View in Reaxys 4 of 22

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

13C

Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Lu, Ta-Jung; Lin, Cheng-Kun; Journal of Organic Chemistry; vol. 76; nb. 6; (2011); p. 1621 - 1633, View in Reaxys 5 of 22

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

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

300

Balducci, Daniele; Lazzari, Ilaria; Monari, Magda; Piccinelli, Fabio; Porzi, Gianni; Amino Acids; vol. 38; nb. 3; (2010); p. 829 - 837, View in Reaxys 6 of 22

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

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Balducci, Daniele; Lazzari, Ilaria; Monari, Magda; Piccinelli, Fabio; Porzi, Gianni; Amino Acids; vol. 38; nb. 3; (2010); p. 829 - 837, View in Reaxys 7 of 22

Description (NMR Spec- Chemical shifts; Spectrum troscopy)

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Green, Jonathan E.; Bender, David M.; Jackson, Stona; O'donnell, Martin J.; Mccarthy, James R.; Organic Letters; vol. 11; nb. 4; (2009); p. 807 - 810, View in Reaxys 8 of 22

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

13C

Solvents (NMR Spectro- water-d2 scopy) Location

supporting information

Green, Jonathan E.; Bender, David M.; Jackson, Stona; O'donnell, Martin J.; Mccarthy, James R.; Organic Letters; vol. 11; nb. 4; (2009); p. 807 - 810, View in Reaxys 9 of 22

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

Solvents (NMR Spectro- D2O scopy) Frequency (NMR Spectroscopy) [MHz]

400

Achatz, Oliver; Grandl, Andrea; Wanner, Klaus Theodor; European Journal of Organic Chemistry; nb. 8; (1999); p. 1967 - 1978, View in Reaxys; Xu, Peng-Fei; Li, Shuo; Lu, Ta-Jung; Wu, Chen-Chang; Fan, Botao; Golfis, Georgia; Journal of Organic Chemistry; vol. 71; nb. 12; (2006); p. 4364 - 4373, View in Reaxys 10 of 22

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- D2O scopy) Frequency (NMR Spectroscopy) [MHz]

400

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

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

300

Wu, Zhong-Liu; Li, Zu-Yi; Journal of Organic Chemistry; vol. 68; nb. 6; (2003); p. 2479 - 2482, View in Reaxys 12 of 22

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

300

Wu, Zhong-Liu; Li, Zu-Yi; Journal of Organic Chemistry; vol. 68; nb. 6; (2003); p. 2479 - 2482, View in Reaxys 13 of 22

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- D2O scopy) Frequency (NMR Spectroscopy) [MHz]

300

Ma, Dawei; Ding, Ke; Organic Letters; vol. 2; nb. 16; (2000); p. 2515 - 2517, View in Reaxys; Ding, Ke; Ma, Dawei; Tetrahedron; vol. 57; nb. 30; (2001); p. 6361 - 6366, View in Reaxys 14 of 22

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

Solvents (NMR Spectro- D2O scopy) Frequency (NMR Spectroscopy) [MHz]

300

Ma, Dawei; Ding, Ke; Organic Letters; vol. 2; nb. 16; (2000); p. 2515 - 2517, View in Reaxys; Ding, Ke; Ma, Dawei; Tetrahedron; vol. 57; nb. 30; (2001); p. 6361 - 6366, View in Reaxys 15 of 22

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

Coupling Nuclei

Solvents (NMR Spectro- D2O scopy) Chinchilla, Rafael; Galindo, Nuria; Najera, Carmen; Synthesis; nb. 4; (1999); p. 704 - 717, View in Reaxys 16 of 22

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

Solvents (NMR Spectro- D2O scopy) Bjoerkling, Fredrik; Boutelje, John; Gatenbeck, Sten; Hult, Karl; Norin, Torbjoern; Szmulik, Peter; Tetrahedron; vol. 41; nb. 7; (1985); p. 1347 - 1352, View in Reaxys; Schoellkopf, Ulrich; Hausberg, Hans-Heinrich; Segal, Marcos; Reiter, Udo; Hoppe, Inga; et al.; Liebigs Annalen der Chemie; nb. 3; (1981); p. 439 - 458, View in Reaxys; Belokon', Yu. N.; Chernoglazova, N. I.; Bakhmutov, V. I.; Garbalinskaya, N. S.; Belikov, V. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 12; (1987); p. 2595 - 2601; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1987); p. 2798 - 2804, View in Reaxys; Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268, View in Reaxys; Kaptein, Bernard; Monaco, Vania; Broxterman, Quirinus B.; Schoemaker, Hans E.; Kamphuis, Johan; Recueil des Travaux Chimiques des Pays-Bas; vol. 114; nb. 4-5; (1995); p. 231 - 238, View in Reaxys; Jung, Michael E.; D'Amico, Derin C.; Journal of the American Chemical Society; vol. 117; nb. 28; (1995); p. 7379 7388, View in Reaxys 17 of 22

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

13C

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Solvents (NMR Spectro- D2O scopy) Bjoerkling, Fredrik; Boutelje, John; Gatenbeck, Sten; Hult, Karl; Norin, Torbjoern; Szmulik, Peter; Tetrahedron; vol. 41; nb. 7; (1985); p. 1347 - 1352, View in Reaxys; Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268, View in Reaxys; Kaptein, Bernard; Monaco, Vania; Broxterman, Quirinus B.; Schoemaker, Hans E.; Kamphuis, Johan; Recueil des Travaux Chimiques des Pays-Bas; vol. 114; nb. 4-5; (1995); p. 231 - 238, View in Reaxys; Jung, Michael E.; D'Amico, Derin C.; Journal of the American Chemical Society; vol. 117; nb. 28; (1995); p. 7379 - 7388, View in Reaxys 18 of 22

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- D2O scopy) Comment (NMR Spectroscopy)

1H-1H

Bjoerkling, Fredrik; Boutelje, John; Gatenbeck, Sten; Hult, Karl; Norin, Torbjoern; Szmulik, Peter; Tetrahedron; vol. 41; nb. 7; (1985); p. 1347 - 1352, View in Reaxys; Schoellkopf, Ulrich; Hausberg, Hans-Heinrich; Segal, Marcos; Reiter, Udo; Hoppe, Inga; et al.; Liebigs Annalen der Chemie; nb. 3; (1981); p. 439 - 458, View in Reaxys; Belokon', Yu. N.; Chernoglazova, N. I.; Bakhmutov, V. I.; Garbalinskaya, N. S.; Belikov, V. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 12; (1987); p. 2595 - 2601; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1987); p. 2798 - 2804, View in Reaxys; Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268, View in Reaxys; Jung, Michael E.; D'Amico, Derin C.; Journal of the American Chemical Society; vol. 117; nb. 28; (1995); p. 7379 - 7388, View in Reaxys 19 of 22

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

Solvents (NMR Spectro- D2O scopy) Temperature (NMR Spectroscopy) [°C]

Kabuto, Kuninobu; Sasaki, Yoichi; Tetrahedron Letters; vol. 31; nb. 7; (1990); p. 1031 - 1034, View in Reaxys 20 of 22

Description (NMR Spec- NMR with shift reagents troscopy) Kabuto, Kuninobu; Sasaki, Yoichi; Tetrahedron Letters; vol. 31; nb. 7; (1990); p. 1031 - 1034, View in Reaxys

21 of 22

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

Solvents (NMR Spectro- various solvent(s); D2O scopy) Belokon, Yuri N.; Bakhmutov, Vladimir I.; Chernoglazova, Nina I.; Kochetkov, Konstantin A.; Vitt, Sergei V.; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 305 - 312, View in Reaxys 22 of 22

Description (NMR Spec- Spin-spin coupling constants troscopy) Comment (NMR Spectroscopy)

1H-1H. Solvent(s): further solvent(s), D2O

Description (IR Spectroscopy)

Intensity of IR bands; Bands

Solvent (IR Spectroscopy)

neat (no solvent, solid phase)

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Location

supporting information

Hugelshofer, Cedric L.; Mellem, Kevin T.; Myers, Andrew G.; Organic Letters; vol. 15; nb. 12; (2013); p. 3134 3137, View in Reaxys 2 of 5

Description (IR Spectroscopy)

Mid IR (MIR); Bands

Solvent (IR Spectroscopy)

potassium bromide

Location

supporting information

Green, Jonathan E.; Bender, David M.; Jackson, Stona; O'donnell, Martin J.; Mccarthy, James R.; Organic Letters; vol. 11; nb. 4; (2009); p. 807 - 810, View in Reaxys 3 of 5

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Achatz, Oliver; Grandl, Andrea; Wanner, Klaus Theodor; European Journal of Organic Chemistry; nb. 8; (1999); p. 1967 - 1978, View in Reaxys; Wu, Zhong-Liu; Li, Zu-Yi; Journal of Organic Chemistry; vol. 68; nb. 6; (2003); p. 2479 - 2482, View in Reaxys 4 of 5

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

3550 - 1654 cm**(-1)

Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268, View in Reaxys 5 of 5

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

2500 - 1590 cm**(-1)

Schoellkopf, Ulrich; Hausberg, Hans-Heinrich; Segal, Marcos; Reiter, Udo; Hoppe, Inga; et al.; Liebigs Annalen der Chemie; nb. 3; (1981); p. 439 - 458, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

supporting information

HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation)

supporting information

spectrum

Comment (Mass Spectrometry)

References Hugelshofer, Cedric L.; Mellem, Kevin T.; Myers, Andrew G.; Organic Letters; vol. 15; nb. 12; (2013); p. 3134 - 3137, View in Reaxys

mol peak

Green, Jonathan E.; Bender, David M.; Jackson, Stona; O'donnell, Martin J.; Mccarthy, James R.; Organic Letters; vol. 11; nb. 4; (2009); p. 807 - 810, View in Reaxys

FAB (fast atom bombardment); MIKE (mass ion kinetic energy)

Rimlinger, Joseph; Zanda, Matteo; Bravo, Pierfrancesco; Favretto, Donata; Traldi, Pietro; Journal of Mass Spectrometry; vol. 32; nb. 9; (1997); p. 1002 - 1007, View in Reaxys

Medchem (1) 1 of 1

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : transport; inhibition ofTarget : Xenopus laevis oocytes expressing rat LAT1 and 4F2hcBioassay : LAT1: L-type amino acid transporter 1; 4F2hc: 4F2 heavy chain oocytes incubated with 20 μmol/l L-<14C>phenylalanine and title comp. for 15 min at 22 deg C, pH 7.4; radioactivity counted by liquid scintillation spectrometry

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Substance RN

2803962View in Reaxys

Substance Name

1466770

Substance Dose

2 mM

Qualitative Results

title comp. inhibited L-<14C>phenylalanine uptake by ca. 75 percent

Measurement Parameter

Qualitative

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