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1. Query
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Date
1 substances in Reaxys
2017-10-15 00h:07m:23s (EST)
OH
Search as: As drawn, No salts, No mixtures, No isotopes, No charges, No radicals
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Reaxys ID 2041323 View in Reaxys
1/1 CAS Registry Number: 1641-41-4 Chemical Name: 4-indanol; 2,3-dihydro-1H-inden-4-ol; 4-hydroxyindane; 7-hydroxyindan; indan-4-ol; 4-Hydroxy-indan; 4Oxy-hydrinden Linear Structure Formula: C9H10O Molecular Formula: C9H10O Molecular Weight: 134.178 Type of Substance: isocyclic InChI Key: DPHNJPUOMLRELT-UHFFFAOYSA-N Note:
OH
Substance Label (17) Label References 3a
Patent; DAIICHI SANKYO COMPANY, LIMITED; SONI, Ajay; AGARWAL, Aditi; DESHMUKH, Sangram Shesharao; PURNAPATRE, Kedar Padmakar; MARUMOTO, Shinji; (76 pag.); WO2016/1834; (2016); (A1) English, View in Reaxys
3j
Yuan, Changxia; Liang, Yong; Hernandez, Taylor; Berriochoa, Adrian; Houk, Kendall N.; Siegel, Dionicio; Nature; vol. 499; nb. 7457; (2013); p. 192 - 196, View in Reaxys; Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; AXELROD, Abram; JOHNSON, Trevor, C.; SIEGEL, Dionicio; CAMELIO, Andrew, M.; YUAN, Changxia; ELIASEN, Anders; WO2014/158209; (2014); (A1) English, View in Reaxys
54
Onyango, Evans O.; Jacobi, Peter A.; Journal of Organic Chemistry; vol. 77; nb. 17; (2012); p. 7411 - 7427, View in Reaxys
I-IIIb
Patent; InterMune, Inc.; US2011/152246; (2011); (A1) English, View in Reaxys
10
Becker,A.R. et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 5058 - 5068, View in Reaxys; Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; LEE, Kuo-Hsiung; DONG, Yizhou; SHI, Qian; BASTOW, Kenneth, F.; WO2010/80414; (2010); (A2) English, View in Reaxys
1
Bratton, Larry D.; Filzen, Gary F.; Geyer, Andrew; Hoffman, Jennifer K.; Lu, Gina; Pulaski, Jim; Trivedi, Bharat K.; Unangst, Paul C.; Xu, Xiangyang; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 13; (2007); p. 3624 - 3629, View in Reaxys
4a
Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham; Journal of Organic Chemistry; vol. 71; nb. 11; (2006); p. 4130 - 4140, View in Reaxys
2i
Odedra, Arjan; Wu, Chang-Jung; Pratap, Taduri Bhanu; Huang, Chun-Wei; Ran, Ying-Fen; Liu, RaiShung; Journal of the American Chemical Society; vol. 127; nb. 10; (2005); p. 3406 - 3412, View in Reaxys
4c
Lowe III, John A.; Qian, Weimin; Drozda, Susan E.; Volkmann, Robert A.; Nason, Deane; Nelson, Robert B.; Nolan, Charles; Liston, Dane; Ward, Karen; Faraci, Steve; Verdries, Kim; Seymour, Pat; Majchrzak, Michael; Villalobos, Anabella; White, W. Frost; Journal of Medicinal Chemistry; vol. 47; nb. 6; (2004); p. 1575 - 1586, View in Reaxys
3 (Ar1=4-indanyl)
Gilbert, Adam M.; Coleman, Thomas; Kodah, Jason; Mewshaw, Richard E.; Scerni, Rosemary; Schechter, Lee E.; Smith, Deborah L.; Andree, Terrance H.; Bioorganic and Medicinal Chemistry Letters; vol. 14; nb. 21; (2004); p. 5281 - 5284, View in Reaxys
2
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/41275; (2004); (A1) English, View in Reaxys
12A
Patent; Auerbach, Bruce J.; Bratton, Larry D.; Filzen, Gary F.; Geyer, Andrew G.; Trivedi, Bharat K.; Unangst, Paul C.; US2003/225158; (2003); (A1) English, View in Reaxys
42a
Dieter; Lin; Journal of Organic Chemistry; vol. 49; nb. 17; (1984); p. 3183 - 3195, View in Reaxys
Tab. I
Buchanan, Michelle V.; Analytical Chemistry; vol. 56; nb. 3; (1984); p. 546 - 549, View in Reaxys
II
Bruice et al.; Journal of the American Chemical Society; vol. 95; (1973); p. 1673, View in Reaxys
1d
Dallacker,F.; Van Werst,J.; Chemische Berichte; vol. 105; (1972); p. 2565 - 2574, View in Reaxys
XIII
Novak; Protiva; Collection of Czechoslovak Chemical Communications; vol. 23; (1958); p. 663,666, 671, View in Reaxys
Patent-Specific Data (2) Location in Patent References Page/Page column
Patent; Janssen Pharmaceutica NV; Sui, Zhihua; Cai, Chaozhong; Zhang, Xuqing; US2014/275179; (2014); (A1) English, View in Reaxys; Patent; Janssen Pharmaceutica NV; Illig, Carl R.; Player, Mark R.; Zhang, Xuqing; US9067898; (2015); (B1) English, View in Reaxys
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Patent; Auerbach, Bruce J.; Bratton, Larry D.; Filzen, Gary F.; Geyer, Andrew G.; Trivedi, Bharat K.; Unangst, Paul C.; US2003/225158; (2003); (A1) English, View in Reaxys Druglikeness (1) 1 of 1
LogP
2.298
H Bond Donors
1
H Bond Acceptors
0
Rotatable Bonds
0
TPSA
20.23
Lipinski Number
4
Veber Number
2
Derivative (8) Comment (Derivative)
References
4-nitro-benzoyl Dean et al.; Journal of Applied Chemistry; vol. 9; (1959); p. 629,637, View in Reaxys derivative (mp: 93 degree ) phenylcarbamoyl derivative (mp: 159 degree )
Dean et al.; Journal of Applied Chemistry; vol. 9; (1959); p. 629,637, View in Reaxys
3,5-dinitro-benzoyl derivative (mp: 114 degree )
Dean et al.; Journal of Applied Chemistry; vol. 9; (1959); p. 629,637, View in Reaxys
<1>naphthylcarDean et al.; Journal of Applied Chemistry; vol. 9; (1959); p. 629,637, View in Reaxys bamoyl derivative (mp: 156 degree ) biphenyl-4-ylcar- Dean et al.; Journal of Applied Chemistry; vol. 9; (1959); p. 629,637, View in Reaxys bamoyl derivative (mp: 172 degree ) 2,4-Dinitrophenyl- Novak; Protiva; Collection of Czechoslovak Chemical Communications; vol. 23; (1958); p. 663,666, 671, hydrazon: F: View in Reaxys 241-242grad (unkorr.) phenylcarbamoyl derivative (mp: 156 degree )
Kruber; Schmieden; Chemische Berichte; vol. 72; (1939); p. 653,656, View in Reaxys; Kahles; Chemische Berichte; vol. 75; (1942); p. 1313,1315, View in Reaxys
carboxymethyl derivative (mp: 182 degree )
Kruber; Schmieden; Chemische Berichte; vol. 72; (1939); p. 653,656, View in Reaxys
Purification (1) References Karr et al.; Analytical Chemistry; vol. 32; (1960); p. 463,465, View in Reaxys Melting Point (8) 1 of 8
Melting Point [°C]
50.7 - 52.3
Becker,A.R. et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 5058 - 5068, View in Reaxys 2 of 8
Melting Point [°C]
42
Kraus; Bazant; Collection of Czechoslovak Chemical Communications; vol. 28; (1963); p. 1877,1878, View in Reaxys 3 of 8
Melting Point [°C]
50 - 50.5
Solvent (Melting Point)
pentane
Shapiro et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 3729,3730, View in Reaxys 4 of 8
Melting Point [°C]
49 - 50
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Arnold; Zaugg; Journal of the American Chemical Society; vol. 63; (1941); p. 1317,1318, View in Reaxys; Arnold et al.; Journal of the American Chemical Society; vol. 63; (1941); p. 1161, View in Reaxys 5 of 8
Melting Point [°C]
39.5 - 40
Solvent (Melting Point)
petroleum ether
Comment (Melting Point)
2. Modifikation.
Arnold; Zaugg; Journal of the American Chemical Society; vol. 63; (1941); p. 1317,1318, View in Reaxys; Arnold et al.; Journal of the American Chemical Society; vol. 63; (1941); p. 1161, View in Reaxys 6 of 8
Solvent (Melting Point)
petroleum ether
Lindner; Schmitt; Zaunbauer; Monatshefte fuer Chemie; vol. 72; (1939); p. 216,220, View in Reaxys 7 of 8
Melting Point [°C]
50
Kruber; Schmieden; Chemische Berichte; vol. 72; (1939); p. 653,656, View in Reaxys 8 of 8
Melting Point [°C]
47 - 51
Goth; Chemische Berichte; vol. 61; (1928); p. 1460, View in Reaxys Boiling Point (5) Boiling Point [°C]
Pressure (Boiling Point) [Torr]
Comment (Boiling References Point)
115 - 118
10
Dallacker,F.; Van Werst,J.; Chemische Berichte; vol. 105; (1972); p. 2565 - 2574, View in Reaxys
118 - 119
10
Kraus; Bazant; Collection of Czechoslovak Chemical Communications; vol. 28; (1963); p. 1877,1878, View in Reaxys
175
100
Jaeger; Kattwinkel; Brennstoff-Chemie; vol. 31; (1950); p. 65,77, View in Reaxys
120
12
Goth; Chemische Berichte; vol. 61; (1928); p. 1460, View in Reaxys
244 - 246
Oel.
Moschner; Chemische Berichte; vol. 34; (1901); p. 1259, View in Reaxys
Crystal Phase (2) Description (Crys- Comment (Crystal References tal Phase) Phase) Interplanar spacing Polymorphism
Hofer; Peebles; Analytical Chemistry; vol. 27; (1955); p. 1852,1853, View in Reaxys Indanol-(4) exist- Lindner; Schmitt; Zaunbauer; Monatshefte fuer Chemie; vol. 72; (1939); p. 216,220, iert in zwei Modifi- View in Reaxys kationen.
Crystal Property Description (3) Colour & Other References Properties orange
Patent; BIOTRON LIMITED; WO2006/135978; (2006); (A1) English, View in Reaxys
Nadeln
Arnold; Zaugg; Journal of the American Chemical Society; vol. 63; (1941); p. 1317,1318, View in Reaxys; Arnold et al.; Journal of the American Chemical Society; vol. 63; (1941); p. 1161, View in Reaxys
trikline Prismen
Lindner; Schmitt; Zaunbauer; Monatshefte fuer Chemie; vol. 72; (1939); p. 216,220, View in Reaxys
Dissociation Exponent (1) 1 of 1
Dissociation Exponent (pK)
10.2
Temperature (Dissociation Exponent) [°C]
25
Solvent (Dissociation Exponent)
H2O
Type (Dissociation Exponent)
thermodynamic
Orchin; Golumbic; Journal of the American Chemical Society; vol. 71; (1949); p. 4151, View in Reaxys Liquid/Liquid Systems (MCS) (1)
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1 of 1
Description (Liquid/ Liquid Systems (MCS))
Distribution between solvent 1 + 2
Saha et al.; Journal of Chemical and Engineering Data; vol. 8; (1963); p. 405, View in Reaxys NMR Spectroscopy (14) 1 of 14
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1H NMR (400 MHz, CDCl ): 7.02 (m, 1H), 6.80 (d, J=5.2 Hz, 1H), 6.61 (m, 1H), 2.91 (m, 3 4H), 2.05 (m, 2H).
Location
Page/Page column 119
Comment (NMR Spectroscopy)
Signals given
Patent; InterMune, Inc.; US2011/152246; (2011); (A1) English, View in Reaxys 2 of 14
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Yoshida, Kazuhiro; Takahashi, Hidetoshi; Imamoto, Tsuneo; Chemistry - A European Journal; vol. 14; nb. 27; (2008); p. 8246 - 8261, View in Reaxys 3 of 14
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Location
supporting information
Yoshida, Kazuhiro; Takahashi, Hidetoshi; Imamoto, Tsuneo; Chemistry - A European Journal; vol. 14; nb. 27; (2008); p. 8246 - 8261, View in Reaxys 4 of 14
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Location
supporting information
Yoshida, Kazuhiro; Takahashi, Hidetoshi; Imamoto, Tsuneo; Chemistry - A European Journal; vol. 14; nb. 27; (2008); p. 8246 - 8261, View in Reaxys 5 of 14
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Yoshida, Kazuhiro; Takahashi, Hidetoshi; Imamoto, Tsuneo; Chemistry - A European Journal; vol. 14; nb. 27; (2008); p. 8246 - 8261, View in Reaxys 6 of 14
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy)
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Frequency (NMR Spectroscopy) [MHz]
300
Pettersson, Ingrid; Ebdrup, Soren; Havranek, Miroslav; Pihera, Pavel; Korinek, Marek; Mogensen, John P.; Jeppesen, Claus B.; Johansson, Eva; Sauerberg, Per; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 16; (2007); p. 4625 - 4629, View in Reaxys 7 of 14
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Odedra, Arjan; Wu, Chang-Jung; Pratap, Taduri Bhanu; Huang, Chun-Wei; Ran, Ying-Fen; Liu, Rai-Shung; Journal of the American Chemical Society; vol. 127; nb. 10; (2005); p. 3406 - 3412, View in Reaxys 8 of 14
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Odedra, Arjan; Wu, Chang-Jung; Pratap, Taduri Bhanu; Huang, Chun-Wei; Ran, Ying-Fen; Liu, Rai-Shung; Journal of the American Chemical Society; vol. 127; nb. 10; (2005); p. 3406 - 3412, View in Reaxys 9 of 14
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
150
Odedra, Arjan; Wu, Chang-Jung; Pratap, Taduri Bhanu; Huang, Chun-Wei; Ran, Ying-Fen; Liu, Rai-Shung; Journal of the American Chemical Society; vol. 127; nb. 10; (2005); p. 3406 - 3412, View in Reaxys 10 of 14
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
599.752
Odedra, Arjan; Wu, Chang-Jung; Pratap, Taduri Bhanu; Huang, Chun-Wei; Ran, Ying-Fen; Liu, Rai-Shung; Journal of the American Chemical Society; vol. 127; nb. 10; (2005); p. 3406 - 3412, View in Reaxys 11 of 14
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
150.827
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Odedra, Arjan; Wu, Chang-Jung; Pratap, Taduri Bhanu; Huang, Chun-Wei; Ran, Ying-Fen; Liu, Rai-Shung; Journal of the American Chemical Society; vol. 127; nb. 10; (2005); p. 3406 - 3412, View in Reaxys 12 of 14
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Original Text (NMR Spectroscopy)
400 MHz 1H NMR (DMSO-d6) δ 9.06 (s, 1H), 6.86 (t, 1H, J=7.8 Hz), 6.59 (d, 1H, J=7.8 Hz), 6.48 (d, 1H, J=7.8 Hz), 2.75 (t, 2H, J=7.3 Hz), 2.67 (t, 2H, J=7.3 Hz), 1.92 (m, 2H)
Comment (NMR Spectroscopy)
Signals given
Patent; Auerbach, Bruce J.; Bratton, Larry D.; Filzen, Gary F.; Geyer, Andrew G.; Trivedi, Bharat K.; Unangst, Paul C.; US2003/225158; (2003); (A1) English, View in Reaxys 13 of 14
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CCl4 scopy) Dieter; Lin; Journal of Organic Chemistry; vol. 49; nb. 17; (1984); p. 3183 - 3195, View in Reaxys 14 of 14
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CCl4 scopy) Comment (NMR Spectroscopy)
1H-1H
Dieter; Lin; Journal of Organic Chemistry; vol. 49; nb. 17; (1984); p. 3183 - 3195, View in Reaxys IR Spectroscopy (4) 1 of 4
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
neat (no solvent)
Odedra, Arjan; Wu, Chang-Jung; Pratap, Taduri Bhanu; Huang, Chun-Wei; Ran, Ying-Fen; Liu, Rai-Shung; Journal of the American Chemical Society; vol. 127; nb. 10; (2005); p. 3406 - 3412, View in Reaxys 2 of 4
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
CH2Cl2
Comment (IR Spectroscopy)
3580 - 785 cm**(-1)
Dieter; Lin; Journal of Organic Chemistry; vol. 49; nb. 17; (1984); p. 3183 - 3195, View in Reaxys 3 of 4
Description (IR Spectroscopy)
Bands
Dallacker,F.; Van Werst,J.; Chemische Berichte; vol. 105; (1972); p. 2565 - 2574, View in Reaxys 4 of 4
Description (IR Spectroscopy)
Spectrum
Solvent (IR Spectroscopy)
CS2
Comment (IR Spectroscopy)
4000 - 667 cm**(-1)
Friedel; Journal of the American Chemical Society; vol. 73; (1951); p. 2881,2883, View in Reaxys Mass Spectrometry (1)
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Description (Mass References Spectrometry) chemical ionization (CI)
Buchanan, Michelle V.; Analytical Chemistry; vol. 56; nb. 3; (1984); p. 546 - 549, View in Reaxys
UV/VIS Spectroscopy (7) 1 of 7
Description (UV/VIS Spectroscopy)
Absorption maxima
Becker,A.R. et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 5058 - 5068, View in Reaxys 2 of 7
Description (UV/VIS Spectroscopy)
Absorption maxima
Solvent (UV/VIS Spectroscopy)
cyclohexane
Absorption Maxima (UV/ 277 VIS) [nm] Barker; Hollingworth; Journal of Applied Chemistry; vol. 9; (1959); p. 16,21, View in Reaxys 3 of 7
Description (UV/VIS Spectroscopy)
Absorption maxima
Solvent (UV/VIS Spectroscopy)
sodium methanolate / methanol
Absorption Maxima (UV/ 285 VIS) [nm] Shapiro et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 3729,3730, View in Reaxys 4 of 7
Description (UV/VIS Spectroscopy)
Absorption maxima
Solvent (UV/VIS Spectroscopy)
methanol
Absorption Maxima (UV/ 269; 277 VIS) [nm] Shapiro et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 3729,3730, View in Reaxys 5 of 7
Description (UV/VIS Spectroscopy)
Absorption maxima
Solvent (UV/VIS Spectroscopy)
hexane
Absorption Maxima (UV/ 268; 270; 276 VIS) [nm] Shapiro et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 3729,3730, View in Reaxys 6 of 7
Description (UV/VIS Spectroscopy)
Spectrum
Solvent (UV/VIS Spectroscopy)
cyclohexane
Comment (UV/VIS Spectroscopy)
220 - 285 nm
Woolfolk et al.; Bur. Mines Bl.; vol. 487; (1950); p. 1,53, View in Reaxys 7 of 7
Description (UV/VIS Spectroscopy)
Spectrum
Solvent (UV/VIS Spectroscopy)
cyclohexane
Friedel,R.A.; Orchin,M.; Ultraviolet Spectra of Aromatic Compounds <New York 1951> Nr. 49, View in Reaxys Isolation from Natural Product (2) Isolation from References Natural Product
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Vorkommen in Steinkohlen-Tieftemperaturteer
Agde; Kahles; Oel und Kohle; vol. 40; (1944); p. 1,5, View in Reaxys; Kahles; Chemische Berichte; vol. 75; (1942); p. 1313,1315, View in Reaxys
Vorkommen in SteinkohlenHochtemperaturteer
Kruber; Schmieden; Chemische Berichte; vol. 72; (1939); p. 653,656, View in Reaxys
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