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[ CAS No. 54656-96-1 ] {[proInfo.proName]}

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Chemical Structure| 54656-96-1
Chemical Structure| 54656-96-1
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Product Details of [ 54656-96-1 ]

CAS No. :54656-96-1 MDL No. :MFCD00077866
Formula : C7H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :HVOAMIOKNARIMR-LURJTMIESA-N
M.W : 123.15 Pubchem ID :10920507
Synonyms :

Calculated chemistry of [ 54656-96-1 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.17
TPSA : 33.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.31
Log Po/w (XLOGP3) : 0.37
Log Po/w (WLOGP) : 0.81
Log Po/w (MLOGP) : 0.22
Log Po/w (SILICOS-IT) : 1.35
Consensus Log Po/w : 0.81

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.26
Solubility : 6.71 mg/ml ; 0.0545 mol/l
Class : Very soluble
Log S (Ali) : -0.63
Solubility : 28.8 mg/ml ; 0.234 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.84
Solubility : 1.78 mg/ml ; 0.0145 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 54656-96-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 54656-96-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 54656-96-1 ]
  • Downstream synthetic route of [ 54656-96-1 ]

[ 54656-96-1 ] Synthesis Path-Upstream   1~31

  • 1
  • [ 1122-54-9 ]
  • [ 54656-96-1 ]
YieldReaction ConditionsOperation in experiment
>99% ee With glucose; glucose dehydrogenase from Bacillus subtilis CGMCC 1.1398; medium-chain dehydrogenase from Kuraishia capsulate CBS1993; NAD In aq. phosphate buffer for 16 h; Enzymatic reaction General procedure: Substrate scope and enantioselectivity determination The relative activities of 26 substrates were measured using thepreviously described assay protocol with adjusted ratio of enzymeand substrate concentration. The a-chloroacetophenone activitywas assumed 100percent.Enantioselectivity was determined by examining the reductionof aromatic ketones using an NADH-regeneration system consist-ing of the puried KcDH and glucose dehydrogenase (GDH) fromBacillus subtilis CGMCC 1.1398. The 1-mL reaction mixture con-tained 0.5 mM NAD+, 10 mM ketone, 1 U KcDH, 50 mg glucoseand 2 U GDH in 50 mM potassium phosphate buffer (pH 7.0). After16 h, the reaction sample was equally separated into two parts,with one terminated by adding an equal volume of methanol, fol-lowed by HPLC analysis to determine the conversion ratio, and theother extracted with ethyl acetate, followed by ee analysis. Meth-ods used for analysing chiral products using HPLC or GC aredescribed in Supplementary Table S1.
Reference: [1] Organic Letters, 2000, vol. 2, # 12, p. 1749 - 1751
[2] Synthesis, 2009, # 14, p. 2413 - 2417
[3] Advanced Synthesis and Catalysis, 2014, vol. 356, # 10, p. 2293 - 2302
[4] Tetrahedron Asymmetry, 2002, vol. 13, # 20, p. 2201 - 2204
[5] Advanced Synthesis and Catalysis, 2016, vol. 358, # 24, p. 4006 - 4018
[6] Journal of the American Chemical Society, 2014, vol. 136, # 10, p. 4031 - 4039
[7] Tetrahedron Letters, 2002, vol. 43, # 20, p. 3629 - 3631
[8] Heterocycles, 1987, vol. 26, # 12, p. 3051 - 3054
[9] Organic Letters, 2000, vol. 2, # 26, p. 4173 - 4175
[10] Chemistry - A European Journal, 2003, vol. 9, # 13, p. 2963 - 2968
[11] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 24, p. 4439 - 4444
[12] Tetrahedron: Asymmetry, 1994, vol. 5, # 7, p. 1363 - 1366
[13] Organic and Biomolecular Chemistry, 2011, vol. 9, # 15, p. 5463 - 5468
[14] Tetrahedron Letters, 2016, vol. 57, # 8, p. 899 - 904
[15] Organic Process Research and Development, 2016, vol. 20, # 8, p. 1469 - 1475
  • 2
  • [ 23389-75-5 ]
  • [ 108-22-5 ]
  • [ 54656-96-1 ]
  • [ 27854-88-2 ]
  • [ 143840-01-1 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 24, p. 8817 - 8825
  • 3
  • [ 1122-54-9 ]
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YieldReaction ConditionsOperation in experiment
78 % ee With formic acid; triethylamine In tert-butyl methyl etherInert atmosphere Triethylamine (315 mL, 2.26 mol) was added dropwise to formic acid (150 mL, 3.91 mol) with overhead stirring while maintaining the internal temperature below 60° C. with ice-bath cooling. Neat 4-acetylpyridine (100 mL, 0.904 mol) was then added rapidly while maintaining the temperature below 50° C. Following this addition, the reaction was allowed to cool to 28° C. and the chiral ruthenium catalyst [N-[(1R,2R)-2-(amino-N)-1,2-diphenylethyl]-2,4,6-trimethylbenzenesulfonamidato-N]chloro[(1,2,3,4,5,6-n)-1-methyl-4-(1-methylethyl)benzene]ruthenium (CAS No.177552-91-9; for catalyst preparation, see: Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R.; J. Am. Chem. Soc. 1996, 118, 4916-4917) (3 g, 4.46 mmol) was added. The mixture was stirred under house vacuum for 4 h and then overnight under an atmosphere of nitrogen. The reaction mixture was added dropwise to a stirred solution of 10percent Na2CO3 (4 L) and then extracted with EtOAc (3.x.1 L). The combined EtOAc layers were washed once with brine (1 L), treated with MgSO4 and Darco G-60 decolorizing charcoal and filtered through a 100 g plug of silica gel washing with 10percent MeOH/EtOAc (1 L). The filtrate was concentrated to provide a dark oil that crystallized upon standing. The solid was dissolved in warm t-butyl methyl ether (250 mL) and the warm solution was filtered to remove a small amount of insoluble material. The filtrate was allowed to stir with cooling to room temperature and then to -15° C. The solids were collected by filtration, washing with cold t-butyl methyl ether and heptane, and then dried under high vacuum to yield (1R)-1-(4-pyridinyl)ethanol as a dark beige solid (62 g, 52.9percent yield). This solid material was 96percent ee based on chiral HPLC (HPLC conditions: AS-H column, 5percent MeOH/CO2, 40° C., 140 bar, 2 mL/min). The filtrate was combined with the insoluble solid from the crystallization and concentrated in vacuo to yield additional (1R)-1-(4-pyridinyl)ethanol as a dark oil (37.5 g, 32percent yield). This oily material was 78percent ee based on chiral HPLC (see HPLC conditions above). 1H NMR (400 MHz, DMSO-d6): δ 8.47-8.43 (m, 2H), 7.32-7.28 (m, 2H), 5.37 (d, 1H, J=4.4 Hz), 4.72-4.64 (m, 1H), 1.44 (d, 3H, J=6.6 Hz).
50 % ee With hydrogen; lithium hydroxide; 9-amino-9-deoxyepicinchonine In methanol at 25℃; for 20 h; Autoclave General procedure: Definite quantities of catalyst, chiral diamine, base, solvent, and heteroaromatic methyl ketones were placed into a 60mL stainless steel autoclave equipped with a magnetic stirrer bar. The autoclave was purged with hydrogen three times and the hydrogen pressure was increased to the desired level. The mixture was then stirred at room temperature for a suitable time. At the end of the reaction, the reactor was decompressed. Finally, the products were separated by centrifugation and analyzed by a GC instrument with an FID detector and β-DEX120 capillary column. The ee value was calculated from the equation: ee (percent)=100×(S−R)/(S+R).
Reference: [1] Chemische Berichte, 1989, vol. 122, p. 1375 - 1376
[2] Tetrahedron Letters, 1993, vol. 34, # 5, p. 785 - 788
[3] Journal of the Chemical Society, Chemical Communications, 1987, p. 801 - 803
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 10, p. 1295 - 1298
[5] Heterocycles, 1996, vol. 42, # 2, p. 831 - 836
[6] Tetrahedron Letters, 1993, vol. 34, # 26, p. 4145 - 4148
[7] Phytochemistry, 1998, vol. 49, # 6, p. 1627 - 1629
[8] Phytochemistry, 1998, vol. 49, # 6, p. 1627 - 1629
[9] Tetrahedron Letters, 2000, vol. 41, # 48, p. 9277 - 9280
[10] Chemistry - A European Journal, 2001, vol. 7, # 7, p. 1431 - 1436
[11] Advanced Synthesis and Catalysis, 2004, vol. 346, # 1, p. 57 - 62
[12] Journal of Organic Chemistry, 2004, vol. 69, # 15, p. 4885 - 4890
[13] Journal of Organic Chemistry, 2005, vol. 70, # 20, p. 8079 - 8087
[14] Tetrahedron Asymmetry, 2006, vol. 17, # 12, p. 1769 - 1774
[15] Tetrahedron Letters, 2006, vol. 47, # 48, p. 8515 - 8518
[16] Journal of Organic Chemistry, 2006, vol. 71, # 18, p. 7035 - 7044
[17] Tetrahedron, 2007, vol. 63, # 19, p. 4061 - 4066
[18] Organic Letters, 2002, vol. 4, # 23, p. 4045 - 4048
[19] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 19, p. 3205 - 3211
[20] Tetrahedron Letters, 2007, vol. 48, # 25, p. 4335 - 4338
[21] Chemical Communications, 2006, # 30, p. 3232 - 3234
[22] Patent: US2008/200672, 2008, A1, . Location in patent: Page/Page column 2
[23] Monatshefte fur Chemie, 2008, vol. 139, # 7, p. 793 - 798
[24] Synthetic Communications, 2009, vol. 39, # 15, p. 2737 - 2746
[25] Synthesis, 2009, # 14, p. 2413 - 2417
[26] Synthesis, 2009, # 14, p. 2413 - 2417
[27] Chemistry - A European Journal, 2009, vol. 15, # 24, p. 5888 - 5891
[28] Chemistry - A European Journal, 2009, vol. 15, # 24, p. 5888 - 5891
[29] Patent: US2010/29650, 2010, A1, . Location in patent: Page/Page column 75
[30] Chemical Communications, 2010, vol. 46, # 25, p. 4475 - 4477
[31] Synthetic Communications, 2011, vol. 41, # 1, p. 73 - 84
[32] Advanced Synthesis and Catalysis, 2011, vol. 353, # 8, p. 1213 - 1217
[33] Advanced Synthesis and Catalysis, 2011, vol. 353, # 9, p. 1457 - 1462
[34] Chemistry - An Asian Journal, 2010, vol. 5, # 7, p. 1687 - 1691
[35] Tetrahedron Asymmetry, 2014, vol. 25, # 10-11, p. 821 - 824
[36] Advanced Synthesis and Catalysis, 2014, vol. 356, # 10, p. 2293 - 2302
[37] Angewandte Chemie - International Edition, 2014, vol. 54, # 17, p. 5171 - 5174[38] Angew. Chem., 2014, vol. 127, # 17, p. 5260 - 5263,4
[39] ACS Catalysis, 2018, vol. 8, # 9, p. 8336 - 8345
  • 4
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Reference: [1] Heterocycles, 1987, vol. 26, # 12, p. 3051 - 3054
[2] Tetrahedron: Asymmetry, 1992, vol. 3, # 7, p. 827 - 830
[3] Journal of the Chemical Society, Chemical Communications, 1988, p. 598 - 600
  • 5
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Reference: [1] Tetrahedron: Asymmetry, 1994, vol. 5, # 7, p. 1363 - 1366
[2] Bioorganic Chemistry, 1999, vol. 27, # 1, p. 3 - 19
[3] Journal of the American Chemical Society, 2005, vol. 127, # 35, p. 12228 - 12229
[4] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 24, p. 4439 - 4444
  • 6
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  • [ 27854-88-2 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 35, p. 12228 - 12229
  • 7
  • [ 23389-75-5 ]
  • [ 54519-07-2 ]
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Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 35, p. 12228 - 12229
  • 8
  • [ 23389-75-5 ]
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Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 35, p. 12228 - 12229
  • 9
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1988, p. 598 - 600
[2] Heterocycles, 1987, vol. 26, # 12, p. 3051 - 3054
[3] Tetrahedron: Asymmetry, 1992, vol. 3, # 7, p. 827 - 830
[4] Tetrahedron: Asymmetry, 1992, vol. 3, # 7, p. 827 - 830
  • 10
  • [ 2555-02-4 ]
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1988, p. 598 - 600
  • 11
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  • [ 27854-88-2 ]
  • [ 143840-01-1 ]
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 36, p. 9228 - 9237
[2] Green Chemistry, 2017, vol. 19, # 21, p. 5250 - 5256
[3] Bioorganic Chemistry, 2005, vol. 33, # 4, p. 325 - 337
[4] RSC Advances, 2015, vol. 5, # 6, p. 4592 - 4598
  • 12
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Reference: [1] ChemCatChem, 2016, vol. 8, # 10, p. 1769 - 1772
  • 13
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Reference: [1] Chirality, 2017, vol. 29, # 12, p. 811 - 823
  • 14
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Reference: [1] Chirality, 2017, vol. 29, # 12, p. 811 - 823
  • 15
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Reference: [1] Chirality, 2017, vol. 29, # 12, p. 811 - 823
  • 16
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 24, p. 4439 - 4444
  • 17
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Reference: [1] Chemische Berichte, 1989, vol. 122, p. 1375 - 1376
[2] Chemische Berichte, 1989, vol. 122, p. 1375 - 1376
[3] Chemische Berichte, 1989, vol. 122, p. 1375 - 1376
  • 18
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Reference: [1] Chirality, 2017, vol. 29, # 12, p. 811 - 823
  • 19
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Reference: [1] Tetrahedron: Asymmetry, 1992, vol. 3, # 7, p. 827 - 830
  • 20
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Reference: [1] Tetrahedron: Asymmetry, 1992, vol. 3, # 7, p. 827 - 830
  • 21
  • [ 54656-96-1 ]
  • [ 88549-54-6 ]
  • [ 3508-94-9 ]
  • [ 88549-66-0 ]
  • [ 88549-66-0 ]
Reference: [1] Angewandte Chemie, 1984, vol. 96, # 2, p. 166 - 167
[2] Angewandte Chemie, 1984, vol. 96, # 2, p. 166 - 167
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  • [ 143840-01-1 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 24, p. 8817 - 8825
  • 23
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  • [ 27854-88-2 ]
YieldReaction ConditionsOperation in experiment
78 % ee With formic acid; triethylamine In tert-butyl methyl etherInert atmosphere Triethylamine (315 mL, 2.26 mol) was added dropwise to formic acid (150 mL, 3.91 mol) with overhead stirring while maintaining the internal temperature below 60° C. with ice-bath cooling. Neat 4-acetylpyridine (100 mL, 0.904 mol) was then added rapidly while maintaining the temperature below 50° C. Following this addition, the reaction was allowed to cool to 28° C. and the chiral ruthenium catalyst [N-[(1R,2R)-2-(amino-N)-1,2-diphenylethyl]-2,4,6-trimethylbenzenesulfonamidato-N]chloro[(1,2,3,4,5,6-n)-1-methyl-4-(1-methylethyl)benzene]ruthenium (CAS No.177552-91-9; for catalyst preparation, see: Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R.; J. Am. Chem. Soc. 1996, 118, 4916-4917) (3 g, 4.46 mmol) was added. The mixture was stirred under house vacuum for 4 h and then overnight under an atmosphere of nitrogen. The reaction mixture was added dropwise to a stirred solution of 10percent Na2CO3 (4 L) and then extracted with EtOAc (3.x.1 L). The combined EtOAc layers were washed once with brine (1 L), treated with MgSO4 and Darco G-60 decolorizing charcoal and filtered through a 100 g plug of silica gel washing with 10percent MeOH/EtOAc (1 L). The filtrate was concentrated to provide a dark oil that crystallized upon standing. The solid was dissolved in warm t-butyl methyl ether (250 mL) and the warm solution was filtered to remove a small amount of insoluble material. The filtrate was allowed to stir with cooling to room temperature and then to -15° C. The solids were collected by filtration, washing with cold t-butyl methyl ether and heptane, and then dried under high vacuum to yield (1R)-1-(4-pyridinyl)ethanol as a dark beige solid (62 g, 52.9percent yield). This solid material was 96percent ee based on chiral HPLC (HPLC conditions: AS-H column, 5percent MeOH/CO2, 40° C., 140 bar, 2 mL/min). The filtrate was combined with the insoluble solid from the crystallization and concentrated in vacuo to yield additional (1R)-1-(4-pyridinyl)ethanol as a dark oil (37.5 g, 32percent yield). This oily material was 78percent ee based on chiral HPLC (see HPLC conditions above). 1H NMR (400 MHz, DMSO-d6): δ 8.47-8.43 (m, 2H), 7.32-7.28 (m, 2H), 5.37 (d, 1H, J=4.4 Hz), 4.72-4.64 (m, 1H), 1.44 (d, 3H, J=6.6 Hz).
50 % ee With hydrogen; lithium hydroxide; 9-amino-9-deoxyepicinchonine In methanol at 25℃; for 20 h; Autoclave General procedure: Definite quantities of catalyst, chiral diamine, base, solvent, and heteroaromatic methyl ketones were placed into a 60mL stainless steel autoclave equipped with a magnetic stirrer bar. The autoclave was purged with hydrogen three times and the hydrogen pressure was increased to the desired level. The mixture was then stirred at room temperature for a suitable time. At the end of the reaction, the reactor was decompressed. Finally, the products were separated by centrifugation and analyzed by a GC instrument with an FID detector and β-DEX120 capillary column. The ee value was calculated from the equation: ee (percent)=100×(S−R)/(S+R).
Reference: [1] Chemische Berichte, 1989, vol. 122, p. 1375 - 1376
[2] Tetrahedron Letters, 1993, vol. 34, # 5, p. 785 - 788
[3] Journal of the Chemical Society, Chemical Communications, 1987, p. 801 - 803
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 10, p. 1295 - 1298
[5] Heterocycles, 1996, vol. 42, # 2, p. 831 - 836
[6] Tetrahedron Letters, 1993, vol. 34, # 26, p. 4145 - 4148
[7] Phytochemistry, 1998, vol. 49, # 6, p. 1627 - 1629
[8] Phytochemistry, 1998, vol. 49, # 6, p. 1627 - 1629
[9] Tetrahedron Letters, 2000, vol. 41, # 48, p. 9277 - 9280
[10] Chemistry - A European Journal, 2001, vol. 7, # 7, p. 1431 - 1436
[11] Advanced Synthesis and Catalysis, 2004, vol. 346, # 1, p. 57 - 62
[12] Journal of Organic Chemistry, 2004, vol. 69, # 15, p. 4885 - 4890
[13] Journal of Organic Chemistry, 2005, vol. 70, # 20, p. 8079 - 8087
[14] Tetrahedron Asymmetry, 2006, vol. 17, # 12, p. 1769 - 1774
[15] Tetrahedron Letters, 2006, vol. 47, # 48, p. 8515 - 8518
[16] Journal of Organic Chemistry, 2006, vol. 71, # 18, p. 7035 - 7044
[17] Tetrahedron, 2007, vol. 63, # 19, p. 4061 - 4066
[18] Organic Letters, 2002, vol. 4, # 23, p. 4045 - 4048
[19] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 19, p. 3205 - 3211
[20] Tetrahedron Letters, 2007, vol. 48, # 25, p. 4335 - 4338
[21] Chemical Communications, 2006, # 30, p. 3232 - 3234
[22] Patent: US2008/200672, 2008, A1, . Location in patent: Page/Page column 2
[23] Monatshefte fur Chemie, 2008, vol. 139, # 7, p. 793 - 798
[24] Synthetic Communications, 2009, vol. 39, # 15, p. 2737 - 2746
[25] Synthesis, 2009, # 14, p. 2413 - 2417
[26] Synthesis, 2009, # 14, p. 2413 - 2417
[27] Chemistry - A European Journal, 2009, vol. 15, # 24, p. 5888 - 5891
[28] Chemistry - A European Journal, 2009, vol. 15, # 24, p. 5888 - 5891
[29] Patent: US2010/29650, 2010, A1, . Location in patent: Page/Page column 75
[30] Chemical Communications, 2010, vol. 46, # 25, p. 4475 - 4477
[31] Synthetic Communications, 2011, vol. 41, # 1, p. 73 - 84
[32] Advanced Synthesis and Catalysis, 2011, vol. 353, # 8, p. 1213 - 1217
[33] Advanced Synthesis and Catalysis, 2011, vol. 353, # 9, p. 1457 - 1462
[34] Chemistry - An Asian Journal, 2010, vol. 5, # 7, p. 1687 - 1691
[35] Tetrahedron Asymmetry, 2014, vol. 25, # 10-11, p. 821 - 824
[36] Advanced Synthesis and Catalysis, 2014, vol. 356, # 10, p. 2293 - 2302
[37] Angewandte Chemie - International Edition, 2014, vol. 54, # 17, p. 5171 - 5174[38] Angew. Chem., 2014, vol. 127, # 17, p. 5260 - 5263,4
[39] ACS Catalysis, 2018, vol. 8, # 9, p. 8336 - 8345
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YieldReaction ConditionsOperation in experiment
80 % ee at 35℃; for 0.333333 h; Resolution of racemate; Enzymatic reaction A mixture of (±)-1g (50.3mg, 0.41mmol), vinyl acetate (53.8mg, 0.61mmol), and PYET-PS (5.1mg) in i-Pr2O (2.0ml) was stirred at 35°C for 20min. The reaction was quenched by the addition of 1.0ml of ethyl acetate and the enzyme was removed by filtration through a glass sintered filter with a Celite pad, then silica gel TLC (ethyl acetate) gave (R)-2g and (S)-1g. (R)-2g: 23.9mg, 0.050mmol, Y=34percent, >99percent ee. (S)-1g: 28.9mg, 0.23mmol, Y=56percent, 80percent ee. Conv. 45percent, E value>200, Rate: 1274mMh−1 mg enzyme−1
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 36, p. 9228 - 9237
[2] Green Chemistry, 2017, vol. 19, # 21, p. 5250 - 5256
[3] Tetrahedron, 2019, vol. 75, # 4, p. 441 - 447
[4] Bioorganic Chemistry, 2005, vol. 33, # 4, p. 325 - 337
[5] RSC Advances, 2015, vol. 5, # 6, p. 4592 - 4598
  • 25
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Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 35, p. 12228 - 12229
  • 26
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Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 35, p. 12228 - 12229
  • 27
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  • [ 27854-88-2 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 35, p. 12228 - 12229
  • 28
  • [ 54656-96-1 ]
  • [ 27854-88-2 ]
Reference: [1] Phytochemistry, 1998, vol. 49, # 6, p. 1627 - 1629
  • 29
  • [ 2555-02-4 ]
  • [ 54656-96-1 ]
  • [ 27854-88-2 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1988, p. 598 - 600
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  • [ 330460-83-8 ]
  • [ 54656-96-1 ]
  • [ 27854-88-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 24, p. 4439 - 4444
  • 31
  • [ 2555-02-4 ]
  • [ 54656-96-1 ]
  • [ 66842-22-6 ]
  • [ 27854-88-2 ]
Reference: [1] Chemische Berichte, 1989, vol. 122, p. 1375 - 1376
[2] Chemische Berichte, 1989, vol. 122, p. 1375 - 1376
[3] Chemische Berichte, 1989, vol. 122, p. 1375 - 1376
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