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[ CAS No. 59830-60-3 ] {[proInfo.proName]}

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Chemical Structure| 59830-60-3
Chemical Structure| 59830-60-3
Structure of 59830-60-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 59830-60-3 ]

CAS No. :59830-60-3 MDL No. :MFCD00798796
Formula : C17H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :HZDPJHOWPIVWMR-INIZCTEOSA-N
M.W : 283.32 Pubchem ID :7021150
Synonyms :

Calculated chemistry of [ 59830-60-3 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.18
Num. rotatable bonds : 8
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 79.8
TPSA : 55.4 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 2.96
Log Po/w (WLOGP) : 2.57
Log Po/w (MLOGP) : 2.49
Log Po/w (SILICOS-IT) : 3.14
Consensus Log Po/w : 2.74

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.36
Solubility : 0.125 mg/ml ; 0.00044 mol/l
Class : Soluble
Log S (Ali) : -3.79
Solubility : 0.0464 mg/ml ; 0.000164 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.46
Solubility : 0.000987 mg/ml ; 0.00000348 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.77

Safety of [ 59830-60-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 59830-60-3 ]

* 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 [ 59830-60-3 ]
  • Downstream synthetic route of [ 59830-60-3 ]

[ 59830-60-3 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 114744-85-3 ]
  • [ 59830-60-3 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran
Lithium aluminum hydride (0.95 mL of a 1.0 M solution in THF, 0.95 mmoles) was added to a room temperature solution of [(S)-1-(Methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester (0.30 g, 0.86 mmoles) in THF (10 mL). The resulting mixture was stirred at room temperature for 2 h, then was quenched by dilution with EtOAc (200 mL), and washed with 1percent aqueous HCl (200 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was repeatedly diluted with CH3CN (2.x.200 mL) and concentrated in vacuo to give 0.24 g (approximately quantitative yield) of ((S)-1-Benzyl-2-oxo-ethyl)-carbamic acid benzyl ester as a colorless oil, which was carried on without further purification: ES+LC/MS m/e 284 (M+H), RT=4.75 min.
Reference: [1] Patent: US2008/139556, 2008, A1, . Location in patent: Page/Page column 18; 46
[2] Journal of Organic Chemistry, 2016, vol. 81, # 4, p. 1416 - 1424
[3] Tetrahedron Letters, 2000, vol. 41, # 32, p. 6131 - 6135
[4] Tetrahedron, 1996, vol. 52, # 1, p. 305 - 318
[5] Tetrahedron Letters, 1998, vol. 39, # 11, p. 1341 - 1344
[6] Tetrahedron Letters, 1988, vol. 29, # 30, p. 3687 - 3690
[7] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 11, p. 1159 - 1162
[8] Patent: WO2006/12256, 2006, A2, . Location in patent: Page/Page column 87
[9] Patent: WO2015/95227, 2015, A2, . Location in patent: Page/Page column 218
[10] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 989 - 1000
  • 2
  • [ 1161-13-3 ]
  • [ 59830-60-3 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 10, p. 1347 - 1350
[2] Tetrahedron, 2007, vol. 63, # 28, p. 6577 - 6586
[3] Journal of Organic Chemistry, 1976, vol. 41, # 20, p. 3317 - 3321
[4] Synlett, 2005, # 18, p. 2802 - 2804
[5] Synlett, 2004, # 3, p. 477 - 480
[6] Synlett, 2004, # 3, p. 477 - 480
[7] Synthesis, 2002, # 8, p. 1121 - 1123
[8] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 11, p. 1159 - 1162
[9] Tetrahedron Letters, 2000, vol. 41, # 32, p. 6131 - 6135
[10] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1921 - 1924
[11] Tetrahedron Letters, 1992, vol. 33, # 30, p. 4257 - 4260
[12] Synlett, 2013, vol. 24, # 6, p. 747 - 751
[13] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 17, p. 5407 - 5413
[14] Patent: WO2015/95227, 2015, A2,
[15] Organic and Biomolecular Chemistry, 2015, vol. 13, # 42, p. 10456 - 10460
[16] Patent: US2008/139556, 2008, A1,
  • 3
  • [ 35909-92-3 ]
  • [ 59830-60-3 ]
Reference: [1] Tetrahedron Asymmetry, 2005, vol. 16, # 3, p. 739 - 743
[2] Chemical & Pharmaceutical Bulletin, 1989, vol. 37, # 10, p. 2867 - 2869
[3] Journal of the American Chemical Society, 1983, vol. 105, # 16, p. 5510 - 5512
[4] Synlett, 1999, # SPEC. ISS., p. 873 - 876
[5] Heterocycles, 2001, vol. 54, # 2, p. 581 - 584
[6] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 24, p. 2989 - 2992
[7] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1921 - 1924
[8] Patent: US6048841, 2000, A,
[9] Patent: US5587388, 1996, A,
[10] Patent: US5698706, 1997, A,
[11] Patent: EP601486, 1994, A1,
[12] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 17, p. 5407 - 5413
[13] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 18, p. 4486 - 4489
  • 4
  • [ 6372-14-1 ]
  • [ 59830-60-3 ]
YieldReaction ConditionsOperation in experiment
76% With sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine In dichloromethane; dimethyl sulfoxide at 0℃; for 0.5 h; Reference compound 7 (40 g, 140 mmol) was dissolved in dimethyl sulfoxide (160 mL) and dichloromethane (80 mL) and the mixture was ice-cooled. Thereto was added a suspension (80 mL) of N,N-diisopropylethylamine (54 g, 420 mmol) and sulfur trioxide pyridine complex (67 g, 420 mmol) in dimethyl sulfoxide. This solution was stirred under ice-cooling for 30 min. This reaction mixture was diluted with ethyl acetate, washed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from a hexane/ethyl acetate mixed solution to give Reference compound 25 (30 g, 76percent) as colorless crystals. mp 66.2-66.9°C. 1H-NMR (300 MHz, DMSO-d6)δ:2.72 (dd, 1H, J = 14.1, 10.4 Hz), 3.15 (dd, 1H, J = 14.1, 4.2 Hz), 4.2 (m, 1H), 4.96-5.05 (m, 2H), 7.19-7.39 (m, 10H), 7.76 (d, 1H, J = 7.8 Hz), 9.57 (s, 1H). Anal. Calcd for C17H17NO3: C, 72.07; H, 6.05; N, 4.94. Found: C, 71.69; H, 6.30; N, 4.76.
1.1 g With Dess-Martin periodane In dichloromethane at 0 - 20℃; Inert atmosphere Intermediate S20 (0.250 g, 0.86 mmol) and Dess-Martin periodinane (1.53 g, 3.62 mmol) in DCM (50 mL) was stirred at 0 °C and then allowed to warm room temperature. The additional amount of oxidant was added if the conversion was not complete (TLC control, light petroleum ether : EtOAc, 1:1). After completion of the reaction, it was diluted with DCM (20 mL). The reaction mixture was washed with 0.2 M Na2S2O3 solution (2 x 20 mL) then with 1 M NaHCO3 solution (2x20 mL) and brine (20 mL). The organic phase was dried over Na2SO4 and evaporated in vacuo. Crude product was purified by flash chromatography eluting with a mixture of light petroleum ether : EtOAc, 1:1 to provide 31a (0.10 g, 40percent) as colourless solid.
Reference: [1] Advanced Synthesis and Catalysis, 2003, vol. 345, # 5, p. 635 - 642
[2] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 17, p. 2475 - 2482
[3] Tetrahedron Letters, 1992, vol. 33, # 35, p. 5029 - 5032
[4] Tetrahedron Letters, 1992, vol. 33, # 35, p. 5029 - 5032
[5] Organic Process Research and Development, 2003, vol. 7, # 6, p. 839 - 845
[6] Heterocycles, 1987, vol. 26, # 11, p. 2805 - 2809
[7] Collection of Czechoslovak Chemical Communications, 1995, vol. 60, # 4, p. 693 - 696
[8] Journal of the American Chemical Society, 1999, vol. 121, # 6, p. 1145 - 1155
[9] Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7907 - 7909
[10] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1046 - 1052
[11] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1921 - 1924
[12] Synlett, 2003, # 14, p. 2249 - 2251
[13] European Journal of Organic Chemistry, 2010, # 24, p. 4671 - 4686
[14] Journal of the American Chemical Society, 2011, vol. 133, # 17, p. 6497 - 6500
[15] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 705 - 710
[16] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 24, p. 5449 - 5460
[17] Patent: EP1491537, 2004, A1, . Location in patent: Page 17
[18] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 14, p. 3945 - 3948
[19] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 535 - 540
[20] European Journal of Organic Chemistry, 2017, vol. 2017, # 47, p. 7019 - 7025
[21] Chemistry Letters, 1987, p. 1531 - 1534
[22] Journal of the Chemical Society, Chemical Communications, 1993, # 13, p. 1052 - 1053
[23] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 2, p. 364 - 370
[24] Tetrahedron Letters, 1992, vol. 33, # 30, p. 4257 - 4260
[25] Journal of Organic Chemistry, 1992, vol. 57, # 21, p. 5692 - 5700
[26] Journal of Organic Chemistry, 1992, vol. 57, # 1, p. 28 - 32
[27] Journal of the American Chemical Society, 1994, vol. 116, # 4, p. 1316 - 1323
[28] Bulletin of the Polish Academy of Sciences, Chemistry, 1994, vol. 42, # 1, p. 117 - 130
[29] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 24, p. 2989 - 2992
[30] European Journal of Organic Chemistry, 1999, # 7, p. 1551 - 1560
[31] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 12, p. 2953 - 2959
[32] Heterocycles, 2001, vol. 54, # 2, p. 581 - 584
[33] Synlett, 2005, # 18, p. 2802 - 2804
[34] Organic Letters, 2001, vol. 3, # 19, p. 3041 - 3043
[35] Patent: US5362912, 1994, A,
[36] Tetrahedron Letters, 2009, vol. 50, # 5, p. 552 - 554
[37] European Journal of Organic Chemistry, 2008, # 27, p. 4655 - 4664
[38] Patent: WO2008/97673, 2008, A1, . Location in patent: Page/Page column 21-22
[39] Patent: WO2008/97676, 2008, A1, . Location in patent: Page/Page column 51
[40] Chemistry - A European Journal, 2009, vol. 15, # 30, p. 7310 - 7328
[41] Monatshefte fur Chemie, 2010, vol. 141, # 2, p. 177 - 198
[42] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 3992 - 3996
[43] Patent: US2012/22251, 2012, A1, . Location in patent: Page/Page column 40
[44] Synlett, 2013, vol. 24, # 6, p. 747 - 751
[45] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 18, p. 4486 - 4489
[46] Patent: US2016/222060, 2016, A1, . Location in patent: Paragraph 0503; 0504; 0505
[47] Journal of Medicinal Chemistry, 2017, vol. 60, # 16, p. 7123 - 7138
[48] European Journal of Organic Chemistry, 2018, vol. 2018, # 27, p. 3844 - 3852
  • 5
  • [ 60718-38-9 ]
  • [ 59830-60-3 ]
Reference: [1] Synlett, 2004, # 3, p. 477 - 480
[2] Synthesis, 2002, # 8, p. 1121 - 1123
  • 6
  • [ 684212-67-7 ]
  • [ 59830-60-3 ]
Reference: [1] ACS Catalysis, 2014, vol. 4, # 6, p. 2070 - 2074
[2] Synlett, 2004, # 3, p. 477 - 480
  • 7
  • [ 3182-95-4 ]
  • [ 59830-60-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 24, p. 5449 - 5460
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 705 - 710
[3] Heterocycles, 1987, vol. 26, # 11, p. 2805 - 2809
[4] Journal of the American Chemical Society, 1994, vol. 116, # 4, p. 1316 - 1323
[5] Journal of Organic Chemistry, 1992, vol. 57, # 1, p. 28 - 32
[6] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 535 - 540
[7] European Journal of Organic Chemistry, 2018, vol. 2018, # 27, p. 3844 - 3852
  • 8
  • [ 501-53-1 ]
  • [ 59830-60-3 ]
Reference: [1] Heterocycles, 2001, vol. 54, # 2, p. 581 - 584
[2] Heterocycles, 1987, vol. 26, # 11, p. 2805 - 2809
[3] Journal of the American Chemical Society, 1994, vol. 116, # 4, p. 1316 - 1323
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 535 - 540
  • 9
  • [ 25613-60-9 ]
  • [ 59830-60-3 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 48, p. 9031 - 9034
  • 10
  • [ 133010-22-7 ]
  • [ 59830-60-3 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 40, p. 7281 - 7284
  • 11
  • [ 6372-14-1 ]
  • [ 77-92-9 ]
  • [ 59830-60-3 ]
Reference: [1] Patent: US5362912, 1994, A,
  • 12
  • [ 79-37-8 ]
  • [ 3182-95-4 ]
  • [ 59830-60-3 ]
Reference: [1] Patent: US5362912, 1994, A,
  • 13
  • [ 79-37-8 ]
  • [ 6372-14-1 ]
  • [ 59830-60-3 ]
Reference: [1] Patent: US5559158, 1996, A,
  • 14
  • [ 79-37-8 ]
  • [ 6372-14-1 ]
  • [ 59830-60-3 ]
Reference: [1] Patent: US5461067, 1995, A,
  • 15
  • [ 52641-32-4 ]
  • [ 59830-60-3 ]
Reference: [1] ACS Catalysis, 2014, vol. 4, # 6, p. 2070 - 2074
  • 16
  • [ 28709-70-8 ]
  • [ 59830-60-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1975, vol. 23, # 12, p. 3081 - 3087
[2] Tetrahedron Letters, 1990, vol. 31, # 50, p. 7359 - 7362
  • 17
  • [ 62750-39-4 ]
  • [ 59830-60-3 ]
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 42, p. 10456 - 10460
  • 18
  • [ 41518-17-6 ]
  • [ 59830-60-3 ]
Reference: [1] Synthesis, 2002, # 8, p. 1121 - 1123
  • 19
  • [ 3397-32-8 ]
  • [ 59830-60-3 ]
Reference: [1] Synlett, 2005, # 18, p. 2802 - 2804
[2] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 12, p. 2953 - 2959
  • 20
  • [ 13139-17-8 ]
  • [ 59830-60-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 24, p. 5449 - 5460
  • 21
  • [ 63-91-2 ]
  • [ 59830-60-3 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 27, p. 3844 - 3852
  • 22
  • [ 3182-93-2 ]
  • [ 59830-60-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1975, vol. 23, # 12, p. 3081 - 3087
  • 23
  • [ 51987-73-6 ]
  • [ 59830-60-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 18, p. 4486 - 4489
  • 24
  • [ 2577-90-4 ]
  • [ 59830-60-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 18, p. 4486 - 4489
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