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[ CAS No. 90481-32-6 ] {[proInfo.proName]}

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Chemical Structure| 90481-32-6
Chemical Structure| 90481-32-6
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Product Details of [ 90481-32-6 ]

CAS No. :90481-32-6 MDL No. :MFCD08686737
Formula : C4H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :JCZPOYAMKJFOLA-IMJSIDKUSA-N
M.W : 103.12 Pubchem ID :146198
Synonyms :

Calculated chemistry of [ 90481-32-6 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 28.27
TPSA : 52.49 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.9
Log Po/w (XLOGP3) : -1.67
Log Po/w (WLOGP) : -2.07
Log Po/w (MLOGP) : -1.45
Log Po/w (SILICOS-IT) : -0.43
Consensus Log Po/w : -0.94

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.57
Solubility : 386.0 mg/ml ; 3.74 mol/l
Class : Highly soluble
Log S (Ali) : 1.08
Solubility : 1240.0 mg/ml ; 12.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.64
Solubility : 454.0 mg/ml ; 4.41 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.76

Safety of [ 90481-32-6 ]

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 [ 90481-32-6 ]

* 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 [ 90481-32-6 ]
  • Downstream synthetic route of [ 90481-32-6 ]

[ 90481-32-6 ] Synthesis Path-Upstream   1~3

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  • [ 90365-74-5 ]
  • [ 90481-32-6 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With hydrogen; acetic acid In ethanol at 20℃; for 7 h;
Stage #2: With hydrogenchloride In 1,4-dioxane
To a solution of (3S,4S)-1-benzylpynolidne-3,4-diol (522 mg) in ethanol (15 mL) were added 10percent palladium-carbon (100 mg) and acetic acid (10 mL), and the mixture was reacted under pressurized hydrogen (40psi) at room temperature for 7 hours in Parr hydrogenation apparatus. The reaction solution was filtered through Celite, and the filtrate was concentrated under reduced pressure. To the resulting residue was added 4N hydrochloric acid-dioxane solution, and then the mixture was concentrated under reduced pressure to give the titled compound (373 mg) as a yellow solid (yield 99percent). MS(APCI)m/z; 104[M+H]+.
90.9% With palladium 10% on activated carbon; hydrogen In ethanol; water at 20℃; for 48 h; Intermediate ((3S, 4S) -5) (77.3g, 0.4mol) was dissolved in 80percent aqueous ethanol (2.4L) was added 10percent Pd / C (7.0g), at room temperature through hydrogen (0.07MPa) reaction 2d. The catalyst was removed by filtration and the filtrate concentrated under reduced pressure, the residue was treated with absolute ethanol (2 × 250mL) with traces of water addition to give a yellow oil of Intermediate ((3S, 4S) -6) 37.5g, yield 90.9percent.
90.9% With palladium 10% on activated carbon; hydrogen In ethanol; water at 20℃; for 48 h; Intermediate ((3S,4S)-5) (77.3 g, 0.4 mol) was dissolved in an aqueous solution of ethanol (80percent), to which10percent Pd/C (7.0 g) was added. Hydrogen (0.07 MPa) was supplied, and the reaction was kept for 2 days at room temperature.The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. Anhydrous ethanol(23250 mL) was used to remove the trace amount of water from the residue to obtain intermediate ((3S,4S)-6) as ayellow oil (37.5 g, yield: 90.9percent).MASS (ESI+) m/z = 104 (M+H)+.1 H NMR (400 MHz, DSO-d6): 2.60 (m, 2H), 3.02 (m, 2H), 3.83 (m, 2H), 4.81 (br s, 3H).
90.9% With palladium 10% on activated carbon; hydrogen In ethanol; water at 20℃; for 48 h; The intermediate ((3S, 4S)-5) (77.3 g, 0.4 mol) Soluble in 80percent aqueous ethanol solution (2.4L),Add 10percent Pd/C (7.0g),The reaction was carried out at room temperature with hydrogen (0.07 MPa) for 2 d.The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure.The residue was stripped of water with anhydrous ethanol (2×250 mL) to give a yellow oily intermediate ((3S, 4S)-6) 37.5 g, yield: 90.9percent.
83% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 24 h; General procedure: 10 percent Pd/C (1.50 g) was added to solution of 3a (7.50 g, 38.86 mmol) in ethanol (40 mL) under argon atmosphere, hydrogenated under 100 psi at room temperature for 24 h. The reaction mixture was filtered through celite pad, filtrate was evaporated in vacuo to get crude. The crude product was washed with n-pentane-diethyl ether mixture (1:1) (20 mL), decanted the organic layer and dried in vacuo yielding 3.28 g (82.0 percent) of light brown solid of compound 4a.

Reference: [1] Synthetic Communications, 2008, vol. 38, # 14, p. 2374 - 2384
[2] Patent: EP2390254, 2011, A1, . Location in patent: Page/Page column 86
[3] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 16, p. 2385 - 2390
[4] Angewandte Chemie, 1984, vol. 96, # 6, p. 425 - 426
[5] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 12, p. 3965 - 3973
[6] Tetrahedron, 2007, vol. 63, # 5, p. 1243 - 1253
[7] Journal of Carbohydrate Chemistry, 2000, vol. 19, # 4-5, p. 585 - 601
[8] Patent: CN105693520, 2016, A, . Location in patent: Paragraph 0154; 0155; 0156; 0157; 0158; 0159
[9] Patent: EP3067351, 2016, A1, . Location in patent: Paragraph 0073; 0074
[10] Patent: CN108658947, 2018, A, . Location in patent: Paragraph 0093; 0118; 0130-0132
[11] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2818 - 2823
[12] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1265 - 1268
[13] Synthesis, 2006, # 2, p. 247 - 256
[14] Patent: US2004/19065, 2004, A1, . Location in patent: Page/Page column 22
[15] Synthesis, 2010, # 5, p. 791 - 796
[16] Chemical Research in Toxicology, 2010, vol. 23, # 1, p. 118 - 133
[17] Patent: US2012/295874, 2012, A1, . Location in patent: Page/Page column 170
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Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 7, p. 1911 - 1917
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  • [ 90481-32-6 ]
  • [ 501-53-1 ]
  • [ 596793-30-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1265 - 1268
[2] Patent: US2004/19065, 2004, A1, . Location in patent: Page/Page column 22
[3] Patent: US2012/295874, 2012, A1, . Location in patent: Page/Page column 170
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