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[ CAS No. 120157-96-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 120157-96-2
Chemical Structure| 120157-96-2
Chemical Structure| 120157-96-2
Structure of 120157-96-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 120157-96-2 ]

CAS No. :120157-96-2 MDL No. :MFCD11870086
Formula : C14H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :UDPLKASYJHMKIP-UHFFFAOYSA-N
M.W : 265.31 Pubchem ID :14221817
Synonyms :

Calculated chemistry of [ 120157-96-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.43
Num. rotatable bonds : 7
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 71.24
TPSA : 64.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.21
Log Po/w (XLOGP3) : 2.28
Log Po/w (WLOGP) : 2.35
Log Po/w (MLOGP) : 2.23
Log Po/w (SILICOS-IT) : 2.08
Consensus Log Po/w : 2.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.69
Solubility : 0.538 mg/ml ; 0.00203 mol/l
Class : Soluble
Log S (Ali) : -3.27
Solubility : 0.141 mg/ml ; 0.000532 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.83
Solubility : 0.0391 mg/ml ; 0.000147 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.0

Safety of [ 120157-96-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 120157-96-2 ]

* 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 [ 120157-96-2 ]
  • Downstream synthetic route of [ 120157-96-2 ]

[ 120157-96-2 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 120157-96-2 ]
  • [ 33233-67-9 ]
Reference: [1] Patent: EP1908752, 2008, A1, . Location in patent: Page/Page column 50
  • 2
  • [ 120157-96-2 ]
  • [ 6232-11-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 5, p. 1199 - 1212
  • 3
  • [ 120157-96-2 ]
  • [ 123986-64-1 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at -40℃; for 6 h;
Stage #2: at -30℃;
Step C) Formation of N-Boc-(4-hydroxymethyl)benzylamine; To a suspension of LAH (8. 6 g, 0.226 mol) in dry THF (700 mL) was added a solution of methyl (N-Boc-4-aminomethyl)benzoate (50 g, 0. 188 mol) in THF (300 ML) AT-40°C with stirring and stirred for 6 h. The reaction mixture was quenched with an aqueous NAOH solution (10percent of 40 mL) AT-30°C. The reaction mixture was filtered, washed with THF and concentrated under vacuum to give the title compound as white solid (41 g, 91percent).
35%
Stage #1: With lithium aluminium tetrahydride In diethyl ether at -78 - 20℃; for 3.16667 h;
Stage #2: With ammonium chloride In diethyl ether; water; ethyl acetate
To a cold suspension of LiAlH4 (60 mg, 1.5 mmol) in ether (5 mL) at -78° C. was added dropwise a solution of methyl 4-(N-t-Boc-aminomethyl)benzoate (0.8 g, 3 mmol) in ether (5 mL) and the contents were allowed to warm-up to ambient temp.
After 3 h, further amount of LiAlH4 (100 mg) was added and the reaction was continued at room temp for further 10 min.
Excess LiAlH4 was destroyed with EtOAc followed by saturated ammonium chloride (1.0 mL), The solid precipitated was filtered and washed with ether.
The filtrate was evaporated to give 4-(N-t-Boc-aminomethyl)benzyl alcohol (250 mg, 35percent).
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 15, p. 3043 - 3046
[2] Tetrahedron, 2006, vol. 62, # 9, p. 1979 - 1987
[3] Patent: WO2005/12280, 2005, A1, . Location in patent: Page/Page column 52
[4] Patent: US6680311, 2004, B1, . Location in patent: Page/Page column 151
[5] Patent: EP1612204, 2006, A1, . Location in patent: Page/Page column 41
[6] Patent: EP1724263, 2006, A1, . Location in patent: Page/Page column 48
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