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[ CAS No. 863377-22-4 ] {[proInfo.proName]}

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Chemical Structure| 863377-22-4
Chemical Structure| 863377-22-4
Structure of 863377-22-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 863377-22-4 ]

CAS No. :863377-22-4 MDL No. :MFCD03412095
Formula : C10H14BNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :OHGOMHOEZUWGOH-UHFFFAOYSA-N
M.W : 207.03 Pubchem ID :4192661
Synonyms :

Calculated chemistry of [ 863377-22-4 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 61.99
TPSA : 52.93 Ų

Pharmacokinetics

GI absorption : High
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) : -7.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.58
Log Po/w (WLOGP) : -1.18
Log Po/w (MLOGP) : -0.29
Log Po/w (SILICOS-IT) : -0.68
Consensus Log Po/w : -0.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.65
Solubility : 4.6 mg/ml ; 0.0222 mol/l
Class : Very soluble
Log S (Ali) : -1.26
Solubility : 11.3 mg/ml ; 0.0544 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.48
Solubility : 6.86 mg/ml ; 0.0331 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.02

Safety of [ 863377-22-4 ]

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 [ 863377-22-4 ]

* 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 [ 863377-22-4 ]
  • Downstream synthetic route of [ 863377-22-4 ]

[ 863377-22-4 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 5419-55-6 ]
  • [ 197846-82-5 ]
  • [ 863377-22-4 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 2 h;
Stage #2: at 20℃; Cooling with acetone-dry ice
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane
To a stirred mixture of 4-(3-bromophenyl) morpholine (16.5g, 0.068mol) in dry THF(300mL) was added n-BuLi (98.1mL, 0.102mol, 1.6M solution in n-hexane) dropwise at -70°C to -78°C. The mixture was stirred at the same temperature for 2h. To this reaction mixture was added tri-isopropyl borate (30.5mL, 0.150mol) dropwise whilst maintaining the temperature. The dry ice-acetone bath was removed and the mixture was allowed to warm to room temperature and stirred at room temperature overnight.The mixture was poured into a saturated solution of ammonium chloride and water added and the reaction mixture was extracted with ethyl acetate. The organic phase was dried (MgS04) and the solvent removed under reduced pressure and below 40°C.The residue was triturated with n-hexane and diethyl ether to afford 3-morpholin-4- ylphenylboronic acid (12g, 85percent) as an off-white solid.Mass: (ES+) 208 (M+H)+ NMR: 5H (d6-DMSO) 3.05 (4H, m), 3.72 (4H, m), 6.95 (1H, d), 7.18 (1H, t), 7.21 (1H, d), 7.38 (1H, br s) and 7.94 (2H, s).
85%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 70℃;
Stage #2: at -78 - 20℃;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane
To a stirred mixture of 4-(3-bromophenyl)morpholine (16.5g, 0.068mol) in dry THF (300mL) was added n-butyl lithium (98.1mL, 0.102mol, 1.6M solution in n-hexane) dropwise at -70°C to -78°C. The mixture was stirred at same temperature for 2h. To this reaction mixture was added tri-isopropyl borate (30.5mL, 0.150mol) dropwise whilst maintaining the temperature at -70°C to -78°C. The dry ice-acetone bath was removed and the mixture was allowed to warm to room temperature and stirred at room temperature overnight. The mixture was poured into a saturated solution of ammonium chloride and water added and the reaction mixture was extracted with ethyl acetate. The organic phase was dried (MgS04) and the solvent removed under reduced pressure. The residue was triturated with n-hexane and diethyl ether to afford 3-morpholin-4-yl-phenylboronic acid (12g, 85percent) as an off white solid.Mass: (ES+) 208 (M+H)+ NMR: 5H (^-DMSO) 3.05 (4H, m), 3.72 (4H, m), 6.95 (1H, d), 7.18 (1H, t), 7.21 (1H, d), 7.38 (1H, br s) and 7.94 (2H, s).
Reference: [1] Patent: WO2011/144577, 2011, A1, . Location in patent: Page/Page column 26
[2] Patent: WO2011/144578, 2011, A1, . Location in patent: Page/Page column 28; 29
  • 2
  • [ 108-36-1 ]
  • [ 863377-22-4 ]
Reference: [1] Patent: WO2011/144577, 2011, A1,
[2] Patent: WO2011/144578, 2011, A1,
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