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[ CAS No. 63106-93-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 63106-93-4
Chemical Structure| 63106-93-4
Chemical Structure| 63106-93-4
Structure of 63106-93-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 63106-93-4 ]

CAS No. :63106-93-4 MDL No. :MFCD09833671
Formula : C11H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WZGFIZUMKYUMRN-UHFFFAOYSA-N
M.W : 174.20 Pubchem ID :11745119
Synonyms :

Calculated chemistry of [ 63106-93-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.58
TPSA : 26.3 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) : -6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 1.73
Log Po/w (WLOGP) : 1.5
Log Po/w (MLOGP) : 2.18
Log Po/w (SILICOS-IT) : 2.73
Consensus Log Po/w : 2.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.29
Solubility : 0.903 mg/ml ; 0.00518 mol/l
Class : Soluble
Log S (Ali) : -1.9
Solubility : 2.2 mg/ml ; 0.0126 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.16
Solubility : 0.12 mg/ml ; 0.00069 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.52

Safety of [ 63106-93-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 63106-93-4 ]

* 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 [ 63106-93-4 ]
  • Downstream synthetic route of [ 63106-93-4 ]

[ 63106-93-4 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 140-29-4 ]
  • [ 106-89-8 ]
  • [ 63106-93-4 ]
YieldReaction ConditionsOperation in experiment
68.1%
Stage #1: With sodium hydride In 1,3-dimethyl-2-imidazolidinone; toluene at 10 - 20℃; for 2 h;
Stage #2: at 10 - 20℃;
In a mixed solvent of toluene (26.0 kg) and N,N'-dimethyl-2-imidazolidinone (94.9 kg), 60percent sodium hydride (27.2 kg, 683 mol) was added, and phenylacetonitrile (40.2 kg, 343 mol) was subsequently added dropwise therein at 10 to 20°C.
After being stirred for 2 hours, a mixture of epichlorohydrin (31.7 kg, 343 mol) and toluene (26.0 kg) was added dropwise therein at 10 to 20 °C and then stirred.
After confirming the disappearance of the raw material, methanol (22.0 kg) and water (120.6 kg) were added therein to be subjected to washing and phase separation.
The organic layer obtained was added with 24percent aqueous solution of potassium hydroxide (159.1 kg) and tetrabutylammonium sulfate (1.1 kg) to be heated under refluxing.
The organic phase was removed by a phase separation, and then further added with toluene (69.6 kg) and 35percent hydrochloric acid (78.7 kg), followed by stirring at 60 to 70 °C for 2 hours.
After the organic phase was separated by a phase separation, the organic phase was further washed twice with 8percent aqueous sodium hydrogen carbonate solution and twice with water; and then the organic layer obtained was concentrated under a reduced pressure to obtain 40.7 kg of the titled compound in a form of light-yellow oily substance.
Yield was 68.1percent.
The obtained oily substance of 2-oxo-1-phenyl-3-oxabicyclo[3.1.0]hexane was cooled to transform to crystals.
Reference: [1] Patent: WO2005/123709, 2005, A1, . Location in patent: Page/Page column 6-7
[2] Patent: EP1767522, 2007, A1, . Location in patent: Page/Page column 3
[3] Patent: US2012/165339, 2012, A1, . Location in patent: Page/Page column 22-23
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4648 - 4664
  • 2
  • [ 106-89-8 ]
  • [ 63106-93-4 ]
YieldReaction ConditionsOperation in experiment
68.1%
Stage #1: With sodium hydride In 1,3-dimethyl-2-imidazolidinone; toluene at 10 - 20℃; for 2 h;
Stage #2: at 10 - 20℃;
Referential Example 1:
Production of 2-oxo-1-phenyl-3-oxabicyclo[3.1.0]hexane
In a mixed solution of toluene (26.0 kg) and N,N'-dimethylimidazolidinone (94.9 kg), 60percent sodium hydride (27.2 kg; 683 mol) was added, and phenylacetonitrile (40.2 kg, 343 mol) was subsequently added dropwise thereto at 10 to 20°C.
After the resulting mixture was stirred for 2 hours, a mixture of epichlorohydrin (31.7 kg, 343 mol) and toluene (26.0 kg) was added dropwise thereto at 10 to 20°C and then stirred.
After confirming the disappearance of the raw material, methanol (22.0 kg) and water (120.6 kg) were added therein to be subjected to washing and phase separation.
24percent Aqueous solution of potassium hydroxide (159.1 kg) and tetrabutylammonium sulfate (1.1 kg) was added to the organic layer obtained, and the mixture was heated and refluxed.
After cooling down, the organic phase was removed by a phase separation.
Toluene (69.6 kg) and 35percent hydrochloric acid (78.7 kg)were further added to the aqueous phase, and then the mixture was stirred at 60 to 70°C for 2 hours.
After cooling down the mixture and subjecting to a phase separation, an organic layer was further washed twice with 8percent aqueous sodium hydrogen carbonate solution and twice with water.
The organic layer obtained was concentrated under a reduced pressure to obtain 40.7 kg of the titled compound in a form of light-yellow oily substance.
Yield was 68.1percent.
The obtained oily substance of 2-oxo-1-phenyl-3-oxabicyclo[3.1.0]hexane was cooled to transform to crystals.
Reference: [1] Patent: EP1770084, 2007, A1, . Location in patent: Page/Page column 4
  • 3
  • [ 68-34-8 ]
  • [ 145193-16-4 ]
  • [ 63106-93-4 ]
Reference: [1] Angewandte Chemie, International Edition, 2012, vol. 51, # 42, p. 10605 - 10609,5[2] Angewandte Chemie, 2012, vol. 124, # 24, p. 10757 - 10761,5
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 42, p. 10605 - 10609[4] Angew. Chem., 2012, vol. 124, # 24, p. 10757 - 10761,5
  • 4
  • [ 145193-16-4 ]
  • [ 63106-93-4 ]
Reference: [1] Organic Letters, 2000, vol. 2, # 8, p. 1145 - 1147
  • 5
  • [ 1797-74-6 ]
  • [ 63106-93-4 ]
Reference: [1] Organic Letters, 2000, vol. 2, # 8, p. 1145 - 1147
  • 6
  • [ 168475-91-0 ]
  • [ 33131-14-5 ]
  • [ 1575-48-0 ]
  • [ 63106-93-4 ]
  • [ 96847-64-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 11, p. 1437 - 1444
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