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[ CAS No. 3462-95-1 ] {[proInfo.proName]}

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Chemical Structure| 3462-95-1
Chemical Structure| 3462-95-1
Structure of 3462-95-1 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 3462-95-1 ]

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Product Details of [ 3462-95-1 ]

CAS No. :3462-95-1 MDL No. :MFCD00031637
Formula : C25H21ClFP Boiling Point : -
Linear Structure Formula :- InChI Key :CBHDAHHYMRXLIP-UHFFFAOYSA-M
M.W : 406.86 Pubchem ID :2733554
Synonyms :

Calculated chemistry of [ 3462-95-1 ]

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.04
Num. rotatable bonds : 5
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 121.31
TPSA : 13.59 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.8
Log Po/w (XLOGP3) : 7.02
Log Po/w (WLOGP) : 2.59
Log Po/w (MLOGP) : 7.06
Log Po/w (SILICOS-IT) : 6.57
Consensus Log Po/w : 4.49

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -7.09
Solubility : 0.0000331 mg/ml ; 0.0000000814 mol/l
Class : Poorly soluble
Log S (Ali) : -7.12
Solubility : 0.0000308 mg/ml ; 0.0000000756 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -10.69
Solubility : 0.0000000083 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.33

Safety of [ 3462-95-1 ]

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

Application In Synthesis of [ 3462-95-1 ]

* 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 [ 3462-95-1 ]
  • Downstream synthetic route of [ 3462-95-1 ]

[ 3462-95-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 603-35-0 ]
  • [ 352-11-4 ]
  • [ 3462-95-1 ]
YieldReaction ConditionsOperation in experiment
82% for 48 h; Reflux General procedure: The synthesis of trans-3a is used as an example: a mixture of 4.0g (2.78mmol) of 4-fluorobenzyl chloride and 8.73g (3.30mmol) triphenylphosphine in 12mL of benzene was refluxed for 2 days to yield white solid. Collect the solid by suction filtration and (4-fluorobenzyl)-triphenylphosphonium salt was obtained in 82percent yield. Afterward, a mixture of 9.97g (2.5mmol) of the previous salt, 2.37g (2.2mmol) of benzaldehyde, and 0.82g (3.11mmol) of 18-crown-6 in 56mL of dichloromethane was stirred violently and 27mL of 50percent aqueous solution of K2CO3 was added slowly. After addition, the reaction was stirred at room temperature for 3 days. And then the reaction mixture was poured into water and extracted with ethyl acetate for three times. The organic layers were combined and dried with anhydrous MgSO4. The organic solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1:10) to afford cis and trans-3a in a 95.1percent yield. Refluxing the previous mixture with catalytic iodine in benzene for 3h and then purify the resulting products by column chromatography on silica gel (ethyl acetate/hexane=1:10) afforded trans-3a in 92percent yield.
30% Reflux General procedure: To a solution of substituted benzyl halide in toluene was added triphenylphosphine (1.5 eq) and the mixture was refluxed. After cooling, the precipitate was filtered to give the target compound.
Reference: [1] Tetrahedron, 2013, vol. 69, # 35, p. 7325 - 7332
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 3041 - 3045
[3] Journal of Organic Chemistry, 1993, vol. 58, # 21, p. 5643 - 5649
[4] Medicinal Chemistry Research, 2011, vol. 20, # 8, p. 1158 - 1163
[5] Medicinal Chemistry Research, 2011, vol. 20, # 8, p. 1349 - 1356
[6] Tetrahedron Letters, 2013, vol. 54, # 15, p. 1991 - 1993
  • 2
  • [ 459-56-3 ]
  • [ 603-35-0 ]
  • [ 3462-95-1 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 21, p. 5643 - 5649
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