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[ CAS No. 247940-06-3 ] {[proInfo.proName]}

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Chemical Structure| 247940-06-3
Chemical Structure| 247940-06-3
Structure of 247940-06-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 247940-06-3 ]

CAS No. :247940-06-3 MDL No. :MFCD01862441
Formula : C24H31P Boiling Point : -
Linear Structure Formula :- InChI Key :LCSNDSFWVKMJCT-UHFFFAOYSA-N
M.W : 350.48 Pubchem ID :2734216
Synonyms :
2-(Dicyclohexylphosphino)biphenyl

Calculated chemistry of [ 247940-06-3 ]

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.5
Num. rotatable bonds : 4
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 114.0
TPSA : 13.59 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.28
Log Po/w (XLOGP3) : 6.74
Log Po/w (WLOGP) : 7.13
Log Po/w (MLOGP) : 6.33
Log Po/w (SILICOS-IT) : 7.23
Consensus Log Po/w : 6.34

Druglikeness

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

Water Solubility

Log S (ESOL) : -6.35
Solubility : 0.000156 mg/ml ; 0.000000446 mol/l
Class : Poorly soluble
Log S (Ali) : -6.83
Solubility : 0.0000518 mg/ml ; 0.000000148 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -7.86
Solubility : 0.00000487 mg/ml ; 0.0000000139 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.31

Safety of [ 247940-06-3 ]

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 [ 247940-06-3 ]

* 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 [ 247940-06-3 ]
  • Downstream synthetic route of [ 247940-06-3 ]

[ 247940-06-3 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 2052-07-5 ]
  • [ 829-84-5 ]
  • [ 247940-06-3 ]
YieldReaction ConditionsOperation in experiment
81% With bis(η3-allyl-μ-chloropalladium(II)); potassium hydroxide In water at 100℃; Inert atmosphere General procedure: A mixture of L1 (0.05 or 0.10 mmol of P), [PdCl(η3-C3H5)]2 (0.025mmol), arylhalides (0.55 mmol) and dicyclohexylphosphine (0.50 mmol) in 20 M KOH aqueous solution (0.5-1.0 mL) under nitrogen atmosphere was shaken for several hours at 100 °C. The mixture was cooled and filtered. After being cooled, the reaction mixture was filtered and the aqueous filtrate was extracted with degassed toluene (2 mL x 2 times). Recovered catalyst resin beads were extracted with degassed toluene (2 mL x 4 times). The combined extract was dried over anhydrous Na2SO4 and concentrated in vacuo to give a crude residue. The residue was purified by silica-gel flash chromatography to give an aryl dicyclohexylphosphine 3. Chromatographic purification was carried out with the YAMAZEN medium pressure liquid chromatograph system using degassed eluent (n-hexane/Et2O = 10/0-9/1).
Reference: [1] Synlett, 2017, vol. 28, # 20, p. 2966 - 2970
  • 2
  • [ 17763-65-4 ]
  • [ 829-84-5 ]
  • [ 247940-06-3 ]
YieldReaction ConditionsOperation in experiment
77% With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 100℃; for 18.67 h; A 50 cc glass vessel was equipped with a magnetic stirring bar, a pressure gauge, a syringe loading opening, a nitrogen valve and a vacuum valve. To the glass vessel were added 3.08 g (10.2 mmol) of biphenyl-2-yl-triflate, 3.12 g (20.5 mmol) of DBU, 262.7 mg (0.50 mmol) of Ni(dppe)Cl2, 20 cc of DMF and 2.98 g (15.0 mmol) of dicyclohexylphosphine under a nitrogen atmosphere. The reaction mixture was stirred and aged overnight (18 hours and 40 minutes) in an oil bath at 100° C. under a nitrogen atmosphere.The reaction solution was concentrated, and to the residue were added 20 cc of toluene and 10 g of 5percent hydrochloric acid, followed by shaking and separating. The resulting organic layer was washed with 10 cc of water, 20 g of 2.5percent sodium bicarbonate aqueous solution and 10 cc of water in this order. The organic layer was returned to a reaction flask, followed by concentrating to obtain a colored oil. The resulting colored oil was recrystallized and purified with 20 cc of methanol to obtain colorless powders (yield amount: 2.74 g (7.82 mmol)), yield: 77percent). The resulting colorless powders were confirmed to be 2-(dicyclohexylphosphino)biphenyl, which was an intended product. The analytical results of the resulting colorless powders are shown below. Quality: GC purity 98.0percent Characteristics: GC-MS: 349, 350 (FW350.48), mp: 103.4 to 104.6° C. 1H-NMR (CDCl3); 0.95-1.30 (10H, m), 1.50-1.75 (10H, m), 1.75-1.90 (2H, m), 7.25-7.44 (8H, m), 7.56-7.74 (1H, m) 31P-NMR; -12.6
8 %Chromat. With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 100℃; for 18.67 h; A biphenyl-2-yl phosphine compounds were obtained in the same manner as Example 1 except for changing the type of a hydrogen-phosphine compound, catalyst, base and solvent used, as shown in Table 1.In addition, in all the Examples and Comparative Examples, biphenyl-2-yl-triflate was used as a biarylsulfonate compound, and 1.5 equivalents of a hydrogen-phosphine compound and 2 equivalents of a base were used, based on biphenyl-2-yl-triflate. Further, the reaction time was set to 16 to 24 hours (overnight).In Examples 1 to 5 and Comparative Examples 1 to 3, the compounds used and the results of the reaction yield and the like are shown in Table 1.
90 %Chromat. With 1,8-diazabicyclo[5.4.0]undec-7-ene In water; N,N-dimethyl-formamide at 100℃; for 18.67 h; A biphenyl-2-yl phosphine compounds were obtained in the same manner as Example 1 except for changing the type of a hydrogen-phosphine compound, catalyst, base and solvent used, as shown in Table 1.In addition, in all the Examples and Comparative Examples, biphenyl-2-yl-triflate was used as a biarylsulfonate compound, and 1.5 equivalents of a hydrogen-phosphine compound and 2 equivalents of a base were used, based on biphenyl-2-yl-triflate. Further, the reaction time was set to 16 to 24 hours (overnight).In Examples 1 to 5 and Comparative Examples 1 to 3, the compounds used and the results of the reaction yield and the like are shown in Table 1.
Reference: [1] Patent: US2009/54690, 2009, A1, . Location in patent: Page/Page column 6-7
[2] Patent: US2009/54690, 2009, A1, . Location in patent: Page/Page column 6-7
[3] Patent: US2009/54690, 2009, A1, . Location in patent: Page/Page column 6-7
  • 3
  • [ 2052-07-5 ]
  • [ 16523-54-9 ]
  • [ 247940-06-3 ]
Reference: [1] Journal of the American Chemical Society, 1999, vol. 121, # 41, p. 9550 - 9561
[2] Organic Letters, 2013, vol. 15, # 24, p. 6186 - 6189
  • 4
  • [ 67-56-1 ]
  • [ 1186392-99-3 ]
  • [ 121-43-7 ]
  • [ 247940-06-3 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 32, p. 6410 - 6415
  • 5
  • [ 583-55-1 ]
  • [ 247940-06-3 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 24, p. 6186 - 6189
[2] Chemical Communications, 2014, vol. 50, # 17, p. 2193 - 2195
  • 6
  • [ 98-80-6 ]
  • [ 247940-06-3 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 24, p. 6186 - 6189
[2] Chemical Communications, 2014, vol. 50, # 17, p. 2193 - 2195
  • 7
  • [ 64-17-5 ]
  • [ 1186392-99-3 ]
  • [ 150-46-9 ]
  • [ 247940-06-3 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 32, p. 6410 - 6415
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