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[ CAS No. 161265-03-8 ] {[proInfo.proName]}

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Chemical Structure| 161265-03-8
Chemical Structure| 161265-03-8
Structure of 161265-03-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 161265-03-8 ]

CAS No. :161265-03-8 MDL No. :MFCD00233866
Formula : C39H32OP2 Boiling Point : -
Linear Structure Formula :- InChI Key :CXNIUSPIQKWYAI-UHFFFAOYSA-N
M.W : 578.62 Pubchem ID :636044
Synonyms :

Calculated chemistry of [ 161265-03-8 ]

Physicochemical Properties

Num. heavy atoms : 42
Num. arom. heavy atoms : 36
Fraction Csp3 : 0.08
Num. rotatable bonds : 6
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 182.88
TPSA : 36.41 Ų

Pharmacokinetics

GI absorption : Low
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) : -2.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 5.48
Log Po/w (XLOGP3) : 9.7
Log Po/w (WLOGP) : 7.63
Log Po/w (MLOGP) : 7.77
Log Po/w (SILICOS-IT) : 11.07
Consensus Log Po/w : 8.33

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -9.78
Solubility : 0.0000000968 mg/ml ; 0.0000000002 mol/l
Class : Poorly soluble
Log S (Ali) : -10.38
Solubility : 0.000000024 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -15.7
Solubility : 0.0 mg/ml ; 1.98e-16 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 5.68

Safety of [ 161265-03-8 ]

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 [ 161265-03-8 ]

* 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 [ 161265-03-8 ]
  • Downstream synthetic route of [ 161265-03-8 ]

[ 161265-03-8 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 4175-77-3 ]
  • [ 161265-03-8 ]
  • [ 141305-40-0 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 23, p. 8471 - 8482
  • 2
  • [ 19814-75-6 ]
  • [ 1079-66-9 ]
  • [ 161265-03-8 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tert-butyl methyl ether; cyclohexane at 6 - 10℃;
Stage #2: at 20℃; for 14 h;
Stage #3: at 10 - 20℃; for 5.16667 h;
Example 2A
Preparation of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, Xantphos
To a 5L round bottom flask (RBF) are added MTBE (2.5 L), 9,9-dimethylxanthene (131.4 g, 0.60 mole) and TMEDA (155 g, 1.32 mole).
After degassing the solution, s-BuLi (1.11 L, 1.3 M in cyclohexane, 1.44 mole) is cannulated into a dropping funnel and then slowly added over 60 min while maintaining the batch temperature at 6-10° C.
The mixture is then aged for 14 h at room temperature.
Ph2PCl is added slowly via a dropping funnel while maintain the mildly exothermic reaction at 10-20° C.
~60percent of the Ph2PCl (175 mL, 0.93 mole) is added in 0.5 hour.
The mixture is aged for 10 minutes before addition of the remaining Ph2PCl (120 mL, 0.63 mole).
After aged for 5 h at room temperature, the reaction is quenched with MeOH (9.9 mL, 0.24 mole).
The product is filtered and the slightly yellow solid is washed consecutively with MTBE (250 mL), MeOH (2*250 mL), water (2*300 mL), MeOH (2*250 mL) and MTBE (250 mL) and dried to give an off-white solid as product (304.2 g, 88percent yield).
77%
Stage #1: With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tert-butyl methyl ether; cyclohexane at 10 - 20℃; for 16 h;
Stage #2: at 20℃; for 5.75 h;
Example 2
Preparation of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, Xantphos
To a 1L round bottom flask (RBF) are added MTBE (500 mL), 9,9-dimethylxanthene (26.65 g) and TMEDA (30.6 g).
After degassing the solution, s-BuLi (155 g, 1.3 M in cyclohexane) is cannulated into a dropping funnel and then slowly added over 30 min while maintaining the batch temperature at 10-20° C.
The mixture is then aged for 16 h at room temperature.
Ph2PCl is added slowly via a dropping funnel while maintain the mildly exothermic reaction at 10-20° C.
~60percent of the Ph2PCl (30 mL) is added in 0.5 hour.
The mixture is aged for 15 minutes before addition of the remaining Ph2PCl.
After aged for 5.5 h at room temperature, the reaction is quenched with MeOH (2.0 mL).
The product is filtered and the slightly yellow solid is washed consecutively with MeOH (200 mL), water (200 mL), MeOH (200 mL) and MTBE (200 mL) and dried to give an off-white solid as product (54.8 g, 77percent yield).
Reference: [1] Patent: US2004/23979, 2004, A1, . Location in patent: Page/Page column 9; 10
[2] Patent: US2004/23979, 2004, A1, . Location in patent: Page/Page column 9
[3] Dalton Transactions, 2018, vol. 47, # 11, p. 3745 - 3754
[4] Tetrahedron Letters, 1995, vol. 36, # 1, p. 75 - 78
[5] Patent: US7612241, 2009, B1, . Location in patent: Page/Page column 4-5
[6] Patent: US2004/23978, 2004, A1, . Location in patent: Page/Page column 15;16
[7] Patent: US2004/23981, 2004, A1, . Location in patent: Page/Page column 17
[8] Dyes and Pigments, 2012, vol. 94, # 3, p. 561 - 569
  • 3
  • [ 19814-75-6 ]
  • [ 161265-03-8 ]
Reference: [1] Patent: US2004/23980, 2004, A1, . Location in patent: Page/Page column 15
  • 4
  • [ 808142-24-7 ]
  • [ 161265-03-8 ]
Reference: [1] ChemCatChem, 2017, vol. 9, # 24, p. 4460 - 4464
[2] Chemistry - A European Journal, 2017, vol. 23, # 58, p. 14434 - 14438
  • 5
  • [ 21264-30-2 ]
  • [ 161265-03-8 ]
  • [ 205319-10-4 ]
Reference: [1] Organic Syntheses, 2016, vol. 93, p. 341 - 351
[2] Organic Syntheses, 2016, vol. 93, p. 341 - 351
[3] Journal of the American Chemical Society, 2015, vol. 137, # 39, p. 12490 - 12493
  • 6
  • [ 15617-18-2 ]
  • [ 161265-03-8 ]
  • [ 205319-10-4 ]
Reference: [1] European Journal of Inorganic Chemistry, 1998, # 2, p. 155 - 157
  • 7
  • [ 161265-03-8 ]
  • [ 205319-10-4 ]
Reference: [1] Journal of Organometallic Chemistry, 2012, vol. 696, # 26, p. 4293 - 4297
  • 8
  • [ 1435520-65-2 ]
  • [ 161265-03-8 ]
  • [ 1445085-97-1 ]
Reference: [1] Chemical Science, 2013, vol. 4, # 3, p. 916 - 920
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