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[ CAS No. 3597-91-9 ] {[proInfo.proName]}

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Chemical Structure| 3597-91-9
Chemical Structure| 3597-91-9
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Product Details of [ 3597-91-9 ]

CAS No. :3597-91-9 MDL No. :MFCD00004660
Formula : C13H12O Boiling Point : -
Linear Structure Formula :- InChI Key :AXCHZLOJGKSWLV-UHFFFAOYSA-N
M.W : 184.23 Pubchem ID :19186
Synonyms :

Calculated chemistry of [ 3597-91-9 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.08
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 58.01
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.32
Log Po/w (XLOGP3) : 3.38
Log Po/w (WLOGP) : 2.69
Log Po/w (MLOGP) : 3.08
Log Po/w (SILICOS-IT) : 3.42
Consensus Log Po/w : 2.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.61
Solubility : 0.0448 mg/ml ; 0.000243 mol/l
Class : Soluble
Log S (Ali) : -3.48
Solubility : 0.0605 mg/ml ; 0.000329 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.74
Solubility : 0.00332 mg/ml ; 0.000018 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.36

Safety of [ 3597-91-9 ]

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 [ 3597-91-9 ]

* 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 [ 3597-91-9 ]
  • Downstream synthetic route of [ 3597-91-9 ]

[ 3597-91-9 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 3597-91-9 ]
  • [ 37729-18-3 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 42, p. 9832 - 9839
  • 2
  • [ 3597-91-9 ]
  • [ 2567-29-5 ]
YieldReaction ConditionsOperation in experiment
95% With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1.5 h; Carbon tetrabromide (8.99 g, 27.1 MMOL) and triphenyl phosphine (7.11 g, 27.1 MMOL) were added to a stirred solution of biphenyl-4-yl methanol (5.00 g, 27.1 MMOL) in dichloromethane (100 mL) at room temperature. Stirring was continued at room temperature for 1.5 hours then the solvent removed by evaporation under reduced pressure. The residue was purified by column chromatography on silica gel (1: 20 diethyl ether: cyclohexane) to give the title compound (6.37g, 95percent) as a white solid.'H NMR (400 MHz: CDCI3) : 7.6 (4 H), 7.45 (4 H), 7.35 (1 H), 4.55 (2 H).
95% With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1.5 h; Carbon tetrabromide (8.99 g, 27.1 mmol) and triphenyl phosphine (7.11 g, 27.1 mmol) wereadded to a stirred solution of biphenyl-4-yl methanol (5.00 g, 27.1 mmol) indichloromethane (100 ml_) at room temperature. Stirring was continued at room temperaturefor 1.5 hours then the solvent removed by evaporation under reduced pressure. Theresidue was purified by column chromatography on silica gel (1:20 diethyl ether:cyclohexane) to give the title compound (6.37g, 95percent) as a white solid. 1H NMR (400 MHz:CDCI3): 7.6 (4 H), 7.45 (4 H), 7.35 (1 H), 4.55 (2 H).
91% With phosphorus pentoxide; potassium bromide In acetonitrile at 20℃; for 1 h; General procedure: To a mixture of alcohol (1 mmol) and KBr (1.5 mmol, 0.18 g) in acetonitrile (5 mL), P2O5 (1.5 mmol, 0.23 g) was added and the reaction was stirred at room temperature for the time specified in Table 3. After reaction completion (TLC or GC), the reaction mixture was filtered and the residue washed with ethyl acetate (3 × 8 mL). The combined organic layers were washed with water (10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to afford the corresponding product. If necessary, further purification was performed by column chromatography.
75% With phosphorus tribromide In chloroform; di-isopropyl ether Reference Example 50
4-Phenylbenzyl Bromide
To a solution of 4-phenylbenzyl alcohol (1.00 g, 5.43 mmol) in a mixture of diisopropyl ether (10 mL) and chloroform (20 mL) was added phosphorus tribromide (0.98 g, 3.62 mmol) with ice-cooling and the mixture was stirred at room temperature for 1 hour.
This reaction mixture was diluted with water and extracted with diisopropyl ether.
The organic layer was washed with water and saturated aqueous sodium hydrogen carbonate solution, dried over MgSO4, and filtered.
The filtrate was concentrated under reduced pressure and the residue was recrystallized from ethanol-hexane to provide 1.00 g of the title compound.
Yield 75percent.
m.p. 86-88° C.
1H-NMR (CDCl3) δ: 4.55 (2H, s), 7.32-7.67 (9H, m).

Reference: [1] Organic Letters, 2013, vol. 15, # 9, p. 2210 - 2213
[2] Patent: WO2005/26120, 2005, A1, . Location in patent: Page/Page column 21
[3] Patent: WO2004/110974, 2004, A1, . Location in patent: Page 22
[4] Organic Letters, 2012, vol. 14, # 21, p. 5428 - 5431,4
[5] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064
[6] Tetrahedron Letters, 2016, vol. 57, # 2, p. 168 - 171
[7] Recueil des Travaux Chimiques des Pays-Bas, 1993, vol. 112, # 10, p. 535 - 548
[8] Tetrahedron Asymmetry, 1993, vol. 4, # 9, p. 2025 - 2026
[9] Organic Letters, 2012, vol. 14, # 11, p. 2754 - 2757
[10] Tetrahedron Letters, 2001, vol. 42, # 32, p. 5571 - 5573
[11] Patent: US6248766, 2001, B1,
[12] Carbohydrate Research, 1982, vol. 105, p. 168 - 172
[13] Mendeleev Communications, 2007, vol. 17, # 2, p. 82 - 84
[14] Helvetica Chimica Acta, 1952, vol. 35, p. 1348,1351
[15] Journal of Organic Chemistry, 1961, vol. 26, p. 2662 - 2667
[16] Journal of Organic Chemistry, 1980, vol. 45, # 25, p. 5177 - 5183
[17] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1991, # 12, p. 2067 - 2080
[18] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1757 - 1763
[19] Tetrahedron, 2002, vol. 58, # 17, p. 3361 - 3370
[20] European Journal of Medicinal Chemistry, 2005, vol. 40, # 6, p. 563 - 581
[21] Journal of the American Chemical Society, 2001, vol. 123, # 51, p. 12832 - 12836
[22] Patent: WO2006/90235, 2006, A1, . Location in patent: Page/Page column 46
[23] Patent: US6399629, 2002, B1,
[24] Patent: US2008/194565, 2008, A1, . Location in patent: Page/Page column 17
[25] Patent: US2003/225158, 2003, A1, . Location in patent: Page 22-23
[26] Organic Letters, 2013, vol. 15, # 22, p. 5818 - 5821
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