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Chemical Structure| 91-01-0
Chemical Structure| 91-01-0
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Product Details of [ 91-01-0 ]

CAS No. :91-01-0 MDL No. :MFCD00004488
Formula : C13H12O Boiling Point : -
Linear Structure Formula :- InChI Key :QILSFLSDHQAZET-UHFFFAOYSA-N
M.W : 184.23 Pubchem ID :7037
Synonyms :
Diphenylmethanol

Calculated chemistry of [ 91-01-0 ]

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 : 57.06
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 2.67
Log Po/w (WLOGP) : 2.44
Log Po/w (MLOGP) : 3.08
Log Po/w (SILICOS-IT) : 3.11
Consensus Log Po/w : 2.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.17
Solubility : 0.126 mg/ml ; 0.000681 mol/l
Class : Soluble
Log S (Ali) : -2.75
Solubility : 0.33 mg/ml ; 0.00179 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.39
Solubility : 0.00754 mg/ml ; 0.0000409 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 91-01-0 ]

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 [ 91-01-0 ]

* 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 [ 91-01-0 ]
  • Downstream synthetic route of [ 91-01-0 ]

[ 91-01-0 ] Synthesis Path-Upstream   1~18

  • 1
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  • [ 841-77-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1822 - 1826
[2] Tetrahedron Letters, 2013, vol. 54, # 28, p. 3688 - 3693
[3] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 2, p. 205 - 214
[4] Synthetic Communications, 2014, vol. 44, # 5, p. 600 - 609
[5] Medicinal Chemistry Research, 2014, vol. 23, # 6, p. 3207 - 3219
[6] Journal of Medicinal Chemistry, 2014, vol. 57, # 20, p. 8540 - 8562
[7] Analytical Chemistry, 2014, vol. 86, # 17, p. 8693 - 8699
[8] ChemSusChem, 2016, vol. 9, # 1, p. 67 - 74
[9] ChemSusChem, 2016, vol. 9, # 1, p. 67 - 74
[10] Journal of Chemistry, 2016, vol. 2016,
[11] Bioorganic and Medicinal Chemistry, 2018,
  • 2
  • [ 91-01-0 ]
  • [ 298-57-7 ]
Reference: [1] ChemSusChem, 2016, vol. 9, # 1, p. 67 - 74
[2] ChemSusChem, 2016, vol. 9, # 1, p. 67 - 74
  • 3
  • [ 91-01-0 ]
  • [ 750512-44-8 ]
  • [ 298-57-7 ]
Reference: [1] Synthetic Communications, 2014, vol. 44, # 5, p. 600 - 609
  • 4
  • [ 91-01-0 ]
  • [ 107-99-3 ]
  • [ 58-73-1 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 11, p. 2649 - 2660
[2] Patent: DE857502, 1950, ,
[3] Patent: US2577234, 1947, ,
[4] Zhurnal Obshchei Khimii, 1951, vol. 21, p. 570,572; engl. Ausg. S. 631, 633
[5] Chemicke Listy, 1951, vol. 45, p. 43[6] Chem.Abstr., 1951, p. 9010
  • 5
  • [ 108-01-0 ]
  • [ 776-74-9 ]
  • [ 91-01-0 ]
  • [ 58-73-1 ]
  • [ 574-42-5 ]
Reference: [1] Chemical Science, 2013, vol. 4, # 7, p. 2822 - 2827
[2] Chemical Science, 2013, vol. 4, # 7, p. 2822 - 2827
  • 6
  • [ 91-01-0 ]
  • [ 58-73-1 ]
Reference: [1] Yakugaku Zasshi, 1951, vol. 71, p. 365[2] Chem.Abstr., 1952, p. 951
[3] Res. Rep. Nagoya ind. Sci. Res. Inst., 1951, # 4, p. 87[4] Chem.Abstr., 1955, p. 218
  • 7
  • [ 108-01-0 ]
  • [ 91-01-0 ]
  • [ 58-73-1 ]
Reference: [1] DRP/DRBP Org.Chem.,
[2] Patent: US2668857, 1951, ,
  • 8
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  • [ 68-11-1 ]
  • [ 63547-22-8 ]
YieldReaction ConditionsOperation in experiment
64% at 20℃; for 3 h; Thioglycolic acid (10.5 g, 7.92 ml (d=l .325), 0.114 mol) was added dropwise to the solution of diphenylmethanol in trifuoroacetic acid (100 ml). The formation of precipitate was observed in 30 min. The reaction mixture was stirred at room temperature for 3 h. The resulting precipitate was filtered off washed with water (3> 50 ml) and hexanes. The crude product was recrystallized from EtOAc/hexanes to get colorless precipitate of 2- (Benzhydrylthio)acetic acid. Yield: 17.93 g (64percent). M.p. 121 °C. 2-(B enzhy dryl th io)acetam ide
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2984 - 2997
[2] Tetrahedron Asymmetry, 2004, vol. 15, # 6, p. 1053 - 1058
[3] Tetrahedron Asymmetry, 2005, vol. 16, # 21, p. 3507 - 3511
[4] Patent: US7553646, 2009, B2,
[5] Molecules, 2012, vol. 17, # 9, p. 10446 - 10458
[6] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 39, # 10, p. 853 - 874
[7] Journal of Organometallic Chemistry, 1996, vol. 507, # 1-2, p. 215 - 220
[8] Patent: WO2016/23997, 2016, A1, . Location in patent: Page/Page column 34
[9] Acta Chemica Scandinavica (1947-1973), 1948, vol. 2, p. 856,858
[10] Journal fuer Praktische Chemie (Leipzig), 1934, vol. <2> 141, p. 93,96[11] Arkiv foer Kemi, 1937, vol. 12 A, # 14, p. 3,4
[12] Journal fuer Praktische Chemie (Leipzig), 1934, vol. <2> 141, p. 93,96[13] Arkiv foer Kemi, 1937, vol. 12 A, # 14, p. 3,4
[14] Journal fuer Praktische Chemie (Leipzig), 1934, vol. <2> 141, p. 93,96[15] Arkiv foer Kemi, 1937, vol. 12 A, # 14, p. 3,4
[16] Patent: WO2009/90663, 2009, A1, . Location in patent: Page/Page column 8
[17] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 1, p. 48 - 52
[18] Journal of Medicinal Chemistry, 2014, vol. 57, # 3, p. 1000 - 1013
  • 9
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  • [ 89619-93-2 ]
  • [ 63547-22-8 ]
Reference: [1] Russian Chemical Bulletin, 2013, vol. 62, # 5, p. 1164 - 1175[2] Izv. Akad. Nauk, Ser. Khim., 2013, # 5, p. 1164 - 1175,12
  • 10
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  • [ 79-11-8 ]
  • [ 63547-22-8 ]
Reference: [1] Journal of Organic Chemistry, 1968, vol. 33, # 5, p. 2030 - 2035
  • 11
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  • [ 613-45-6 ]
  • [ 119-61-9 ]
  • [ 7314-44-5 ]
Reference: [1] Chemical Communications, 2018, vol. 54, # 50, p. 6883 - 6886
  • 12
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  • [ 122-52-1 ]
  • [ 27329-60-8 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 6, p. 1270 - 1273
  • 13
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  • [ 112-61-8 ]
  • [ 98-86-2 ]
  • [ 58446-52-9 ]
Reference: [1] Patent: US6410795, 2002, B1,
  • 14
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  • [ 79-11-8 ]
  • [ 63547-24-0 ]
YieldReaction ConditionsOperation in experiment
43%
Stage #1: With hydrogen bromide; thiourea In water at 60 - 90℃;
Stage #2: With sodium hydroxide In water at 70℃; Reflux
Stage #3: With dihydrogen peroxide In water at 20℃; for 3 h;
C. Synthesis of 2-(benzhydrylsulfinyl)acetic acid [00104] 10g of thiourea was dissolved in 57 mL of 48percent HBr and 10ml of water. The reaction mixture was heated to 60°C, and 20.2 g of benzhydrol was added. The temperature was increased to 90°C, and the mixture was then cooled to room temperature. The crystals were filtered off and washed with water. To the above crystals were added 35 mL 30percent sodium hydroxide. The mixture was heated to 70°C, and 11.44 g chloroacetic acid in 22 mL of water were added slowly. The mixture was reflux ed for half an hour after the addition. 14.3 mL hydrogen peroxide (30percent) was added to the above solution within 3 hours at room temperature. Water (22 ml) was added to the reaction mixture, which was then filtered. The filtrate was acidified with concentrated HC1 (d=1.18). The resulting solid was filtered and dried to give 2- (benzhydrylsulfinyl)acetic acid (13g, 43percent) as the desired product.
Reference: [1] Patent: WO2011/26240, 2011, A1, . Location in patent: Page/Page column 35; 36
  • 15
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  • [ 63547-24-0 ]
Reference: [1] Molecules, 2012, vol. 17, # 9, p. 10446 - 10458
[2] Molecules, 2012, vol. 17, # 9, p. 10446 - 10458
  • 16
  • [ 91-01-0 ]
  • [ 100-99-2 ]
  • [ 102123-74-0 ]
  • [ 165727-45-7 ]
Reference: [1] Patent: US6255522, 2001, B1,
  • 17
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  • [ 211321-08-3 ]
  • [ 186046-78-6 ]
YieldReaction ConditionsOperation in experiment
22.1 g
Stage #1: With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide
Stage #2: at 60℃; for 19.5 h;
Stage #3: With lithium hydroxide monohydrate In methanol; ethanol; water; acetonitrile at 0℃;
Cytosine (10.3 g, 90 mmol, 1.0 eq) was dissolved in DMF (90 mL).Potassium tert-butoxide (11.6 g, 103.5 mmol, 1.15 eq) was added.Thereafter, the reaction system was heated to 100 ° C for 2 hours.Cooling the reaction system to 10 ° C,Drop by drop in 30 minutesBenzyl 2-bromoacetate(16.05mL, 101mmol, 1.12eq),After the completion of the dropwise addition, the reaction system was warmed to room temperature and the reaction was continued for 12 hours.Add acetic acid (5.9 mL, 103.5 mmol, 1.2 eq) to quench the reaction.The reaction solution was spun dry.The residue was resuspended in H2O (100 mL).Continue stirring for 4 hours and then filter.Washed with H2O (4x 150mL),Cytosine-1-benzylacetic acid20.6g.Cytosine-1-benzylacetic acid (20.6 g, 82 mmol, 1.0 eq) was dissolved in DMF (160 mL).N,N'-carbonyldiimidazole (21.25 g, 131.25 mmol, 1.6 eq) was added.After the TLC detection reaction was completed, methanol was added.Continue to stir for 1.5 hours.Diphenylmethanol (19.65 g, 106.5 mmol, 1.3 eq) was added.The reaction system is heated to 60 ° C,After two batchesDiphenylmethanol (2 x 1.825 g, 9.9 mmol, 0.12 eq) was added at 1 hour intervals.Continue to react for 6 hours.Stop heating for 12 hours,The reaction was quenched by the addition of methanol (4.65 g, 115 mmol, 1.4 eq).Spin the reaction solution,The residue continues to recrystallize with ethanol,After recrystallization from methanol (100 mL), (4-N-(diphenylmethoxycarbonyl)-cytosyl)-1-acetate29.35g.Taking (4-N-(diphenylmethoxycarbonyl)-cytosine)-1-acetate29.35 g, 62.5 mmol, 1.0 eq) in a mixed solution of acetonitrile: MeOH:H 2 O: EtOH (2:2:1:1, 350 mL),Heating to dissolve the compound,After cooling to 0 ° C,An aqueous solution (196.8 mL) of LiOH.H 2 O (25.5 g, 0.61 mol, 9.7 eq) was added.TLC detected that the reaction was complete and then added citric acid (58.5 g,An aqueous solution (290 mL) of 303.5, 4.9 eq) was quenched.Obtaining (4-N-(diphenylmethoxycarbonyl)-cytosine)-1-acetic acid22.1g.
Reference: [1] Patent: CN108478807, 2018, A, . Location in patent: Paragraph 0023; 0053; 0077; 0078
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  • [ 135248-89-4 ]
  • [ 247595-29-5 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 21, p. 5472 - 5475,4
[2] Organic Letters, 2012, vol. 14, # 21, p. 5472 - 5475
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