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[ CAS No. 76-84-6 ] {[proInfo.proName]}

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Chemical Structure| 76-84-6
Chemical Structure| 76-84-6
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Product Details of [ 76-84-6 ]

CAS No. :76-84-6 MDL No. :MFCD00004445
Formula : C19H16O Boiling Point : -
Linear Structure Formula :- InChI Key :LZTRCELOJRDYMQ-UHFFFAOYSA-N
M.W : 260.33 Pubchem ID :6457
Synonyms :
Triphenylmethyl alcohol;Triphenylmethanol

Calculated chemistry of [ 76-84-6 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.05
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 81.43
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 : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.83
Log Po/w (XLOGP3) : 3.68
Log Po/w (WLOGP) : 3.86
Log Po/w (MLOGP) : 4.33
Log Po/w (SILICOS-IT) : 4.41
Consensus Log Po/w : 3.82

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.24
Solubility : 0.015 mg/ml ; 0.0000575 mol/l
Class : Moderately soluble
Log S (Ali) : -3.79
Solubility : 0.0418 mg/ml ; 0.00016 mol/l
Class : Soluble
Log S (SILICOS-IT) : -6.91
Solubility : 0.0000322 mg/ml ; 0.000000124 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.98

Safety of [ 76-84-6 ]

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 [ 76-84-6 ]

* 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 [ 76-84-6 ]
  • Downstream synthetic route of [ 76-84-6 ]

[ 76-84-6 ] Synthesis Path-Upstream   1~29

  • 1
  • [ 288-32-4 ]
  • [ 76-84-6 ]
  • [ 102-10-3 ]
  • [ 15469-97-3 ]
YieldReaction ConditionsOperation in experiment
82.7% With pyridine In acetonitrile EXAMPLE 11
Preparation of 1-triphenylmethylimidazole
A mixture of pyridine (15 ml), diphenyl phosphite (2.34 g, 10 mmole), imidazole (0.68 g, 10 mmole) and triphenylmethanol (2.08 g, 8 mmole) was refluxed for 3 hours.
Pyridine was removed under reduced pressure, and the residue was extracted with dichloromethane.
The extract was washed with a 5percent aqueous hydroxide solution and water in order, dried and evaporated.
Recrystallization of the residue (2.23 g) from acetonitrile gave 2.05 g of 1-triphenylmethylimidazole as colorless needles.
Yield, 82.7percent. M.P., 221°-223° C.
Elementary analysis: Calcd. for C22 H18 N2: C, 85.13percent; H, 5.85percent; N, 9.03percent. Found: C, 85.20percent; H, 6.03percent; N, 9.21percent.
Reference: [1] Patent: US4216333, 1980, A,
  • 2
  • [ 288-32-4 ]
  • [ 76-84-6 ]
  • [ 15469-97-3 ]
Reference: [1] Patent: US6051573, 2000, A,
  • 3
  • [ 76-84-6 ]
  • [ 15469-97-3 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 1992, vol. 42, # 6, p. 832 - 835
  • 4
  • [ 75759-62-5 ]
  • [ 76-84-6 ]
  • [ 4546-72-9 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 26, p. 2641 - 2644
  • 5
  • [ 7732-18-5 ]
  • [ 76-84-6 ]
  • [ 126-58-9 ]
Reference: [1] Chemische Berichte, 1930, vol. 63, p. 2684
  • 6
  • [ 76-84-6 ]
  • [ 25603-67-2 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 4, p. 1365 - 1370
[2] Journal of the American Chemical Society, 1971, vol. 93, # 23, p. 6158 - 6166
[3] Chemische Berichte, 1905, vol. 38, p. 292
[4] Chemische Berichte, 1905, vol. 38, p. 292
  • 7
  • [ 76-84-6 ]
  • [ 25603-67-2 ]
  • [ 519-73-3 ]
  • [ 789-24-2 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 4, p. 807 - 810
  • 8
  • [ 76-84-6 ]
  • [ 21947-98-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 383 - 392
[2] Chemical Communications, 2013, vol. 49, # 92, p. 10808 - 10810
  • 9
  • [ 76-84-6 ]
  • [ 58632-95-4 ]
  • [ 52-89-1 ]
  • [ 21947-98-8 ]
Reference: [1] Canadian Journal of Chemistry, 1979, vol. 57, p. 1388 - 1396
  • 10
  • [ 76-84-6 ]
  • [ 107-96-0 ]
  • [ 27144-18-9 ]
YieldReaction ConditionsOperation in experiment
90% With sulfuric acid; acetic acid In tetrahydrofuran at 28 - 30℃; for 4 h; 100 g of 3-thiopropionic acid (106.14 942.15 nmol) was dissolved in 300 ml of glacial acetic acid at room temperature,B. 245.27 g Trt-OH (260.33 942.15 nmol) was dissolved in 736.79 ml THF at room temperature,C. A step of the product is slowly added to the product of step b,D. 28 ° C-30 ° C was added dropwise 16.62 g of concentrated sulfuric acid (98 169.587 nmol)E. Insulation reaction 4 hours,F. The reaction gave a solid which was filtered to give 360 g of crude product which was dissolved in 720 ml of DMF,G. Plus 5 times the amount of water system, the filter was dried boutique295.5g yield90percent. By infrared, nuclear magnetic structure is positiveIndeed, see Figure 1, Figure 2.
Reference: [1] Organic Letters, 2017, vol. 19, # 12, p. 3195 - 3198
[2] Patent: CN106380430, 2017, A, . Location in patent: Paragraph 0017; 0018; 0019; 0020
[3] Chemical Communications, 2014, vol. 50, # 35, p. 4571 - 4574
[4] Australian Journal of Chemistry, 1990, vol. 43, # 3, p. 629 - 634
[5] Journal of Medicinal Chemistry, 2000, vol. 43, # 8, p. 1448 - 1455
[6] Chemistry - A European Journal, 2008, vol. 14, # 19, p. 5908 - 5917
[7] Patent: WO2007/75931, 2007, A2, . Location in patent: Page/Page column 42-43
  • 11
  • [ 76-84-6 ]
  • [ 107-96-0 ]
  • [ 27144-18-9 ]
YieldReaction ConditionsOperation in experiment
90% With potassium hydrogensulfate In sodium hydrogencarbonate; N,N-dimethyl-formamide STEP A).
Preparation of 3-Tritylthio-propionic Acid
A solution of 0.87 ml (10 mmol) 3-mercaptopropionic acid and 2.86 g (11 mmol) triphenylmethanol in 40 ml N,N-dimethylformamide (AMF) was stirred for 30 min at 60° C.
After the solution was cooled to ambient temperature, 1.43 ml (11.4 mmol) borontrifluor etherate was added and the reaction mixture was stirred at 60° C. for 4 hr.
The solution was concentrated in vacuo and the residue was dissolved in 500 ml 5percent NaHCO3.
The aqueous solution was washed with 250 ml diethyl ether, acidified to pH 3 using 1 M KHSO4, and extracted twice with 500 ml ethyl acetate.
The combined ethyl acetate fractions were washed with 250 ml brine and dried over Na2SO4.
The product was obtained as a white solid in 90percent yield.
1H-NMR (CDCl3) δ 2.23 (t, 2H, CH2S), 2.46 (t, 2H, CH2COOH), 7.23-7.43 (m, 15H, Trt)
Reference: [1] Patent: US6958212, 2005, B1,
  • 12
  • [ 76-84-6 ]
  • [ 27144-18-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1970, vol. 13, p. 414 - 418
  • 13
  • [ 76-84-6 ]
  • [ 52-89-1 ]
  • [ 2799-07-7 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: for 2 h;
Stage #2: With sodium acetate; sodium hydroxide In diethyl ether; water at 0℃;
Triphenylmethanol (3.3 g, 12.7 mmol) was added to a solution of Cysteine chlorydrate (2 g, 12.7 mmol) in TFA (25 mL) and the mixture was stirred for 2 h. After cooling to 0 °C, NaOH 4N and diethyl ether (40 mL) were added until pH 4-5 and then 10percent sodium acetate aqueous solution was added until pH 5-6. The precipitated obtained was filtered, washed with fresh Et2O and finally dried to obtain the desired product (5 g, 98percent yield).1H NMR (DMSO): δ (ppm) 2.35-2.61 (m, 2H, CH2); 2.85-2.98 (m, 1H, CH); 7.2-7.45 (m, 15H, trityl-H).MALDI-TOF MS: m/z364.7 Da [M + H]+, C22H21NO2S, Mol. Wt.: 363.47.
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 383 - 392
[2] Chemical Communications, 2013, vol. 49, # 92, p. 10808 - 10810
[3] Journal of the Chemical Society [Section] C: Organic, 1970, p. 2687
[4] Journal of Medicinal Chemistry, 1970, vol. 13, p. 414 - 418
[5] Canadian Journal of Chemistry, 1981, vol. 59, # 2, p. 406 - 421
  • 14
  • [ 76-84-6 ]
  • [ 52-90-4 ]
  • [ 2799-07-7 ]
YieldReaction ConditionsOperation in experiment
90% at 20℃; for 5 h; To a solution of l-cysteine (1.0 g, 5.69 mmol) in acetic acid (15 mL) was added triphenyl methanol (1.64 g, 6.30 mmol), followed by adding trifluoroboron ethylether (720 μL, 5.69 mmol) dropwise and the reaction was stirred at room temperature. After 5 h, the reaction mixture was neutralized with saturated sodium acetate. The resulting precipitate was washed with ethylether and collected to give the desired compound 3 (1.87 g, 90percent) as a white solid. 1H NMR (300 MHz, acetone-d6): δ = 7.46-7.23 (m, 15H), 3.64 (dd, J = 8.10 Hz, 4.20 Hz, 1H), 2.67-2.52 (m, 2H). 13C NMR (75 MHz, DMSO-d6): δ = 169.89, 144.42, 129.25, 128.11, 126.78, 65.95, 53.64, 34.39. MALDI-TOF-MS: Calcd for C22H20NO2S 362.1. Found 362.1 [M-H]-.
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 11, p. 3465 - 3469
  • 15
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  • [ 55135-66-5 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 292
  • 16
  • [ 76-84-6 ]
  • [ 70-47-3 ]
  • [ 132388-58-0 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 6, p. 739 - 742
[2] Organic Letters, 2002, vol. 4, # 21, p. 3767 - 3769
[3] Patent: WO2004/7427, 2004, A1, . Location in patent: Page 51-52
  • 17
  • [ 76-84-6 ]
  • [ 132388-58-0 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 6, p. 739 - 742
  • 18
  • [ 76-84-6 ]
  • [ 56-85-9 ]
  • [ 102747-84-2 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 6, p. 739 - 742
  • 19
  • [ 76-84-6 ]
  • [ 102747-84-2 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 6, p. 739 - 742
[2] Journal of the American Chemical Society, 2013, vol. 135, # 35, p. 12998 - 13007
  • 20
  • [ 76-84-6 ]
  • [ 132388-68-2 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 6, p. 739 - 742
[2] Tetrahedron Letters, 1991, vol. 32, # 6, p. 739 - 742
  • 21
  • [ 76-84-6 ]
  • [ 132388-69-3 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 6, p. 739 - 742
[2] Tetrahedron Letters, 1991, vol. 32, # 6, p. 739 - 742
  • 22
  • [ 76-84-6 ]
  • [ 2650-64-8 ]
  • [ 132388-60-4 ]
YieldReaction ConditionsOperation in experiment
70% at 50℃; for 2 h; (S)-5-amino-2-(((benzyloxy)carbonyl)amino)-5-oxopentanoic acid 2 (11.20 g, 40.00 mmol), triphenylmethanol (20.80 g, 80.00 mmol), Ac2O (7.50 mL, 80.00 mmol) and conc. H2SO4 was stirred in glacial acetic acid (120 mL), then rise to 50 °C. After 2 h the reaction mixture was poured into ice (800 g) resulting in a white precipitate. The precipitate was filtered off and redissolved in ethyl acetate (600 mL), washed with H2O (3 × 200 mL), dried over Na2SO4, and filtered and concentrated. A white solid 3(14.70 g, 70percent) was crystallization from ethyl acetate/petroleum ether.
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 35, p. 12998 - 13007
[2] Journal of Peptide Science, 2010, vol. 16, # 7, p. 364 - 374
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 15, p. 2786 - 2805
[4] Synthetic Communications, 2017, vol. 47, # 12, p. 1136 - 1141
[5] Tetrahedron Letters, 1991, vol. 32, # 6, p. 739 - 742
[6] Chemistry - A European Journal, 2009, vol. 15, # 1, p. 76 - 85
[7] Patent: US5324833, 1994, A,
  • 23
  • [ 76-84-6 ]
  • [ 71989-16-7 ]
  • [ 107-06-2 ]
  • [ 132388-59-1 ]
Reference: [1] Patent: US5324833, 1994, A,
  • 24
  • [ 76-84-6 ]
  • [ 132388-59-1 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 6, p. 739 - 742
[2] Tetrahedron Letters, 1991, vol. 32, # 6, p. 739 - 742
  • 25
  • [ 76-84-6 ]
  • [ 71989-20-3 ]
  • [ 132327-80-1 ]
Reference: [1] Patent: US5354843, 1994, A,
  • 26
  • [ 76-84-6 ]
  • [ 132327-80-1 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 6, p. 739 - 742
[2] Tetrahedron Letters, 1991, vol. 32, # 6, p. 739 - 742
  • 27
  • [ 2302-25-2 ]
  • [ 76-83-5 ]
  • [ 76-84-6 ]
  • [ 87941-55-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989, p. 95 - 99
  • 28
  • [ 76-84-6 ]
  • [ 27486-87-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1970, vol. 13, p. 414 - 418
  • 29
  • [ 76-84-6 ]
  • [ 139224-85-4 ]
  • [ 167015-23-8 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 43, p. 8743 - 8750
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