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[ CAS No. 81015-49-8 ] {[proInfo.proName]}

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Chemical Structure| 81015-49-8
Chemical Structure| 81015-49-8
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Product Details of [ 81015-49-8 ]

CAS No. :81015-49-8 MDL No. :MFCD07368615
Formula : C9H7NOS Boiling Point : -
Linear Structure Formula :- InChI Key :PXNRJZLHXKIISI-UHFFFAOYSA-N
M.W : 177.22 Pubchem ID :223840
Synonyms :

Calculated chemistry of [ 81015-49-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.57
TPSA : 61.36 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) : -5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 2.41
Log Po/w (WLOGP) : 2.52
Log Po/w (MLOGP) : 1.19
Log Po/w (SILICOS-IT) : 3.22
Consensus Log Po/w : 2.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.07
Solubility : 0.151 mg/ml ; 0.000852 mol/l
Class : Soluble
Log S (Ali) : -3.34
Solubility : 0.0809 mg/ml ; 0.000456 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.23
Solubility : 0.104 mg/ml ; 0.000585 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.94

Safety of [ 81015-49-8 ]

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 [ 81015-49-8 ]

* 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 [ 81015-49-8 ]
  • Downstream synthetic route of [ 81015-49-8 ]

[ 81015-49-8 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 27088-84-2 ]
  • [ 81015-49-8 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With boron tribromide In dichloromethane at -78 - 20℃; for 17 h;
Stage #2: With water In dichloromethane
Step 2; 4-Thiazol-2-yl-phenol; To a solution of the product of step 1 (1.0 g, 5.23 mmol) in methylene chloride (25 ml) was slowly added boron tribromide (2.00 ml, 15.7 mmol) at -78° C., and stirred at -78° C. for 1 h. After it was stirred at room temperature for 16 h, the reaction mixture was poured into ice-water. The product was collected on a filter, washed with ether to yield the title product (0.84 g, 84percent); 1H NMR (400 MHz, CDCl3) δ 7.85 (d, J=3.2 Hz, 1H), 7.79 (d, J=8.8 Hz, 2H), 7.67 (d, J=3.2 Hz, 1H), 6.88 (d, J=8.8 Hz, 2H); MS (ESI-) 176 (M-1, 100).
84%
Stage #1: With boron tribromide In dichloromethane at -78 - 20℃; for 17 h;
Stage #2: With water In dichloromethane at 0℃;
To a solution of the product from step 2 (1.0 g, 5.23 mmol) in methylene chloride (25 ml) was slowly added boron tribromide (2.00 ml, 15.7 mmol) at -78° C., and stirred at -78° C. for 1 h.
After it was stirred at room temperature for 16 h, the reaction mixture was poured into ice-water.
The product was collected on a filter, washed with ether to yield the product from step two (0.84 g, 84percent).
1H-NMR (400 MHz, CDCl3) δ 6.88 (d, J=8.8 Hz, 2H), 7.67 (d, J=3.2 Hz, 1H), 7.79 (d, J=8.8 Hz, 2H), 7.85 (d, J=3.2 Hz, 1H), MS (ESI-) m/z 176 (M-1).
0.42 g at 115℃; for 20 h; Step 2:
preparation of 4-(thiazol-2-yl)phenol
To a 100mL single-neck flask were added the product obtained from Step 1(0.9g, 4.7mmol) and 40percentHBr.
The product from Step 1 was completely dissolved, and the resulting solution was yellow transparent.
6mL acetic acid was added, and the solution was heated to 115°C and reacted for 20 hours.
The reaction was stopped after the starting materials almost disappeared.
The mixture was concentrated to dryness and separated by silica gel column chromatography to give 0.42g of a pale yellow solid.
1HNMR(300MHz,CDCl3)δ:7.83-7.88(m,3H,Ar-H),7.30(d,1H,Ar-H),6.92(d,2H,A r-H).
ESI-MS m/z: [M+H]+ =178.2.
Reference: [1] European Journal of Medicinal Chemistry, 2010, vol. 45, # 6, p. 2299 - 2306
[2] Patent: US2007/66820, 2007, A1, . Location in patent: Page/Page column 78
[3] Patent: US2008/33024, 2008, A1, . Location in patent: Page/Page column 7; 16
[4] Journal of Medicinal Chemistry, 1986, vol. 29, # 6, p. 1065 - 1080
[5] Journal of the American Chemical Society, 1930, vol. 52, p. 1585
[6] Patent: US1970656, 1931, ,
[7] Bioorganic and medicinal chemistry, 2003, vol. 11, # 7, p. 1235 - 1246
[8] Patent: US5977105, 1999, A,
[9] Patent: EP2940031, 2015, A1, . Location in patent: Paragraph 0084
  • 2
  • [ 25984-63-8 ]
  • [ 7252-83-7 ]
  • [ 81015-49-8 ]
YieldReaction ConditionsOperation in experiment
60% With toluene-4-sulfonic acid In ethanol at 20 - 90℃; for 24 h; To a mixture of 4-hydroxybenzothioamide (30.64 g, 0.20 mol) and 2-bromo-l,l-dimethoxyethane (31.00 g, 0.20 mol) in EtOH (600 mL) was added 4-methylbenzenesulfonic acid (34.44 g, 0.20 mol) with stirring at rt. The reaction mixture was heated at 90 °C for 24 h, then cooled to rt and concentrated in vacuo. The mixture was diluted with H20 (200 mL), adjusted to pH 10 with saturated NaHC03aqueous solution and extracted with DCM (200 mL x 3). The combined organic phases were concentrated in vacuo to give the title compound as s yellow solid (21.3 g, 60percent).
60% With toluene-4-sulfonic acid In ethanol at 20 - 90℃; for 24 h; To a mixture of 4-hydroxybenzothioamide (30.64 g, 0.20 mol) and 2-bromo-1,1-dimethoxyethane (31.00 g, 0.20 mol) in EtOH (600 mL) was added 4-methylbenzenesulfonic acid (34.44 g, 0.20 mol) with stirring at rt.
The reaction mixture was heated at 90° C. for 24 h, then cooled to rt and concentrated in vacuo.
The mixture was diluted with H2O (200 mL), adjusted to pH 10 with saturated NaHCO3 aqueous solution and extracted with DCM (200 mL*3).
The combined organic phases were concentrated in vacuo to give the title compound as s yellow solid (21.3 g, 60percent).
60% With toluene-4-sulfonic acid In ethanol at 20 - 90℃; for 24 h; 4-hydroxythiobenzamide (30.64 g, 0.20 mol) and 2-bromo-1,1-dimethoxyethane (31.00 g, 0.20 mol) were stirred in ethanol (600 mL) at room temperature.P-toluenesulfonic acid (34.44 g, 0.20 mol) was added to the reaction solution.Heat to 90°C for 24 hours.After the reaction was completed, it was cooled to room temperature, the solvent was distilled off under reduced pressure, water (200 mL) was added, and the pH was adjusted to 8 with saturated sodium bicarbonate solution.Dichloromethane (200 mL x 3) was extracted and the organic phases were combined and concentrated by evaporation under reduced pressure to give a yellow solid (21.3 g, 60percent).
Reference: [1] Patent: WO2014/12360, 2014, A1, . Location in patent: Paragraph 00266
[2] Patent: US2015/87639, 2015, A1, . Location in patent: Paragraph 0511
[3] Patent: TWI607995, 2017, B, . Location in patent: Page/Page column 122
[4] Patent: CN108658937, 2018, A, . Location in patent: Paragraph 0175
  • 3
  • [ 3034-53-5 ]
  • [ 540-38-5 ]
  • [ 81015-49-8 ]
Reference: [1] Synthesis, 2001, # 1, p. 128 - 134
  • 4
  • [ 2362-64-3 ]
  • [ 81015-49-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 6, p. 1065 - 1080
[2] Journal of the American Chemical Society, 1930, vol. 52, p. 1585
[3] Patent: US1970656, 1931, ,
  • 5
  • [ 874-90-8 ]
  • [ 81015-49-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 6, p. 1065 - 1080
  • 6
  • [ 5720-07-0 ]
  • [ 81015-49-8 ]
Reference: [1] Patent: EP2940031, 2015, A1,
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