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[ CAS No. 20020-27-3 ] {[proInfo.proName]}

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Chemical Structure| 20020-27-3
Chemical Structure| 20020-27-3
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Product Details of [ 20020-27-3 ]

CAS No. :20020-27-3 MDL No. :MFCD01715258
Formula : C9H12O3S Boiling Point : -
Linear Structure Formula :- InChI Key :NCLPKLKVZDQOFW-UHFFFAOYSA-N
M.W : 200.26 Pubchem ID :146679
Synonyms :

Calculated chemistry of [ 20020-27-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.07
TPSA : 51.75 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) : -6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.01
Log Po/w (XLOGP3) : 1.6
Log Po/w (WLOGP) : 2.29
Log Po/w (MLOGP) : 1.83
Log Po/w (SILICOS-IT) : 1.33
Consensus Log Po/w : 1.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.17
Solubility : 1.36 mg/ml ; 0.00681 mol/l
Class : Soluble
Log S (Ali) : -2.3
Solubility : 1.01 mg/ml ; 0.00503 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.26
Solubility : 0.109 mg/ml ; 0.000545 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.19

Safety of [ 20020-27-3 ]

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 [ 20020-27-3 ]

* 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 [ 20020-27-3 ]
  • Downstream synthetic route of [ 20020-27-3 ]

[ 20020-27-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 60-12-8 ]
  • [ 124-63-0 ]
  • [ 20020-27-3 ]
YieldReaction ConditionsOperation in experiment
99% With triethylamine In dichloromethane at 0 - 20℃; for 3 h; Inert atmosphere General procedure: To a solution of corresponding alcohol (12A-B) or (15A-B) or (17A-B) or (19A-B) or (23A-B) (2.14 mmol) and triethylamine (0.36 mL, 2.59 mmol) in anhydrous dichloromethane (6 mL), kept to 0 °C, was added mesyl chloride (0.18 mL, 2.31 mmol). The reaction was maintained at 0 °C during the first hour, followed by warming to room temperature, under vigorous stirring and nitrogen atmosphere for 3 h. At the end of this time the solution was extracted with dichloromethane (3 .x. 30 mL) and the combined organic extracts were washed with a 10percent aqueous hydrochloric acid solution, brine, dried over sodium sulfate and evaporated. The obtained residue was separated by chromatography on silica gel eluted with dichloromethane, followed by chloroform to give the desired O-mesylated derivatives, as described in Supplementary Material.
76%
Stage #1: With triethylamine In tetrahydrofuran at 0℃;
Stage #2: at 0 - 20℃;
General procedure: To a flask that was charged with the benzyl alcohol (10 mmol), triethylamine (20 mmol) in THF (25 mL) cooled at 0 °C, was added mesyl chloride (20 mmol) in THF (50 mL) over half an hour. Then the mixture was allowed to stir at room temperature for about 20-30 min. Cold water was added to the mixture, then the mixture was extracted with diethyl ether (125 mLx1). Triethylamine (5 mol) was added into the crude product solution to remove the unreacted mesyl chloride. Then the solution was washed with saturated aqueous NaHCO3 (10 mL), cold water (25 mL) and brine (25 mL). The solution was dried over anhydrous Na2SO4. Removal of the solvent under reduced pressure gave the benzyl mesylate products, which are used in the coupling reaction without further purification.
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 3000 - 3012
[2] Synthetic Communications, 2011, vol. 41, # 5, p. 748 - 753
[3] Journal of Organic Chemistry, 1993, vol. 58, # 1, p. 272 - 274
[4] Tetrahedron, 2016, vol. 72, # 49, p. 8022 - 8030
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 10, p. 2807 - 2813
[6] Journal of Medicinal Chemistry, 1983, vol. 26, # 1, p. 42 - 50
[7] Journal of Chemical Research, Miniprint, 2000, # 6, p. 701 - 715
[8] Journal of the American Chemical Society, 2014, vol. 136, # 38, p. 13126 - 13129
[9] Patent: US9255101, 2016, B2, . Location in patent: Page/Page column 54
[10] Chemistry - An Asian Journal, 2018, vol. 13, # 3, p. 255 - 260
[11] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3145 - 3157
  • 2
  • [ 122-78-1 ]
  • [ 20020-27-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3145 - 3157
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