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[ CAS No. 146796-02-3 ] {[proInfo.proName]}

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Chemical Structure| 146796-02-3
Chemical Structure| 146796-02-3
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Product Details of [ 146796-02-3 ]

CAS No. :146796-02-3 MDL No. :MFCD11045357
Formula : C7H8O3S Boiling Point : -
Linear Structure Formula :- InChI Key :YFCHAINVYLQVBG-UHFFFAOYSA-N
M.W : 172.20 Pubchem ID :16067438
Synonyms :

Calculated chemistry of [ 146796-02-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.43
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.16
TPSA : 66.93 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 0.7
Log Po/w (WLOGP) : 0.88
Log Po/w (MLOGP) : -0.08
Log Po/w (SILICOS-IT) : 2.27
Consensus Log Po/w : 1.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.62
Solubility : 4.14 mg/ml ; 0.024 mol/l
Class : Very soluble
Log S (Ali) : -1.68
Solubility : 3.57 mg/ml ; 0.0207 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.29
Solubility : 8.77 mg/ml ; 0.0509 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.29

Safety of [ 146796-02-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 146796-02-3 ]

* 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 [ 146796-02-3 ]
  • Downstream synthetic route of [ 146796-02-3 ]

[ 146796-02-3 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 146796-14-7 ]
  • [ 146796-02-3 ]
YieldReaction ConditionsOperation in experiment
99.4% With copper(II) oxide In N,N-dimethyl-formamide at 130 - 132℃; for 8 h; Inert atmosphere Using the obtained 2-hydroxymethyl-2,3-dihydro-thieno [3,4-b] [1,4] dioxin-5,7- dicarboxylic acid, 2-hydroxymethyl-2 , 3-dihydro-thieno [3,4-b] [1,4] dioxine was synthesized.A stirrer, a thermometer,Into a 5-liter four-neck separable flask equipped with a condenser tube,Under nitrogen atmosphere, 135.9 g of 2-hydroxymethyl-2,3-dihydro-thieno [3,4-b] [1,4] dioxine-5,7- dicarboxylic acid obtained by the above reaction 8.3 g (0.10 mol) of copper (II) oxide and 2700.0 g of N, N-dimethylformamide were charged into a reactor equipped with a stirrer and a reflux condenser, and heating and stirring was continued for 8 hours at a temperature range of 130 to 132 ° C. After completion of the reaction, analysis by liquid chromatography revealed that the peak of 2-hydroxymethyl-2,3-dihydro-thieno [3,4-b] [1,4] dioxine-5,7-dicarboxylic acid disappeared It was. Further, when the reaction solution was subjected to gas chromatography analysis, a main peak was observed. The reaction solution was concentrated and cooled to 25 ° C. or lower,It was dissolved in 1100 ml of toluene, filtered, washed with 1percent aqueous hydrochloric acid and saturated brine, and concentrated. The concentration was purified by column chromatography, and after drying, 76.0 g of a pale yellow solid was obtained. As a result of 1 H-NMR, 13 C-NMR, and GC-MS measurement, the obtained compound had a main component of 99.4percent as determined by gas chromatography analysis. As a result, 2-hydroxymethyl-2, 3-dihydro-thieno [3,4-b] [1,4] dioxine was obtained.
96.8% With copper(II) oxide In N,N-dimethyl-formamide at 139℃; for 20 h; Inert atmosphere Into a 300 ml three-necked flask equipped with a stirrer, a thermometer, and a cooling tube, a nitrogen atmosphere , 2-hydroxymethyl-2,3-dihydro-thieno [3, 4 -b] [1,4] dioxine-5,7-dicarboxylic acid obtained in the reaction of b (estimated pure 50.0 mmol), 0.8 g of copper (II) oxide was added, 262.1 g of N, N-dimethylformamide was charged After raising the temperature to 139 ° C., heating and stirring was continued for 20 hours. Analysis by liquid chromatography after completion of the reaction revealed that the peak of 2-hydroxymethyl-2,3-dihydro-thieno [3,4-b] [1,4] dioxin-5,7-dicarboxylic acid dimethyl ester disappeared . Further, when the reaction solution was analyzed by gas chromatography, a single peak was observed. The reaction solution was concentrated, After cooling to 25 ° C. or lower, 200 ml of ethyl acetate and 100 ml of saturated brine were added and the mixture was once filtered. After liquid separation, the solution re-extracted with ethyl acetate from the aqueous layer was combined with the previous extract and concentrated. The concentrate was purified by column chromatography to obtain 9.0 g of a pale yellow solid. As a result of 1 H-NMR, 13 C-NMR, and GC-MS measurement, the obtained compound had a main component of 96.8percent as determined by gas chromatography analysis, and as a result, 2-hydroxymethyl-2,3- Dihydro-thieno [3,4-b] [1,4] dioxine was confirmed.
96.4% at 150℃; for 3 h; S3: 2-hydroxymethyl-2,3-dihydrothieno[3,4-b]-[1,4]-dioxin-5,7-dicarboxylic acid prepared by S2 and a molar ratio of 9.6 g is 1:2 of chromium and copper nitrate mixed catalyst addedIn 535 g of N-methylpyrrolidone, the reaction was heated at a temperature of 150 ° C for 3 hours.Under reduced pressure, 91.0 g of hydroxymethyl EDOT was obtained, and the content was 97.7percent by gas chromatography, and the yield was 96.4percent.
48% With copper(II) oxide In quinoline at 225℃; 5) Synthesis of diethyl-2-(hydroxymethyl)-2,3-dihydrothieno[3,4-]-l,4-dioxin- 2-yl methanol; [0083] In a 100 mL round bottom flask, 14.0 g (0.053 mol) of finely powdered 2,3-dihydro-2-(hydroxymethyl)thieno[3,4-fr]dioxine-5.7-dicarboxylic acid, 0.42 g copper(II) oxide, and 25 mL quinoline were combined. A reflux condenser was equipped and reaction flask purged with nitrogen. The mixture was heated to 225 C and the reaction tracced by TLC. Once all starting material was consumed, the reaction was cooled to room temperature, diluted with ether and filtered. The ether was removed under reduced pressure. The crude product mixture was purified by column chromatography using 30percent ethyl acetate in hexane. Upon removal of the solvent 4.4 g (48percent yield) of a light yellow oil was isolated. Structure and purity were confirmed by Η/I3C NMR and GC-MS.

Reference: [1] Patent: JP2015/182973, 2015, A, . Location in patent: Paragraph 0113; 0115; 0116
[2] Patent: JP2015/67606, 2015, A, . Location in patent: Paragraph 0072
[3] Patent: CN108329329, 2018, A, . Location in patent: Paragraph 0072; 0029; 0033; 0036; 0040; 0043; 0047
[4] Journal de Chimie Physique et de Physico-Chimie Biologique, 1998, vol. 95, # 6, p. 1258 - 1261
[5] Patent: WO2006/73968, 2006, A2, . Location in patent: Page/Page column 23
[6] Chemical Communications, 2009, # 46, p. 7203 - 7205
[7] Patent: US7147936, 2006, B2, . Location in patent: Page/Page column 29-30
[8] Patent: US2004/44214, 2004, A1, . Location in patent: Page 10
  • 2
  • [ 51792-34-8 ]
  • [ 56-81-5 ]
  • [ 146796-02-3 ]
YieldReaction ConditionsOperation in experiment
55% With toluene-4-sulfonic acid; hydroquinone In diethylene glycol dimethyl ether at 140℃; for 10 h; Inert atmosphere 152 g (1.05 mol) of 3,4-dimethoxythiophene, 775 g (8.42 mol) of glycerin, 19.9 g (0.105 mol) of p-toluenesulfonic acid monohydrate, 11.5 g (0.105 mol ) of Hydroquinone and 3.68 L of diglyme were added to a reactor, and then the inside of the reaction system was sufficiently purged with argon gas. The oxygen concentration in the reaction vessel gas atmosphere was 0.3 vol percent. Thereafter, the mixture was heated to 140 ° C and stirred for 10 hours. After cooling to room temperature, the reaction solution was analyzed by gas chromatography and the formation rate of the target product (2) was 75percent and the formation rate of the by-product (4) was 0.5percent (molar ratio 99.3 : 0.7). 1.68 L of a 10percent sodium hydroxide aqueous solution was added and the mixture was allowed to stand for 12 hours. The solvent was distilled off and extracted three times with a toluene / saturated aqueous sodium chloride solution. The toluene layer was concentrated and dried and dissolved in 3.7 L of a mixed solvent of toluene / ethyl acetate = 4/1, and the insoluble matter was filtered off. The solvent was distilled off and dissolved in 220 g of toluene, then 220 g of hexane was further added, and the mixture was allowed to stand at about 10 ° C for 2 hours. The obtained crystals were filtered, then washed with hexane and dried under vacuum to obtain 100 g of the desired product (2) as a white precipitate (yield: 55percent). By gas chromatography, 0.5percent of the by-product (4) was contaminated, and the purity of the target product (2) was 99.5percent.
Reference: [1] Patent: JP2018/65778, 2018, A, . Location in patent: Paragraph 0044-0081
  • 3
  • [ 897922-08-6 ]
  • [ 146796-02-3 ]
YieldReaction ConditionsOperation in experiment
85% Heating / reflux 2) Synthesis of (2,3-dihydrothieno[3,4-b][l,4]dioxin-3-yl)methanol:; [0090] In a 100 mL round bottom flask, 7.5 g (0.027 mol) (2,3- dihydrothieno[3,4-b][l,4]dioxin-3-yl)methyl benzoate was dissolved in a minimal amount of warm ethanol and dropwise added to a refluxing solution of 4.58 g (0.081 mol) potassium hydroxide in 50 mL water. After heating overnight, the reaction was cooled to room temperature and acidified to pH 7 by dropwise addition of concentrated hydrochloric acid. The reaction mixture was extracted EPO <DP n="29"/>with methylene chloride. The organic fractions were combined and the solvent removed under reduced pressure. Purification by column chromatography provided 3.95 g (85percent yield) of (2,3-dihydrothieno[3,4-b][l,4]dioxin-3- yl)methanol. Structure was confirmed by 1H/13C NMR and LC-MS.
85% With hydrogenchloride; potassium hydroxide In ethanol; water In a 100 mL round bottom flask, 7.5 g (0.027 mol) of (2,3-dihydrothieno[3,4-b][1,4]dioxin-3-yl)methyl benzoate was dissolved in a minimal amount of warm ethanol and dropwise added to a refluxing solution of 4.58 g (0.081 mol) of potassium hydroxide in 50 mL water.
After heating overnight, the reaction was cooled to room temperature and acidified to pH 7 by dropwise addition of concentrated hydrochloric acid.
The reaction mixture was extracted with methylene chloride.
The organic fractions were combined and the solvent removed under reduced pressure.
Purification by column chromatography provided 3.95 g (85percent yield) of (2,3-dihydrothieno[3,4-b][1,4]dioxin-3-yl)methanol.
Structure was confirmed by 1H/13C NMR and LC-MS.
Reference: [1] Patent: WO2006/73968, 2006, A2, . Location in patent: Page/Page column 27-28
[2] Patent: US2008/166564, 2008, A1,
  • 4
  • [ 897922-07-5 ]
  • [ 146796-02-3 ]
YieldReaction ConditionsOperation in experiment
90% Heating / reflux 2) Synthesis of (2,3-dihydrothieno[3,4-.pound.][l,4]dioxin-3-yl)methanol (EDOT- MeOH); [0088] In a 25 mL round bottom flask equipped with a reflux condenser 0.64 g (0.0030 mol) of (2,3-dihydrothieno[3,4-b][l,4]dioxin-2-yl)methyl acetate was combined with 50percent NaOH in water. The reaction was refluxed overnight and then cooled to room temperature. It was then poured into an Erlenmeyer flask filled with 100 mL water. The mixture was acidified then extracted with DCM. The solvent was removed under reduced pressure and column chromatography (7:3 hexanes/ethyl acetate) was performed to give 0.46 g (90percent) of product. The structure was confirmed by LC-MS and Η/13C NMR.
Reference: [1] Patent: WO2006/73968, 2006, A2, . Location in patent: Page/Page column 26
[2] Journal of Polymer Science, Part A: Polymer Chemistry, 2014, vol. 52, # 14, p. 1989 - 1999
[3] Chinese Chemical Letters, 2014, vol. 25, # 4, p. 517 - 522
  • 5
  • [ 58416-04-9 ]
  • [ 3132-64-7 ]
  • [ 146796-02-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2015, vol. 51, # 5, p. 1277 - 1281
  • 6
  • [ 204444-02-0 ]
  • [ 146796-02-3 ]
Reference: [1] Journal de Chimie Physique et de Physico-Chimie Biologique, 1998, vol. 95, # 6, p. 1258 - 1261
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