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[ CAS No. 925-47-3 ] {[proInfo.proName]}

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Chemical Structure| 925-47-3
Chemical Structure| 925-47-3
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Product Details of [ 925-47-3 ]

CAS No. :925-47-3 MDL No. :MFCD00087932
Formula : C8H14O4S Boiling Point : -
Linear Structure Formula :- InChI Key :TVCSSJHLVLMADJ-UHFFFAOYSA-N
M.W : 206.26 Pubchem ID :70216
Synonyms :

Calculated chemistry of [ 925-47-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 8
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.73
TPSA : 77.9 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.44
Log Po/w (XLOGP3) : 1.45
Log Po/w (WLOGP) : 0.85
Log Po/w (MLOGP) : 0.93
Log Po/w (SILICOS-IT) : 1.36
Consensus Log Po/w : 1.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.5
Solubility : 6.46 mg/ml ; 0.0313 mol/l
Class : Very soluble
Log S (Ali) : -2.69
Solubility : 0.419 mg/ml ; 0.00203 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.77
Solubility : 3.51 mg/ml ; 0.017 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.05

Safety of [ 925-47-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 925-47-3 ]

* 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 [ 925-47-3 ]
  • Downstream synthetic route of [ 925-47-3 ]

[ 925-47-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 925-47-3 ]
  • [ 95-92-1 ]
  • [ 1822-66-8 ]
YieldReaction ConditionsOperation in experiment
76.9% With sodium ethanolate In ethanol at 68℃; for 1 h; Microwave irradiation General procedure: Example B1
10.3 g of Example A6's product and 10.96 g of diethyl oxylate (Acros, Belgime) were mixed and then put in water bath at a temperature of 0 - 10°C. Sodium ethoxide (Acros, Belgime) in ethanol solution was dropwise added to the mixture and sufficiently stirred the solution.
The solution was then moved into a microwave reactor and heated by a 2.45 GHz microwave of a power of 100 W for 60 minutes.
The reaction temperature was maintained at 68°C.
Next, the solution was added with HCl (Scharlau, Australia) to adjust pH value to 7.0 - 7.5 in order to stop the reaction, and then evaporated to remove ethanol.
The dried mixture was added with HCl to adjust pH value to 2.5 - 3.0 and then added with 400 mL of deionized water to precipitate product.
After filtering, the obtained product was dried in an oven to obtain 8.58 g product of 2,5-diethoxycarbonyl-3,4-dihydroxythiophene.
The yield was 65.3percent.
60% With sodium ethanolate In ethanol at 0℃; Heating / reflux 2) Synthesis of diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate; [0080] In a 2 L two-necked flask equipped with a reflux condenser 175 g (2.57 mol) of sodium ethoxide was dissolved in 1200 mL anhydrous ethanol The reaction was cooled to 0 C and a solution of 106 g (0.514 mol) diethylthioglycolate and 188 g (1.28 mol) diethyl oxalate in ethanol was added dropwise. Upon completion of the addition, the cooling bath was removed and the reaction heated to reflux overnight. The reaction was then cooled to room temperature and filtered The resulting yellow solid was washed with ethanol and allowed to dry. The solid was split into two portions and each was added to a large Erlenmeyer flask with water to make a suspension upon stirring. Acidification with HCl provided a white solid. The solid was filtered and allowed to dry under vacuum to give 80g (60percent yield) of product as a white powder. Further mateπal can be isolated by cooling the mother liquor and subsequent filtration. Structure and puπty were confirmed by Η/13C NMR and LC-MS.
44.9 g
Stage #1: With sodium ethanolate In ethanol at 5℃; for 2 h; Inert atmosphere; Reflux
Stage #2: With hydrogenchloride In water at 5 - 10℃; Inert atmosphere
In a 1-liter four-necked flask, 82.8 g (0.24 mol) of 20percent sodium ethoxide (Wako Pure Chemical Industries, reagent grade 1) was charged under a nitrogen atmosphere and cooled to 5 ° C. To this, a solution obtained by adding 20.6 g (0.10 mol) of diethyl thioglycolate obtained in a) and 17.2 g (0.12 mol) of diethyl oxalate (manufactured by Wako Pure Chemical Industries, special grade) to ethanol 18.8 g was added dropwise over 1 hour. Further, the mixture was heated under reflux for 1.0 hour. After the completion of the reaction, the reaction solution was concentrated at 60 ° C/16 to 20 mmHg, and 515.2 g of water was added, cooled to 5 ° C, and 38.1 g (0.37 mol) of 35percent hydrochloric acid was added dropwise at 5 to 10 ° C to obtain a white precipitate. The obtained precipitate was filtered, dispersed in water, washed and filtered, and then dried at 60 ° C/1 mmHg for 4 hours to obtain 23.8 g of a white powder. In the same manner, 44.9 g of a white powder was obtained. These powders were single peaks by gas chromatography analysis and when 1 H-NMR and 13 C-NMR were measured, it was confirmed that they were 3,4-dihydroxy-2,5-dicarboxylic acid thiophene diethyl ester.
Reference: [1] RSC Advances, 2015, vol. 5, # 4, p. 2630 - 2639
[2] Patent: EP2548875, 2013, A1, . Location in patent: Paragraph 0074-0082
[3] Acta Crystallographica Section C: Crystal Structure Communications, 2004, vol. 60, # 5, p. o338-o340
[4] Journal of Materials Chemistry, 2005, vol. 15, # 45, p. 4783 - 4792
[5] Patent: WO2006/73968, 2006, A2, . Location in patent: Page/Page column 22
[6] Chemische Berichte, 1910, vol. 43, p. 902[7] Chemische Berichte, 1915, vol. 48, p. 1612
[8] Journal de Chimie Physique et de Physico-Chimie Biologique, 1998, vol. 95, # 6, p. 1258 - 1261
[9] European Journal of Medicinal Chemistry, 2009, vol. 44, # 9, p. 3672 - 3679
[10] European Journal of Medicinal Chemistry, 2009, vol. 44, # 11, p. 4376 - 4384
[11] Chemical Communications, 2009, # 46, p. 7203 - 7205
[12] RSC Advances, 2015, vol. 5, # 97, p. 79800 - 79806
[13] Patent: JP5998836, 2016, B2, . Location in patent: Paragraph 0059; 0061
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