20462-00-4 Usage
Chemical Properties
clear yellowish liquid
Uses
Ethyl 1,3-dithiane-2-carboxylate is used in syn-selective aldol reactions. It undergoes asymmetric oxidation to give trans bis-sulfoxide. It is used to generate carbanon, which finds application in the preparation of alfa- keto esters.
Synthesis Reference(s)
Synthetic Communications, 11, p. 343, 1981 DOI: 10.1080/00397918108063615
General Description
Ethyl 1,3-dithiane-2-carboxylate is an α-keto acid equivalent and bulky equivalent of acetate. It participates in syn-selective aldol reactions. It can be prepared from the reaction of ethyl diethoxyacetate and 1,3-propanedithiol in the presence of BF3/Et2O. Asymmetric oxidation of ethyl 1,3-dithiane-2-carboxylate by Modena protocol has been reported to afford trans bis-sulfoxide in 60% yield. Carbanion from ethyl 1,3-dithiane-2-carboxylate may be employed for the preparation of α-keto esters.
Purification Methods
Dissolve the ester in CHCl3, wash with aqueous K2CO3, twice with H2O, dry over MgSO4, filter, evaporate and distil the residue. [Eliel & Hartman J Org Chem 37 505 1972, Seebach Synthesis 1 17 1969, Beilstein 19/7 V 227.]
Check Digit Verification of cas no
The CAS Registry Mumber 20462-00-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,4,6 and 2 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 20462-00:
(7*2)+(6*0)+(5*4)+(4*6)+(3*2)+(2*0)+(1*0)=64
64 % 10 = 4
So 20462-00-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3
20462-00-4Relevant articles and documents
A new synthesis of 2-substituted-1,3-dithianes from trichloromethyl compounds
Rivera, Nancy González,Becerril, David Corona,Guadarrama-Pérez, Carlos,Covarrubias-Zu?iga, Adrian,Avila-Zárraga, José Gustavo,Romero-Ortega, Moisés
, p. 1201 - 1204 (2007)
Trichloromethyl compounds are efficiently converted into 1,3-dithianes upon reaction with a disodium 1,3-propanedithiolate-1,3-propanedithiol mixture in DMF solution at 0 °C. This synthesis is limited to those substrates where the substituent attached to the trichloromethyl group is an electron-withdrawing group.
PYRIDAZINONE COMPOUNDS
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Page/Page column 86-87, (2008/12/07)
The invention is directed to pyridazinone compounds and pharmaceutical compositions containing such compounds that are useful in treating infections by hepatitis C virus.
Synthesis of α-difluoro and α-difluoro-β-trifluoroketo-derivatives as potential inhibitors for cholesterol ester hydrolase
David, Beatrice,Schuber, Francis
, p. 1673 - 1676 (2007/10/03)
Pancreatic Cholesterol Ester Hydrolase, a serine esterase, catalyzes the hydrolysis of cholesteryl esters in the gut. We report the convergent synthesis of α-difluoro-β-trifluoroketo-(5,10,15) and of α-difluoroketo-derivatives (22,23) as inhibitors of this enzyme that were designed to generate stable tetrahedral reaction intermediates.
