20462-00-4 Usage
Description
Ethyl 1,3-dithiane-2-carboxylate is an α-keto acid equivalent and a bulky equivalent of acetate, characterized by its clear yellowish liquid appearance. It is known for its participation in syn-selective aldol reactions and its ability to undergo asymmetric oxidation, leading to the formation of trans bis-sulfoxide. Ethyl 1,3-dithiane-2-carboxylate can also be used to generate carbanion, which is utilized in the preparation of α-keto esters.
Uses
Used in Organic Synthesis:
Ethyl 1,3-dithiane-2-carboxylate is used as a reagent in organic synthesis for its ability to participate in syn-selective aldol reactions. This makes it a valuable tool for creating complex molecular structures with specific stereochemistry.
Used in Asymmetric Oxidation:
The compound is used as a substrate in asymmetric oxidation reactions, which can produce trans bis-sulfoxide with a yield of up to 60%. This application is particularly relevant in the field of pharmaceuticals and materials science, where the control of stereochemistry is crucial for the development of effective and selective compounds.
Used in the Preparation of α-Keto Esters:
Ethyl 1,3-dithiane-2-carboxylate is used as a precursor to generate carbanion, which finds application in the preparation of α-keto esters. These esters are important intermediates in the synthesis of various organic compounds, including pharmaceuticals and natural products.
Used in the Pharmaceutical Industry:
Ethyl 1,3-dithiane-2-carboxylate is used as a key intermediate in the synthesis of certain pharmaceutical compounds. Its ability to participate in selective reactions and generate specific intermediates makes it a valuable asset in the development of new drugs and therapies.
Used in the Chemical Research Industry:
In the field of chemical research, Ethyl 1,3-dithiane-2-carboxylate is used as a model compound to study reaction mechanisms and develop new synthetic methodologies. Its unique reactivity and properties allow researchers to explore novel approaches to organic synthesis and expand the scope of chemical reactions.
Synthesis Reference(s)
Synthetic Communications, 11, p. 343, 1981 DOI: 10.1080/00397918108063615
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.
