80442-95-1

Basic information

• Product Name: ethyl 5-thioxo-L-prolinate
• Synonyms: ethyl 5-thioxo-L-prolinate;L-Proline, 5-thioxo-, ethyl ester (9CI);(2S)-5-Thioxopyrrolidine-2α-carboxylic acid ethyl ester;5-Thioxo-L-proline ethyl ester;5-Thioxoproline ethyl ester;5-Thioxopyrrolidine-2α-carboxylic acid ethyl ester;Einecs 279-472-7
• CAS NO: 80442-95-1
• Molecular Formula: C₇H₁₁NO₂S
• Molecular Weight: 173.23274
• EINECS: 279-472-7
• Product Categories: PYRROLE
• Mol File: 80442-95-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 242.5°C at 760 mmHg
• Flash Point: 100.5°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 0.0338mmHg at 25°C
• Refractive Index: 1.542
• CAS DataBase Reference: ethyl 5-thioxo-L-prolinate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 5-thioxo-L-prolinate(80442-95-1)
• EPA Substance Registry System: ethyl 5-thioxo-L-prolinate(80442-95-1)

Safety Data

• Hazardous Substances Data: 80442-95-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H11NO2S/c1-2-10-7(9)5-3-4-6(11)8-5/h5H,2-4H2,1H3,(H,8,11)/t5-/m0/s1

Upstream product

• 7149-65-7 ethyl (S)-pyroglutamate 
• 56-86-0 L-glutamic acid 

Downstream Products

• 1621003-90-4 (S)-ethyl 5-(4,4-dimethyl-2,6-dioxocyclohexylidene)pyrrolidine-2-carboxylate 
• 1421277-03-3 (S)-ethyl 5-((2-oxo-2-phenylethyl)thio)-3,4-dihydro-2H-pyrrole-2-carboxylate 
• 1353674-41-5 (S)-dimethyl 2-(5-(ethoxycarbonyl)pyrrolidin-2-ylidene)malonate 
• 1353674-43-7 (S)-ethyl 5-((2-ethoxy-2-oxoethyl)thio)-3,4-dihydro-2H-pyrrole-2-carboxylate 
• 623-91-6 diethyl Fumarate 
• 468096-97-1 ethyl (3S,5aR)-tetrahydropyrrolo[1,2-b]oxaziridine-3-carboxylate 
• 468096-98-2 ethyl (3S,5aS)-tetrahydropyrrolo[1,2-b]oxaziridine-3-carboxylate 
• 172879-74-2 ethyl (S)-3,4-dihydro-2H-pyrrole-2-carboxylate 
• 908366-29-0 (2S,5S)-N-benzoyl-5-(1,1-di(ethoxycarbonyl)ethyl)-pyrrolidine-2-carboxylic acid ethyl ester 
• 908365-91-3 (2S,5S)-N-benzoyl-5-(di(ethoxycarbonyl)methyl)-pyrrolidine-2-carboxylic acid ethyl ester 
• 675588-13-3 (2S,5R)-N-benzoyl-5-(di(ethoxycarbonyl)methyl)-pyrrolidine-2-carboxylic acid ethyl ester 
• 142890-15-1 (S)-diethyl 2-(2-((tert-butyldiphenylsilyloxy)methyl)pyrrolidin-5-ylidene)malonate 

Relevant articles and documents

Concise enantiospecific synthesis of a coccinellied alkaloid, (-)-adalinine.

[reaction: see text] An enantiospecific synthesis of a coccinellied alkaloid, (-)-adalinine, was established starting from (S)-(-)-pyroglutamic acid, where a stereoselective Michael addition and a samarium iodide-promoted regioselective carbon-nitrogen bond cleavage reaction were involved as the key reactions.

2,5-Disubstituted pyrrolidines: Synthesis by enamine reduction and subsequent regioselective and diastereoselective alkylations

Methodology for the diastereoselective synthesis of 2,5-disubstituted pyrrolidines by reduction of enamines derived from pyroglutamic acid is reported; the nature of nitrogen protection was found to be critical for the stereochemical control of the reaction outcome. Regioselective manipulation of the C-2 and C-5 substituents is possible, providing access to differently substituted pyrrolidines for a limited number of cases. The Royal Society of Chemistry 2006.

Studies towards the total synthesis of batzelladine A

Application of a diastereoselective three-component coupling to the bicyclic core of the batzelladine alkaloids is described. The synthesis features the elaboration of glutamic acid by use of Eschenmoser sulfide contraction. An earlier approach is also included, which shows some limitations of dithiane chemistry when applied to the particular compounds required for this target.