31456-71-0

Basic information

• Product Name: (S)-4,5-DIDEHYDROPIPECOLIC ACID
• Synonyms: (S)-4,5-DIDEHYDROPIPECOLIC ACID;Zinc02578759;2-Pyridinecarboxylic acid, 1,2,3,6-tetrahydro-, (2S)-
• CAS NO: 31456-71-0
• Molecular Formula: C₆H₉NO₂
• Molecular Weight: 127.14
• Mol File: 31456-71-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 277.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.176±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 2.23±0.20(Predicted)
• CAS DataBase Reference: (S)-4,5-DIDEHYDROPIPECOLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4,5-DIDEHYDROPIPECOLIC ACID(31456-71-0)
• EPA Substance Registry System: (S)-4,5-DIDEHYDROPIPECOLIC ACID(31456-71-0)

Safety Data

• Hazardous Substances Data: 31456-71-0(Hazardous Substances Data)

Usage

General Description

(S)-4,5-DIDEHYDROPIPECOLIC ACID is a chemical compound that belongs to the class of organic compounds known as proline and derivatives. It is a derivative of proline, which is a nonessential amino acid that plays a crucial role in the structure and function of proteins. (S)-4,5-DIDEHYDROPIPECOLIC ACID is a chiral molecule, meaning it has a non-superimposable mirror image, and its configuration is specified by the prefix "S." (S)-4,5-DIDEHYDROPIPECOLIC ACID has potential pharmacological properties and may have applications in the fields of medicine and biochemistry. Its chemical structure and properties make it a subject of interest for further research and development in various areas of science and technology.

Upstream product

• 282527-09-7 methyl (S)-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate 
• 282527-06-4 methyl 2-[(1-benzyloxyallyl)-(4-nitrobenzenesulfonyl)amino]-(S)-pent-4-enoate 
• 282527-08-6 methyl (2S)-6-benzyloxy-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate 
• 305836-78-6 (2S)-1-(4-methylphenylsulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylic acid 
• 307304-57-0 (2S,4'S,5'R)-[(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)(1,3,4,6-tetrahydro-2-pyridinyl)]methanone 
• 141083-85-4 (S)-methyl 1,2,3,6-tetrahydropyridine-2-carboxylate 
• 919116-89-5 N-allyl-N-(1-benzyloxymethyl-3-hydroxy-propyl)-4-methyl-benzenesulfonamide 
• 919116-86-2 (2S)-N-allyl-N-(1-benzyloxymethyl-but-3-enyl)-4-methyl-benzenesulfonamide 
• 919116-87-3 (2S)-2-benzyloxymethyl-1-(4-methylphenylsulfonyl)-1,2,3,6-tetrahydropyridine 
• 919116-91-9 [1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-methanol 
• 919116-85-1 (2S)-N-allyl-N-[1-benzyloxymethyl-3-(t-butyldimethylsilanyloxy)propyl]-4-methylbenzenesulfonamide 
• 919116-90-8 N-allyl-N-(1-benzyloxymethyl-3-oxopropyl)-4-methylbenzenesulfonamide 

Downstream Products

• 417726-36-4 (S)-1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridine-2-carboxylic acid 
• 273921-32-7 (2S)-N-benzoyl-2-piperidinecarboxylic acid 
• 3105-95-1 pipecolinic acid 
• 76186-42-0 (S)-1-benzoyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid 

Relevant articles and documents

Synthesis of pipecolic acid and baikiain

A straightforward synthesis of pipecolic acid and baikiain was achieved from trans-(2S,4R)-4-hydroxyproline via the key steps of regioselective Baeyer-Villiger reaction. and ring-closing metathesis.

A ring-closing metathesis-mediated route to novel enantiopure conformationally restricted cyclic amino acids

A combination of palladium-catalysed N,O-acetal formation, ruthenium- catalysed ring-closing metathesis and N-sulfonyliminium ion-mediated C-C bond formation constitutes an efficient and versatile route to a set of enantiomerically pure 2,6-disubstituted unsaturated pipecolic acid derivatives.

Asymmetric synthesis of cyclic α-amino acids (-)-baikiain and (-)-4 methyleneproline from (S)-Boc-BMI

The enantiomerically pure glycine derivative tert-butyl (S)-2-(tert-butyl)-3-methyl-4-oxo-l-imidazolidinecarboxylate (Boc-BMI) reacts with (Z)-1,4-dichloro-2-butene and 3-chloro-2-(chloromethyl)-1-propene to give the bicyclic intermediates 5 and 6, respectively. These dialkylated systems are hydrolyzed to the corresponding heterocyclic a-amino acids (S)-baikiain (L-4,5-didehydropipecolic acid) and (S)-4-methylene proline which are obtained in 96 and 90% ee, respectively.