20309-87-9

Basic information

• Product Name: 4-methyleneproline
• Synonyms: 4-methyleneproline;(S)-4-methylenepyrrolidine-2-carboxylic acid
• CAS NO: 20309-87-9
• Molecular Formula: C₆H₉NO₂
• Molecular Weight: 127.1412
• Mol File: 20309-87-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 269.2 °C at 760 mmHg
• Flash Point: 116.6 °C
• Appearance: /
• Density: 1.18 g/cm³
• Vapor Pressure: 0.00209mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: 4-methyleneproline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyleneproline(20309-87-9)
• EPA Substance Registry System: 4-methyleneproline(20309-87-9)

Safety Data

• Hazardous Substances Data: 20309-87-9(Hazardous Substances Data)

Usage

General Description

4-methyleneproline is an organic compound and a derivative of the amino acid proline. It is commonly used in organic synthesis and pharmaceutical research due to its unique chemical and structural properties. The addition of a methylene group in the proline molecule enhances its reactivity, making it a valuable building block for the synthesis of complex molecules. This chemical modification also alters the conformation and stability of proline-containing peptides, providing novel opportunities for drug design and development. In addition, 4-methyleneproline has been investigated for its potential application in the synthesis of bioactive natural products and pharmaceuticals. Overall, this compound offers a promising platform for the development of new drugs and biologically active molecules.

InChI:InChI=1/C6H9NO2/c1-4-2-5(6(8)9)7-3-4/h5,7H,1-3H2,(H,8,9)/t5-/m0/s1

Upstream product

• 84348-38-9 (S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid 
• 144422-81-1 N-phenylsulphonyl-4-exomethylene-(S)-proline benzylester 
• 159830-01-0 (S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester 
• 113400-36-5 benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate 
• 144422-80-0 N-phenylsulphonyl-N-propargyl-3-bromo-(S)-alanine benzylester 
• 144423-03-0 N-phenylsulphonyl-N-propargyl-O-tetrahydropyranyl-(S)-serine benzylester 
• 84348-39-0 (S)-1-tert-butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate 

Downstream Products

• 84348-38-9 (S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid 
• 144422-82-2 N-Boc-4-exomethylene-(S)-prolinyl dibenzyl-(S)-aspartate 

Relevant articles and documents

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.

Syntheses of proline analogues as potential mechanism-based inhibitors of proline dehydrogenase: 4-methylene-L-, (E)- and (Z)-4-(fluoromethylene)-L-, cis- and trans-5-ethynyl-(±)-, and cis- and trans-5-vinyl-L-proline

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