39647-11-5

Basic information

• Product Name: methyldihydroepijasmonate,(+)-methyldihydroepijasmonate
• Synonyms: methyldihydroepijasmonate,(+)-methyldihydroepijasmonate;(+)-(1R,2S)-Form;(+)-methyl dihydroepijasmonate
• CAS NO: 39647-11-5
• Molecular Formula: C₁₃H₂₂O₃
• Molecular Weight: 226.31198
• Mol File: 39647-11-5.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• CAS DataBase Reference: methyldihydroepijasmonate,(+)-methyldihydroepijasmonate(CAS DataBase Reference)
• NIST Chemistry Reference: methyldihydroepijasmonate,(+)-methyldihydroepijasmonate(39647-11-5)
• EPA Substance Registry System: methyldihydroepijasmonate,(+)-methyldihydroepijasmonate(39647-11-5)

Safety Data

• Hazardous Substances Data: 39647-11-5(Hazardous Substances Data)

Upstream product

• 120-92-3 cyclopentanone 
• 110-62-3 pentanal 
• 16424-35-4 2-pentylidenecyclopentan-1-one 
• 82423-74-3 3-methoxycarbonylmethyl-2-(1-phenylthiopentyl)cyclopentanone 
• 155016-14-1 (1R,2S,3R)-2-pentyl-1-tetrahydropyranyloxy-3-tosyloxymethylcyclopentane 
• 155016-10-7 (3S,4S)-3-pentyl-6-tosyloxyhexan-4-olide 
• 155016-07-2 (3S,4S)-3-pentyl-5-tosyloxypentan-4-olide 
• 155016-13-0 (1R,2S,3R)-3-tosyloxymethyl-2-pentyl-1-cyclopentanol 
• 155016-15-2 (1R,2S,3R)-3-cyanomethyl-2-pentyl-1-tetrahydropyranyloxycyclopentane 
• 155016-08-3 isopropyl (3S,4S)-4,5-epoxy-3-pentylpentanoate 
• 155016-06-1 1,6-anhydro-3,4-dideoxy-4-C-pentyl-β-D-erythro-hexopyranos-2-ulose 
• 155016-09-4 (3S,4S)-6-hydroxy-3-pentyl-4-hexanolide 
• 155016-11-8 (1R,4S,7S)-7-pentyl-2-oxabicyclo<2.2.1>heptan-3-one 
• 155016-12-9 (1R,2S,3R)-3-hydroxymethyl-2-pentyl-1-cyclopentanol 

Downstream Products

• 2570-03-8 (+/-)-methyl trans-dihydrojasmonate 
• 96844-45-0 (+)-9,10-dihydro-7-iso-jasmonic acid 

Relevant articles and documents

Method for synthesizing (1R,2S)-methyl dihydrojasmonate

The invention discloses a novel method for synthesizing (1R,2S)-methyl dihydrojasmonate by using an asymmetric Michael addition reaction. The method comprises the steps: firstly, subjecting cyclopentanone, which serves as a starting raw material, to an aldol reaction with n-valeraldehyde under alkaline conditions to produce 2-pentylidene cyclopentanone 2, and then, carrying out double-bond transposition under acidic conditions, so as to obtain 2-n-pentyl-2-cyclopentenone 3; then, carrying out a Michael addition reaction with dimethyl malonate in the presence of a chiral amino-acid lithium salt, and carrying out silicagel-column chromatographic separation twice, so as to obtain (1S,2S)-2-n-pentyl-3-dimethyl malonate cyclopentanone 4; and finally, carrying out a hydrolyzed decarboxylation reaction, thereby obtaining (1R,2S)-methyl dihydrojasmonate. According to the method, the synthesis route is simple and direct, the reaction conditions are mild, and the target compound can be prepared by only four-step reactions.

A general enantioselective approach to jasmonoid fragrances: Synthesis of (+)-(1R,2S)-methyl dihydrojasmonate and (+)-(1R,2S)-magnolione

Methyl dihydrojasmonate 1 and magnolione 3 are of both academic and industrial interest. In this paper, we describe a flexible, high-yielding route to diastereomerically pure (+)-cis-(1R,2S)-methyl dihydrojasmonate 1 and the first synthesis of (+)-cis-(1R

Synthesis of (±)-methyl epijasmonate and (±)-methyl dihydroepijasmonate by diastereoselective protonation

The synthesis of (±)-methyl epijasmonate (1) was carried out by Michael addition of lithium diallylcuprate to enone 3 and diastereoselective enolate protonation with the chelating proton source 2-(methyliminomethyl)phenol (4; 85% ds), followed by ozonolysis, oxidation, esterification, and Lindlar hydrogenation. During the ozonisation, epimerization to the thermodynamically more stable trans-isomer takes place to some extent, so that 1 was isolated with a cis:trans ratio of 72:28. The analogous transformation of enone 7 with lithium diallylcuprate and 2-(methyliminomethyl)phenol (4) furnished ketone 8 with 94% ds; this was then transformed into (±)-methyl dihydroepijasmonate (2) with a cis:trans ratio of 91:9. The olfactory properties of this product are superior to those available from commercial sources.