94323-92-9

Usage

Uses

Used in Organic Synthesis:
(5E)-3a-chloro-5-(chloromethylidene)-4,4-dimethoxy-6a-methyltetrahydrocyclopenta[c]pyrrole-1,3(2H,3aH)-dione is used as a synthetic intermediate for the development of novel organic compounds. Its unique structure and functional groups allow for various chemical reactions, enabling the creation of new molecules with potential applications in different fields.
Used in Medicinal Chemistry:
(5E)-3a-chloro-5-(chloromethylidene)-4,4-dimethoxy-6a-methyltetrahydrocyclopenta[c]pyrrole-1,3(2H,3aH)-dione is used as a lead compound in the discovery and development of new pharmaceutical agents. Its complex structure and functional groups may possess biological activities that can be harnessed for therapeutic purposes. Further research is required to explore its potential as a medicinal compound and to optimize its properties for specific applications.

Upstream product

• 53969-64-5 7,7-dimethoxy-2-exo-methyl-1,4,5,6-tetrachlorobicyclo<2.2.1>hept-5-ene-2-endo-carbonitrile 
• 94294-31-2 1,4,5,6-tetrachloro-7,7-dimethoxy-exo-2-methylbicyclo<2.2.1>hept-5-ene-endo-2-carboxamide 
• 2207-27-4 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene 
• 94294-32-3 3a,5-endo-6-trichloro-6a-ethoxy-4,4-dimethoxy-3-methyl-3,5-methanohexahydrocyclopentapyrrol-2(1H)-one 

Relevant academic research and scientific papers

Synthesis of 2,2-Disubstituted 7-Methylenenorbornanes with 2-Exo Functionality by Diels-Alder Reaction of 5,5-Dimethoxytetrachlorcyclopentadiene

Diels-Alder reaction of 5,5-dimethoxytetrachlorcyclopentadiene (2) with methyl methacrylate gave only the endo-carbomethoxybicycloheptene adduct 4N, confirmed by single-crystal X-ray analysis.Methylation of the endo adduct 3 of methyl acrylate and 2 gave only 4N.Saponification and dehalogenation of 3 gave carboxy ketal 7, whose methyl ester 9 also gave only endo-carbomethoxyproduct 10 upon alkylation.Reaction of 2 with methacrylonitrile gave a 3.5:1 exo/endo product mixture, whose major isomer 11X was hydrolyzed to its carboxamide (12 X).Conversion of 12X to its carboxylic acid (6X) by acidic n-butyl nitrite was accompanied by a pentachloro byproduct (19) derived from internal methoxylation of the carboxy group by the C7 ketal.Dehalogenation of 6X and hydrogenation gave saturated carboxy ketal 20.Hydrolysis of 20 gave the lactol 22 of the keto acid.Treatment of 22 with diazomethane gave keto ester 25; treatment of 20 with diazomethane gave ester 24, whose ketal function could not be selectively hydrolyzed to give 25, only 22 being isolated.Wittig reaction of 25 provided the 7-methylene ester 26, also available by direct Wittig treatment of 22 followed by esterification.