Cargando…

Facile Synthesis and Preferred Conformation Analysis of Cyclododeceno[b]indene

Using methanesulfonic acid as a catalyst, a series of cyclododeceno[b]indene derivatives were synthesized by the cyclization of α-benzylcyclododecanones, which were prepared by the reactions of cyclododecanones with a variety of substituted benzyl chlorides or bromides using NaH as a base. Their str...

Descripción completa

Detalles Bibliográficos
Autores principales: Zhang, Chunyan, Gong, Shengyan, Zhang, Li, Wang, Daoquan, Wang, Mingan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6263188/
https://www.ncbi.nlm.nih.gov/pubmed/20335940
http://dx.doi.org/10.3390/molecules15020699
Descripción
Sumario:Using methanesulfonic acid as a catalyst, a series of cyclododeceno[b]indene derivatives were synthesized by the cyclization of α-benzylcyclododecanones, which were prepared by the reactions of cyclododecanones with a variety of substituted benzyl chlorides or bromides using NaH as a base. Their structures were confirmed by mp, IR spectra, (1)H-NMR, (13)C-NMR, MS, and x-ray diffraction. The preferred conformations were analyzed by crystal structure, (1)H-NMR and quantum chemistry calculations, and compared with the x-ray diffraction structure of 2,3,5,6-bis(ortho-1,10-decylidene)dihydropyrazine. The results showed that the cyclododecene moiety adopted a preferred [1ene2333] conformation, and the substituted groups at aromatic ring had no significant influence on the conformation.