Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
Molecules. 2010 Feb 1;15(2):699-708. doi: 10.3390/molecules15020699.
Using methanesulfonic acid as a catalyst, a series of cyclododeceno[b]indene derivatives were synthesized by the cyclization of alpha-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, 1H-NMR, 13C-NMR, MS, and x-ray diffraction. The preferred conformations were analyzed by crystal structure, 1H-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.
使用甲磺酸作为催化剂，通过α-苄基环十二酮的环化反应，合成了一系列环十二烯并[b]茚衍生物，α-苄基环十二酮是由环十二酮与各种取代的苄基氯或溴在氢化钠作为碱的条件下反应制备的。它们的结构通过熔点、红外光谱、1H-NMR、13C-NMR、MS 和 X 射线衍射得到确认。通过晶体结构、1H-NMR 和量子化学计算对其优势构象进行了分析，并与 2,3,5,6-双（邻-1,10-癸烯）二氢吡嗪的 X 射线衍射结构进行了比较。结果表明，环十二烯部分采用了优先的[1ene2333]构象，芳环上的取代基对构象没有显著影响。
