林文偉Lin, Wenwei柯有軒Ke, You-Syuan2020-10-19不公開2020-10-192019http://etds.lib.ntnu.edu.tw/cgi-bin/gs32/gsweb.cgi?o=dstdcdr&s=id=%22G060642016S%22.&%22.id.&http://rportal.lib.ntnu.edu.tw:80/handle/20.500.12235/111095近年來，本實驗室開發出一系列具有α,β-不飽和羰基的化合物作為起始物，並在有機膦試劑作用下，能得到β位醯化反應 (β-acylation)的產物，接著我們嘗試改變我們起始物的結構，使用鏈狀的α,β-不飽和羰基的化合物期望一樣能進行β位醯化反應。 首先我們利用查爾酮衍生物，其同樣具有α,β-不飽和羰基的結構，能在膦試劑的作用下進行β位醯化反應，並利用控制實驗探討其進行β位醯化反應的成因以及限制。 同時我們也嘗試改變起始物結構，以肉桂酸在鹼試劑的條件下與醯氯反應得到具有α,β-不飽和羰基結構的酸酐，接著會經由β位醯化反應的中間產物，其會繼續被膦試劑加成，最終得到呋喃酮的產物。We report an organophosphane-promoted direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides in presence of the base. The systematic mechanistic investigations reveal that the α,β-unsaturated 1,3-diketone with electron-donating group at 2nd position favours the reaction toward the formation of β-acylated products where electron-withdrawing group follows the reaction toward the C-acylation/cyclization sequence. The obtained β-acylation adducts could be further transformed into furan derivatives. The method for the synthesis of 2-furanones was also demonstrated by the reaction of cinnamic acid derivatives and acyl chlorides via the β-acylation of corresponding cinnamic anhydride derivatives as the key step.有機磷試劑β位醯化反應呋喃酮organophosphaneβ-acylationfuranone