酚酮類化合物之合成

Synthesis of Troponoids from 2-Methoxyphenols via Masked o-Benzoquinones

黃冠勳(Kuan-Hsun Huang)

指導教授 ： 廖俊臣

國立清華大學/理學院/化學系/碩士(2009年)

摘要

本研究成功的利用 Corey-Chaykovsky 試劑與掩飾鄰苯醌反應合
成雙環[4.1.0]庚烯酮化合物，並將其水解、擴環得到酚酮類化合物。
若使用兩當量 Corey-Chaykovsky 試劑與掩飾鄰苯醌反應，得此
類產物可在矽膠作用下重排成為環庚三烯化合物，且此產物預期可作
為酮類化合物之前驅物。

關鍵字

酚酮 ； 與掩飾鄰苯醌 ； 酮類化合物

並列摘要

Abstract
The derivatives of tropolone and tropone with various substituted
groups are seven-membered-ring nonbenzenoid aromatic compounds
some natural products contain such moieties. Furthermore, troponoids
have fascinating biological activities such as antiviral, antitumor, and
antioxidant.
According to our research, the cyclopropanation reactions of MOBs
to give bicyclo[4.1.0]heptenone skeletons were successful with 1 eq. of
Corey-Chaykovsky reagent (CCR). The acid hydrolysis of
dimethoxyketal follow by ring enlargement with lewis acid provided
desired tropolones.
Moreover, epoxide derivatives of bicycle[4.1.0]heptenones which
were obtained when 2 eq. of CCR reacted with MOBs gave
cycloheptatriene derivatives, a potential precursor to tropone upon
treatment with silica gel.

並列關鍵字

Corey-Chaykovsky

參考文獻

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