掩飾對苯醌的環丙烷化反應之研究

Study on the cyclopropanation of Masked p-benzoquinones

鄭曉玲(Hsiao-Ling Cheng)

指導教授 ： 吳吉輝

中原大學/理學院/化學研究所/碩士(2012年)

https://doi.org/10.6840/cycu201200868

摘要

本研究利用2-取代基-4-甲氧酚，成功合成出各種不同官能基的掩飾對苯醌化合物(MPBs) 49、54、58及63。分別和Corey-Chaykovsky試劑反應，進行環丙烷化反應，得到雙環[4.1.0]庚烯酮50、55、59和64，在此我們發現，拉電子基與推電子基的電子效應對Corey-Chaykovsky試劑與掩飾對苯醌上的雙鍵，進行環丙烷化反應的位置會有不同， 接著經由水解得到雙酮化合物51、56、60和65；我們亦將雙環[4.1.0]庚烯酮化合物50及59與不同的格林納試劑進行反應，得到酮類化合物的前驅物68及69。

關鍵字

環丙烷化反應 ； 掩飾對苯醌

並列摘要

The present studies were 2-substituted-4-meethoxyphenol as starting materials to prepare different kinds of masked p-benzoquinones (MPBs) 49, 54, 58 and 63. These compounds subsequently underwent cyclopropanation with Corey-Chaykovsky reagent to obtain bicycle[4.1.0]heptenones 50, 55, 59 and 64. We have found that the effects of electron-withdrawing group and electron donating group will cause the rigioselectivity of the cyclopropanation of MPB’s double bonds. After hydrolysis, the diketones 51, 56, 60 and 65 were obtained. Wealso treated bicycle [4.1.0] heptenone 50 and 59 with Grignard reagents to generate the precursors 68 and 69 of troponoids.

並列關鍵字

cyclopropanation ； Masked p-benzoquinones

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