經由掩飾鄰苯醌類合成4-乙氧羰基酚酮類的研究

Synthesis of 4-Ethoxycarbonyltropolones from Masked o-Benzoquinones

張逸專(Chuan-Yi Chang)

中原大學/理學院/化學研究所/碩士(2011年)

https://doi.org/10.6840/cycu201100935

摘要

利用Ethyl (dimethylsulfuranylidene)acetate (EDSA)試劑與掩飾鄰苯醌反應成功的合成雙環[4.1.0]庚烯酮化合物，並將其水解、擴環製得帶有乙氧羰基酚酮類的化合物。且發現擴環後產物結構為64-66的結構，而非過去一般所認知的二氟化硼只接在單邊酮上64’-66’的結構，提供去除二氟化硼非只用酸性溶液的方法也可以使用鹼性溶液的有效去除方法。

關鍵字

掩飾鄰苯醌 ； 酚酮

並列摘要

In this study, ethyl (dimethylsulfuranylidene) acetate (EDSA) was used for
cyclopropanation reaction of MOBs to obtain bicyclo[4.1.0]heptenone systems, which were then converted to 4-ethoxycarbonyltropolones via acid-catalyted hydrolysis of the ketal group, ring expansion by boron trifluoride-ether and hydrolysis the difluoro borates.
Furthermore, the structure of ring enlargement were revised. Difluoroborane is coordinating to both of the oxygen of the diketone forming a five-member ring. The removal of difluoroborane can be done by basic solution.

並列關鍵字

Masked o-Benzoquinones ； tropolones

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