NOVEL CHEMISTRY OF CYCLOPROPANONE HYDRATES

一系列新的官能化环丙酮水合物将是 合成了 早期的合成困难已经被克服， 在起始烯酮缩醛中使用环状缩酮。 这使得富有成效的 与重氮乙腈和重氮乙酸乙酯反应，得到 相应的环丙酮缩酮腈和酯。 还原 氢化铝锂分别得到胺和醇。 这些 物质及其类似物将用于构建新的 以环丙酮水合物为活性成分的系列酶抑制剂 捕集剂 许多酶的潜在抑制剂，包括 胰凝乳蛋白酶、木瓜蛋白酶、转化酶、弹性蛋白酶和HMG-CoA还原酶， 建议道。 从同一组前体中，将得到一种不寻常的全碳1，3-偶极子。 探讨了 建议这些物质可用于新的、直接的 环戊酮和环戊烯酮成环反应。 一种新 β-烯醇化物等价物将从这一系列受保护的 环丙烷酮。 最后，我们分析了这一现象背后的内在机制原因， 不寻常的稳定性的环状与非环状缩酮的 将探索环丙酮。

A novel series of functionalized cylopropanone hydrates will be synthesized. Earlier synthetic difficulties have been overcome by making use of a cyclic ketal in the starting ketene acetal. This permits fruitful reaction with diazoacetonitrile and ethyl diazoacetate yielding the corresponding cyclopropanone ketal nitrile and ester. Reduction with lithium aluminum hydride yielded the amine and alcohol respectively. These substances and their analogues will be used in the construction of a new series of enzyme inhibitor with the cyclopropanone hydrate as the active trapping agent. Potential inhibitors for a number of enzymes, including chymotrypsin, papain,converting enzyme, elastase and HMG-CoA reductase, are suggested. From the same set of precursors, an unusual all-carbon 1,3-dipole will be explored. It is proposed that such substances might be used in new, direct cyclopentanone and cyclopentenone annulation reactions. In addition, a new Beta-enolate equivalent will be developed from this series of protected cyclopropanones. Finally, the underlying mechanistic reasons behind the unusual stability of the cyclic versus the non-cyclic ketals of the cyclopropanones will be explored.