NOVEL CHEMISTRY OF CYCLOPROPANONE HYDRATES

一系列新的官能化环丙酮水合物将是 合成的。早期的合成困难已经通过制作 在起始酮缩醛中使用环缩酮。这让我们收获了丰硕的成果 与重氮乙腈和重氮乙酸乙酯反应生成 相应的环丙酮、缩腈和酯。通过以下方式减少 氢化铝锂分别生成胺和醇。这些 物质及其类似物将用于建造一种新的 以环丙酮水合物为活性的系列酶抑制剂 捕捉剂。一些酶的潜在抑制剂，包括 胰凝乳酶、木瓜酶、转化酶、弹性蛋白酶和HMG-CoA还原酶 建议。 从同一组前体中，一种不同寻常的全碳1，3偶极将是 探索过了。有人建议，这种物质可以用于新的、直接的 环戊酮和环戊酮环化反应。此外，一个新的 贝塔-烯醇酸等效物将从这一系列保护中开发出来 环丙酮。最后，背后的潜在机制原因 环缩酮与非环缩酮的反常稳定性 将探索环丙酮类化合物。

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.