Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP),The Journal of Organic Chemistry

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Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-06-24 , DOI: 10.1021/acs.joc.1c00977
Vasyl Ripenko ₁ , Daniil Vysochyn ₁ , Ivan Klymov ₁ , Serhii Zhersh ₁ , Pavel K Mykhailiuk ₁

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In flow photochemical addition of propellane to diacetyl allowed construction of the bicyclo[1.1.1]pentane (BCP) core in a 1 kg scale within 1 day. Haloform reaction of the formed diketone in batch afforded bicyclo[1.1.1]pentane-1,3-dicarboxylic acid in a multigram amount. Representative gram scale transformations of the diacid were also performed to obtain various BCP-containing building blocks—alcohols, acids, amines, trifluoroborates, amino acids, etc.—for medicinal chemistry.

中文翻译：

双环[1.1.1]戊烷-1,3-二羧酸（BCP）的大规模合成和改性

在流动中将推进剂光化学添加到双乙酰允许在 1 天内构建 1 kg 规模的双环 [1.1.1] 戊烷 (BCP) 核心。分批形成的二酮的卤仿反应得到数克量的双环[1.1.1]戊烷-1,3-二羧酸。还进行了二酸的代表性克级转化，以获得用于药物化学的各种含 BCP 的结构单元——醇、酸、胺、三氟硼酸盐、氨基酸等。

更新日期：2021-06-24

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