南方科技大学Wei Jiang研究组在有机化学研究中取得进展。他们利用endo-官能化的容器分子实现了水中的亚胺和半胺类化合物的稳定化。相关论文发表在2022年7月6日出版的《德国应用化学》杂志上。

在该研究中，团队发现不稳定的亚胺和半胺官能团可以在一种合成的容器分子——一种水溶性萘管——中实现稳定化。这种萘管在具有氢键位点和疏水表面的空腔中锚定有伯胺基。在本体水溶液中的醛被胺困在腔内，形成被氢键和疏水作用稳定的半胺。疏水微环境中水的释放有利于半胺脱水生成亚胺。核磁共振波谱和质谱可以在室温下检测到半胺和亚胺的存在。

据了解，稳定对水敏感的反应中间体是具有挑战性的，但对于引导水相反应生成所需的产物来说是需要的。

附：英文原文

Title: Stabilization of Imines and Hemiaminals in Water by an Endo-Functionalized Container Molecule

Author: Ming-Shuang Li, Yi-Wei Dong, Mao Quan, Wei Jiang

Issue&Volume: 2022-07-06

Abstract: Stabilizing water-sensitive reaction intermediates is challenging but desirable for guiding reactions to desired products in water. Herein, we report that labile imine and hemiaminal functional groups can be stabilized inside a synthetic container compound, a water-soluble naphthotube. The naphthotube features a primary amine group anchored in a cavity with both hydrogen bonding sites and hydrophobic surfaces. Aldehydes in bulk aqueous solution are trapped in the cavity by the amine to form hemiaminals stabilized through hydrogen bonding and hydrophobic effects. Dehydration of the hemiaminal to the imine is favored by the release of water from the hydrophobic microenvironment. Both hemiaminal and imine can be detected at room temperature by NMR spectroscopy and mass spectrometry.

DOI: 10.1002/anie.202208508

Source: https://onlinelibrary.wiley.com/doi/10.1002/anie.202208508