A Fluorogenic Aldehyde Bearing a 1,2,3-Triazole Moiety for Monitoring the Progress of Aldol Reactions
A Fluorogenic Aldehyde Bearing a 1,2,3-Triazole Moiety for Monitoring the Progress of Aldol Reactions
复制标题
DOI：
10.1021/jo900013w
复制
发表时间：
2009-03-20
影响因子：
3.6
通讯作者：
Tanaka, Fujie
中科院分区：
文献类型：
--
作者：
Guo, Hai-Ming;Tanaka, Fujie
我们开发了一种带有 1,2,3-三唑部分的新型荧光醛，可用于通过荧光增加来监测羟醛反应的进展。 6-甲氧基-2-萘醛具有高荧光性，而荧光醛（通过 1,2,3-三唑部分连接到 6-甲氧基-2-萘基的 4-甲酰基苯）在水溶液中基本上不发荧光。我们建议 4-甲酰基苯基作为猝灭剂来抑制 6-甲氧基-2-萘基三唑部分的荧光。该醛的羟醛反应产物不具有猝灭部分，并且显示出比醛高800倍以上的荧光。通过筛选羟醛催化剂、对催化剂活性进行排序以及评估反应条件来验证使用荧光醛的测定系统。
We have developed a new type of fluorogenic aldehyde bearing a 1,2,3-triazole moiety that is useful for monitoring the progress of aldol reactions through an increase in fluorescence. Whereas 6-methoxy-2-naphthaldehyde was highly fluorescent, the fluorogenic aldehyde, 4-formylbenzene connected to the 6-methoxy-2-naphthyl group through a 1,2,3-triazole moiety, was essentially nonfluorescent in aqueous solutions. We suggest that the 4-formylphenyl group acts as a quencher to suppress the fluorescence of the 6-methoxy-2-naphthyltriazole moiety. The product of the aldol reaction of this aldehyde does not have a quenching moiety and showed more than 800-fold higher fluorescence than the aldehyde. Assay systems using the fluorogenic aldehyde were validated by screening of aldol catalysts, ranking of the activities of the catalysts, and evaluation of reaction conditions.