化学工作者的日常

交流化学知识提高有机水平了解一只有机喵的日常生活与工作

投稿

订阅

订阅数

获赞数

154

阅读数

59.3万

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Mitsunobu反应（光延反应）进行仲醇的手性翻转

松田诚一

NKU

在下松田诚一2020/05/15 00:42:52化学工作者的日常

中文摘要

Mitsunobu反应（光延反应）进行仲醇的手性翻转我的某中间体由不对称烯丙化产生然而所产生的羟基手性不正确，故用Mitsunobu反应（光延反应）进行羟基翻转醇的手性翻转

关键词

有机合成Mitsunobu反应（光延反应）进行仲醇的手性翻转无水无氧操作

Mitsunobu反应（光延反应）机理如下

我的某中间体由不对称烯丙化产生然而所产生的羟基手性不正确，故用Mitsunobu反应（光延反应）进行羟基翻转

$3RT{7_1J{1B(7~DFQES)5L9.png$ （绘图软件：chemdraw）

注：所用条件与图示略有不同，不过原理以及方法相同

先上试剂全家福（THF为活化分子筛提前2天密封干燥处理后的溶剂）

称取1.0227g对硝基苯甲酸

将对硝基苯甲酸加入三颈瓶中，一口插温度计另一口插三通阀，不要忘记加入磁力搅拌子

氩气置换装置内气体，置换3次使之内部氩气氛保护，不要快速充入氩气避免吹散粉末

注射器吸取无水四氢呋喃10ml注入，注入时冲洗瓶壁，洗下被吹起的粉末

注：原图找不到了用取用丁基锂的图片代替，取用无水溶剂的方法和它基本一样

将装置至于冰浴中降温加少量盐当温度计示数将至-2--5℃时开始加入三正丁基膦

正丁基膦易氧化取用时氩气保护

这一步可以快速加入不会有明显温度变化，注意加入时直接滴入反应液不要把三正丁基膦滴在瓶壁上

注射器吸取DIAD缓慢滴加进反应体系，此步会强烈放热

一定要缓慢滴加，保证体系温度维持在0℃以下

加毕，保持在0℃搅30min

底物溶解在少量四氢呋喃中缓慢滴加进反应体系

注：先将底物吸入注射器然后用少量THF洗涤瓶壁，并将洗涤液吸入注射器

此步略有放热小心缓慢滴加

加毕后，继续冰浴搅拌(此时冰已差不多融化完全），TLC监测反映

底物弱紫外，成酯后紫外大大增强

高锰酸钾或者磷钼酸显色

大约1h后反应完成，不淬灭直接旋蒸（加入氯化铵溶液淬灭亦可以），蒸干后加入少量乙醚或者二氯甲烷冲洗并进行柱层析纯化。

在底物的甲醇溶液中滴加甲醇钠甲醇溶液，进行水解

也有说不经纯化直接水解亦可，但是产物比较好分离就纯化一下避免体系太过杂乱

[修改于 5 年前 - 2020/05/15 09:14:47]

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Siberia_09_CIF3 十步芳草

十步芳草

4年7个月前 IP:辽宁

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啊，是松田

我09

梧桐雨西岭雪2

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大佬就是大佬，牛

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话说出了个催化版的光延反应

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