丁基

在有机化学中，丁基（英語：Butyl group）是一种含四个碳的烷基自由基或官能团，具有通用化学式-C4H9，从两个丁烷异构体中的任意一个衍生而来。

异构体正丁烷（即直链烷烃）中的两个端基碳原子或中间的两个碳原子可连接其他基团，得到两种“丁基”基团：

  • 正丁基或n-丁基：CH3–CH2–CH2–CH2– （系统命名：丁基）
  • 仲丁基或sec-丁基：CH3–CH2–CH(CH3)– （系统命名：1-甲基丙基）

第二种异构体异丁基，即丁烷的支链烷烃异构体，它的中心三级碳原子或者三个一级碳原子可以分别连接其他基团，得到另两种“丁基”基团：

  • 异丁基: (CH3)2CH–CH2– （系统命名：2-甲基丙基）
  • 叔丁基、tert-丁基（也译“特丁基”）或t-丁基: (CH3)3C– （系统命名：1,1-二甲基乙基）

注：丁基的第二、三异构在台湾一般直接按数字命名，在中国大陆则是以“伯仲叔季”称呼。

命名法

键线式 俗名 IUPAC名 系統標準名
正丁基 丁基 丁基
异丁基 2-甲基丙基 2-甲基丙基
仲丁基 丁-2-基 1-甲基丙基
叔丁基 叔丁基 1,1-二甲基乙基

其中丁基是俗名当中最广泛的称谓，而可以适用于所有的异构体。

举例

以下是“乙酸丁酯”的异构体：

butyl acetate isobutyl acetate sec-butyl acetate tert-butyl acetate
乙酸正丁酯
乙酸异丁酯
乙酸仲丁酯
乙酸叔丁酯

叔丁基效应

叔丁基取代基是一种位阻很大的基团，常与其他大位阻基团一起用于化学合成中的动力学稳定，如相关的三甲基硅基基团。叔丁基对于化学反应进程施加的影响称为：“叔丁基效应”。该效应通过狄尔斯－阿尔德反应演绎如下：叔丁基取代基的反应速率比起氢原子作为取代基提高了240倍。[1]

Tert-butyl effect
Tert-butyl effect

参见

参考文献

  1. ^ Factors affecting ease of ring formation. The effect of anchoring substitution on the rate of an intramolecular diels-alder reaction with furan-diene Serge Cauwberghs and Pierre J. De Clercq B. Tinant and J. P. Declercq Tetrahedron Letters Volume 29, Issue 20 , 1988, Pages 2493-2496 doi:10.1016/S0040-4039(00)87916-2

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