2-thiomethyl-2-butenenitrile

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-thiomethyl-2-butenenitrile
• 英文别名: (Z)-2-methylsulfanylbut-2-enenitrile
• 化学式: C₅H₇NS
• 分子量: 113.183
• InChiKey: CQNPVNJFUDXALW-HYXAFXHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  硫氰酸甲酯 、 反式-巴豆腈(含有约20的顺式同分异构体) 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以28%的产率得到2-thiomethyl-2-butenenitrile
  参考文献：
  名称：

  Simple and Efficient Preparation of [10,20-¹³C₂]- and [10-CH₃,13-¹³C₂]-10-Methylretinal:  Introduction of Substituents at the 2-Position of 2,3-Unsaturated Nitriles

  摘要：

  In this paper, we present the synthesis of [10,20-C-13(2)] -10-methylretinal and [10-CH3,13-C-13(2)] -10-methylretinal, two doubly C-13-labeled chemically modified retinals that have been recently used to study the structural and functional details behind the photocascade of bovine rhodopsin (Verdegem et al. Biochemistry 1999, 38, 11316; de Lange et al. Biochemistry 1998, 37, 1411). To obtain both doubly C-13-labeled compounds, we developed a novel synthetic method to directly and regiospecifically introduce a methyl substituent on the 2-position of 3-methyl-5-(2',6',6'-trimethyl-1'cyclohexen-1'-yl)-2,4-pentadienenitrile. Encouraged by these results, we investigated the scope of this novel reaction by developing a general method for the introduction of a variety of substituents to the 2-position of 3-methyl-2,3-unsaturated nitriles, paving the way for simple and efficient synthesis of a wide variety of 10-, 14-, and 10,14-substituted chemically modified retinals, and other biologically important compounds.

  DOI：

  10.1021/jo0009595

文献信息

• Simple and Efficient Preparation of [10,20-¹³C₂]- and [10-CH₃,13-¹³C₂]-10-Methylretinal:  Introduction of Substituents at the 2-Position of 2,3-Unsaturated Nitriles
  作者：Peter J. E. Verdegem、Menno C. F. Monnee、Johan Lugtenburg

  DOI：10.1021/jo0009595

  日期：2001.2.1

  In this paper, we present the synthesis of [10,20-C-13(2)] -10-methylretinal and [10-CH3,13-C-13(2)] -10-methylretinal, two doubly C-13-labeled chemically modified retinals that have been recently used to study the structural and functional details behind the photocascade of bovine rhodopsin (Verdegem et al. Biochemistry 1999, 38, 11316; de Lange et al. Biochemistry 1998, 37, 1411). To obtain both doubly C-13-labeled compounds, we developed a novel synthetic method to directly and regiospecifically introduce a methyl substituent on the 2-position of 3-methyl-5-(2',6',6'-trimethyl-1'cyclohexen-1'-yl)-2,4-pentadienenitrile. Encouraged by these results, we investigated the scope of this novel reaction by developing a general method for the introduction of a variety of substituents to the 2-position of 3-methyl-2,3-unsaturated nitriles, paving the way for simple and efficient synthesis of a wide variety of 10-, 14-, and 10,14-substituted chemically modified retinals, and other biologically important compounds.