(E)-1-(4-n-Butyl-3-thienyl)-5-cyano-5-methylpent-1-en-3-thiol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-1-(4-n-Butyl-3-thienyl)-5-cyano-5-methylpent-1-en-3-thiol
• 英文别名: (E)-5-(4-butylthiophen-3-yl)-2,2-dimethyl-3-sulfanylpent-4-enenitrile
• 化学式: C₁₅H₂₁NS₂
• 分子量: 279.47
• InChiKey: NBZDGOXGMOLSJB-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-噻吩甲基硫醇 在 偶氮二异丁腈 、 1-己炔 作用下， 以 苯 为溶剂， 反应 2.0h， 以3%的产率得到(E)-1-(4-n-Butyl-3-thienyl)-5-cyano-5-methylpent-1-en-3-thiol
  参考文献：
  名称：

  Free-Radical Addition of Heteroarenethiols and Heteroarylmethanethiols to Hexyne and Phenylacetylene. Chemical Behavior of the Transient .beta.-Sulfanylvinyl Radicals

  摘要：

  The free-radical reaction of a number of heteroarenethiols (including 2-thiophene-, 2-benzo[b]furan-and 2-benzo[b]thiophenethiol) and heteroarylmethanethiols (including 2-furyl-, 2-thienyl-, and 3-thienylmethanethiol) with hex-1-yne and phenylacetylene has been investigated in benzene solution both at 100 degrees C in the presence of AIBN and at room temperature in the presence of BEt(3)/O-2. Under both of these conditions the above thiols generally furnished transient 2-sulfanylvinyl radicals through regioselective addition of corresponding sulfanyl radicals to the terminal alkyne carbon, but 2-benzo[b]furanthiol failed to react with either alkyne in the presence of BEt(3)/O-2 and unexpectedely gave 2-(ethylsulfanyl)benzo[b]furan to a significant extent. The produced 2-(2-heteroarylsulfanyl) vinyl radicals largely preferred to undergo intermolecular H-abstraction reaction rather than intramolecular 5-endo cyclization onto the heteroaryl moiety of the 2-sulfanyl substituent. The 2-[(2-thienylmethyl)sulfanyl]- and, especially, 2-[(2-furylmethyl)sulfanyl]vinyl radicals, besides H-abstraction, promptly underwent intramolecular B-exo cyclization to give spiro radicals that interestingly underwent beta-scission of their respective C-S and C-O bond resulting in ring cleavage of the original heteroaryl group. The 2-[(3-thienylmethyl)sulfanyl]vinyl radicals did not exhibit any similar B-exo cyclization, but did undergo a 6-endo cyclization to a very slight extent.

  DOI：

  10.1021/jo00129a039