1-<(4-Methoxybenzyl)thio>hexane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-<(4-Methoxybenzyl)thio>hexane
• 英文别名: 1-(Hexylsulfanylmethyl)-4-methoxybenzene
• 化学式: C₁₄H₂₂OS
• 分子量: 238.394
• InChiKey: ZBUSOZLSYHUDMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-己烯 、 4-甲氧基苄硫醇 在 偶氮二异丁腈 作用下， 以 苯 为溶剂， 反应 2.0h， 以90%的产率得到1-<(4-Methoxybenzyl)thio>hexane
  参考文献：
  名称：

  Free-Radical Addition of Alkanethiols to Alkynes. Rearrangements of the Intermediate .beta.-(Vinylthio) Radicals

  摘要：

  A variety of 2-mercapto-substituted vinyl radicals have been produced through the free-radical reaction of alkanethiols (including phenethyl, allyl, and benzyl mercaptans) with monosubstituted acetylenes in benzene at 90 degrees C. The 8-(benzylthio)vinyl radicals 6 readily rearranged to (vinylthio)methyl radicals 7 via a novel 1,4-migration of the phenyl group from thiomethyl to vinyl carbon; 2- (phenethylthio)vinyl radicals 12 underwent internal 1,5-hydrogen transfer to form beta-thio-substituted benzyl radicals 13 which in turn suffered fast beta-elimination of vinylthio radicals 18; and 2-(allylthio)vinyl radical 20 underwent kinetically preferred 5-exo cyclization to give the primary radical 26 which could easily rearrange to the more stable ring-expanded radical 25.

  DOI：

  10.1021/jo00089a030

文献信息

• Free-Radical Addition of Alkanethiols to Alkynes. Rearrangements of the Intermediate .beta.-(Vinylthio) Radicals
  作者：Luisa Benati、Laura Capella、Pier Carlo Montevecchi、Piero Spagnolo

  DOI：10.1021/jo00089a030

  日期：1994.5

  A variety of 2-mercapto-substituted vinyl radicals have been produced through the free-radical reaction of alkanethiols (including phenethyl, allyl, and benzyl mercaptans) with monosubstituted acetylenes in benzene at 90 degrees C. The 8-(benzylthio)vinyl radicals 6 readily rearranged to (vinylthio)methyl radicals 7 via a novel 1,4-migration of the phenyl group from thiomethyl to vinyl carbon; 2- (phenethylthio)vinyl radicals 12 underwent internal 1,5-hydrogen transfer to form beta-thio-substituted benzyl radicals 13 which in turn suffered fast beta-elimination of vinylthio radicals 18; and 2-(allylthio)vinyl radical 20 underwent kinetically preferred 5-exo cyclization to give the primary radical 26 which could easily rearrange to the more stable ring-expanded radical 25.