Allyl 2-iodobenzyl sulfide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Allyl 2-iodobenzyl sulfide
• 英文别名: 1-Iodo-2-(prop-2-enylsulfanylmethyl)benzene
• 化学式: C₁₀H₁₁IS
• 分子量: 290.168
• InChiKey: HFKHNQRWMSIRFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  烯丙硫醇 、 邻碘氯苄 在 sodium hydroxide 、 三异辛胺 作用下， 以 水 、 甲苯 为溶剂， 反应 1.0h， 以90%的产率得到Allyl 2-iodobenzyl sulfide
  参考文献：
  名称：

  Palladium-Mediated Intramolecular Formation of a C-S Bond: Application to the Selective Syntheses of Six- and Seven-Membered Sulfur-Containing Heterocycles

  摘要：

  Cyclopalladated complexes derived from benzylmethyl sulfide, o-iodo sulfides, or methyl-2-biphenyl sulfide react with alkynes to give stable organometallic compounds whereby the alkyne has inserted in the carbon-palladium bond. Activation of these complexes was effected by treatment with a silver salt, and resulting thermolysis led to a selective depalladation process, affording a series of both neutral and cationic 1H-2S-benzothiopyran derivatives. With dissymmetric alkynes this reaction displayed a high degree of regiocontrol. Under similar conditions, a new entry for the synthesis of derivatives of the rare family of dibenzo[bd]thiepins was acheived.

  DOI：

  10.1021/jo00109a036

文献信息

• Palladium-Mediated Intramolecular Formation of a C-S Bond: Application to the Selective Syntheses of Six- and Seven-Membered Sulfur-Containing Heterocycles
  作者：John Spencer、Michel Pfeffer、Andre DeCian、Jean Fischer

  DOI：10.1021/jo00109a036

  日期：1995.2

  Cyclopalladated complexes derived from benzylmethyl sulfide, o-iodo sulfides, or methyl-2-biphenyl sulfide react with alkynes to give stable organometallic compounds whereby the alkyne has inserted in the carbon-palladium bond. Activation of these complexes was effected by treatment with a silver salt, and resulting thermolysis led to a selective depalladation process, affording a series of both neutral and cationic 1H-2S-benzothiopyran derivatives. With dissymmetric alkynes this reaction displayed a high degree of regiocontrol. Under similar conditions, a new entry for the synthesis of derivatives of the rare family of dibenzo[bd]thiepins was acheived.