cis/trans-2,3-Di(3-cyclohexenyl)thiirane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环丙烷
• 英文名称: cis/trans-2,3-Di(3-cyclohexenyl)thiirane
• 英文别名: 2,3-di(cyclohex-3-en-1-yl)thiirane
• 化学式: C₁₄H₂₀S
• 分子量: 220.379
• InChiKey: XCUNLYLLDMLRLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  cis/trans-2,3-Di(3-cyclohexenyl)thiirane 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-1,2-Di(3-cyclohexenyl)ethylene 、 (E)-1,2-Di(3-cyclohexenyl)ethylene
  参考文献：
  名称：

  Stereoselective synthesis of unhindered olefins by 2-fold extrusion reactions

  摘要：

  Two-fold extrusion reactions of 1,3,4-thiadiazolines 1 provide a convenient stereoselective route to unhindered Z-olefins. An improved preparation of the thiadiazolines involves reaction of an aldehyde with H2S-hydrazine, followed by in situ oxidation of the intermediate predominantly trans thiadiazolidine 2. Stereospecific extrusion of nitrogen yields the cis-thiirane which upon treatment with triphenylphosphine affords the corresponding Z-alkene in good yields.

  DOI：

  10.1021/jo00053a013
• 作为产物：
  描述：

  3-环己烯甲醛 在 lead(IV) acetate 、 硫化氢 、 calcium carbonate 、 肼 作用下， 以 四氢呋喃 为溶剂， 生成 cis/trans-2,3-Di(3-cyclohexenyl)thiirane
  参考文献：
  名称：

  Stereoselective synthesis of unhindered olefins by 2-fold extrusion reactions

  摘要：

  Two-fold extrusion reactions of 1,3,4-thiadiazolines 1 provide a convenient stereoselective route to unhindered Z-olefins. An improved preparation of the thiadiazolines involves reaction of an aldehyde with H2S-hydrazine, followed by in situ oxidation of the intermediate predominantly trans thiadiazolidine 2. Stereospecific extrusion of nitrogen yields the cis-thiirane which upon treatment with triphenylphosphine affords the corresponding Z-alkene in good yields.

  DOI：

  10.1021/jo00053a013

文献信息

• Stereoselective synthesis of unhindered olefins by 2-fold extrusion reactions
  作者：Luis R. Collazo、Frank S. Guziec

  DOI：10.1021/jo00053a013

  日期：1993.1

  Two-fold extrusion reactions of 1,3,4-thiadiazolines 1 provide a convenient stereoselective route to unhindered Z-olefins. An improved preparation of the thiadiazolines involves reaction of an aldehyde with H2S-hydrazine, followed by in situ oxidation of the intermediate predominantly trans thiadiazolidine 2. Stereospecific extrusion of nitrogen yields the cis-thiirane which upon treatment with triphenylphosphine affords the corresponding Z-alkene in good yields.