cis-9,10,11-trithiabicyclo[6.3.0]undecane | 1190326-10-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: cis-9,10,11-trithiabicyclo[6.3.0]undecane
• 英文别名: (3aS,9aR)-3a,4,5,6,7,8,9,9a-octahydrocycloocta[d]trithiole
• CAS: 1190326-10-3
• 化学式: C₈H₁₄S₃
• 分子量: 206.397
• InChiKey: BCNQYPLDBPXQFI-OCAPTIKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-9,10,11-trithiabicyclo[6.3.0]undecane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以76%的产率得到cis-cyclooctane-1,2-dithiol
  参考文献：
  名称：

  Oxidation and Reduction Reactions of cis-9,10,11-Trithiabicyclo[6.3.0]undecane Synthesized by Reaction of cis-Cyclooctene with S₈O

  摘要：

  cis-Cyclooctene reacted with S8O in refluxing carbon disulfide to give cis-9,10,11-trithiabicyclo[6.3.0]undecane (1,2,3-trithiolane). Oxidation of the 1,2,3-trithiolane with m-chloroperbenzoic acid (MCPBA) or dimethyldioxirane (DMD) yielded the corresponding 1-exo-oxide, 1-endo-oxide, 2-endo-oxide, 2-exo-oxide, 1-endo,3-exo-dioxide, 1-exo,3-exo-dioxide, 1,1,3-exo-trioxide, and 1,1,3,3-tetraoxide, depending on the amount of the oxidants. Formation of another 1,3-dioxide assignable to the 1-endo,3-endo-dioxide was observed in the oxidation of the 1-endo-oxide with MCPBA. Oxidation of the 2-exo-oxide with DMD gave the 1,1,3,3-tetraoxide in low yield. Reduction of the 1,2,3-trithiolane and its trans isomer with LiAlH4 gave cis- and trans-cyclooctane-1,2-dithiol, respectively, in high yields. Oxidation of the sodium salt of the cis-1,2-dithiol with MCPBA provided the corresponding 1,2,5,6-tetrathiocane in low yield as the only identifiable product.

  DOI：

  10.1080/10426500902855232
• 作为产物：
  描述：

  顺-环辛烯 在 cyclooctasulfur monoxide 作用下， 以 二硫化碳 为溶剂， 反应 1.0h， 以10%的产率得到cis-9,10,11-trithiabicyclo[6.3.0]undecane
  参考文献：
  名称：

  Oxidation and Reduction Reactions of cis-9,10,11-Trithiabicyclo[6.3.0]undecane Synthesized by Reaction of cis-Cyclooctene with S₈O

  摘要：

  cis-Cyclooctene reacted with S8O in refluxing carbon disulfide to give cis-9,10,11-trithiabicyclo[6.3.0]undecane (1,2,3-trithiolane). Oxidation of the 1,2,3-trithiolane with m-chloroperbenzoic acid (MCPBA) or dimethyldioxirane (DMD) yielded the corresponding 1-exo-oxide, 1-endo-oxide, 2-endo-oxide, 2-exo-oxide, 1-endo,3-exo-dioxide, 1-exo,3-exo-dioxide, 1,1,3-exo-trioxide, and 1,1,3,3-tetraoxide, depending on the amount of the oxidants. Formation of another 1,3-dioxide assignable to the 1-endo,3-endo-dioxide was observed in the oxidation of the 1-endo-oxide with MCPBA. Oxidation of the 2-exo-oxide with DMD gave the 1,1,3,3-tetraoxide in low yield. Reduction of the 1,2,3-trithiolane and its trans isomer with LiAlH4 gave cis- and trans-cyclooctane-1,2-dithiol, respectively, in high yields. Oxidation of the sodium salt of the cis-1,2-dithiol with MCPBA provided the corresponding 1,2,5,6-tetrathiocane in low yield as the only identifiable product.

  DOI：

  10.1080/10426500902855232