cis-cyclooctane-1,2-dithiol | 1190326-25-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 英文名称: cis-cyclooctane-1,2-dithiol
• 英文别名: (1S,2R)-cyclooctane-1,2-dithiol
• CAS: 1190326-25-0
• 化学式: C₈H₁₆S₂
• 分子量: 176.347
• InChiKey: GHCRQUUKLYGYBU-OCAPTIKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-cyclooctane-1,2-dithiol 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以5%的产率得到2,3,12,13-tetrathia-cis-transoid-cis-tricyclo[12.6.0.0^4,11]icosane
  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：

  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

文献信息

• Synthesis, Structure, and Catalytic Activity of Bimetallic Pt ^II –Ir ^III Complexes Bridged by Cyclooctane‐1,2‐dithiolato Ligands
  作者：Norio Nakata、Masahiro Sakashita、Chizuru Komatsubara、Akihiko Ishii

  DOI：10.1002/ejic.200900958

  日期：2010.1

  heterobimetallic complexes bridged by cyclooctane-1,2-dithiolato ligands [(PPh 3 ) 2 Pt(μ 2 -SRS)IrCl(η 5 -Cp*)][SbF 6 ] [R = cis-C 8 H 14 (5), trans-C 8 H 14 (6), Cp* = C 5 Me 5 ] were synthesized by reaction of (cyclooctane-1,2-dithiolato)-Pt II complexes [Pt(SRS)(PPh 3 ) 2 ] [R = cis-C 8 H 14 (3), trans-C 8 H 14 (4)] with [IrCl(μ-Cl)(η 5 -Cp*)] 2 in thf in the presence of AgSbF 6 . The structures of complexes

  由环辛烷-1,2-二硫醇基配体桥接的阳离子 Pt II -Ir III 异双金属配合物 [(PPh 3 ) 2 Pt(μ 2 -SRS)IrCl(η 5 -Cp*)][SbF 6 ] [R = cis-C 8 H 14 (5), 反式-C 8 H 14 (6), Cp* = C 5 Me 5 ]是通过(环辛烷-1,2-二硫醇基)-Pt II复合物[Pt(SRS)(PPh 3 ) 2 ] [R = cis-C 8 H 14 (3), trans-C 8 H 14 (4)] 与 [IrCl(μ-Cl)(η 5 -Cp*)] 2 在 thf 存在下AgSbF 6 。配合物 5 和 6 的结构由它们的 NMR 光谱数据完全表征。此外，5 的 X 射线晶体学分析显示 PtS 2 Ir 核呈现铰链排列，其中顺式-环辛烷-1,2-二硫醇盐充当铂和铱金属之间的桥接配体。配合物 5 和 6 在末端炔烃 R'CCH