1,6-dimercapto-3-thiahexane | 79108-81-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 英文名称: 1,6-dimercapto-3-thiahexane
• 英文别名: 1,4,8-trithiaoctane；3-(2-Sulfanylethylsulfanyl)propane-1-thiol
• CAS: 79108-81-9
• 化学式: C₅H₁₂S₃
• 分子量: 168.348
• InChiKey: RSQCPZJFYJBZDV-UHFFFAOYSA-N

物化性质

• 沸点：
  88-95 °C(Press: 0.1 Torr)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,6-dimercapto-3-thiahexane 在 碘 、 三乙胺 作用下， 以 氯仿 为溶剂， 生成 1,2,5-trithiacyclooctane
  参考文献：
  名称：

  Synthesis of Medium Ring Disulfides by Titrimetry; An Improvement on High Dilution Techniques

  摘要：

  DOI：

  10.1055/s-1981-29481
• 作为产物：
  描述：

  3,7-二硫杂-1,9-壬二硫醇 在 bis(triphenylphosphine)nickel(II) chloride 、 甲基碘化镁 作用下， 以 苯 为溶剂， 反应 18.0h， 以71%的产率得到1,6-dimercapto-3-thiahexane
  参考文献：
  名称：

  Chelation Assistance in the Activation of Csp3-S Bonds in Nickel-Catalyzed Cross-Coupling Reactions

  摘要：

  An unprecedented chelation approach to activate C(sp)3-S bonds in nickel-catalyzed cross-coupling reactions is described. Our theme was based on the formation of a chelation complex which results in the enhancement of the reactivity of aliphatic carbon-sulfur bonds. When two dithioacetal functionalities are located in close proximity, selective olefination of one of these two dithioacetal groups can thus be achieved conveniently. Depending on the relative positions of the newly formed double bond and the remaining dithioacetal group, tandem olefination occurs to give the corresponding 1,5-bis-silyl-substituted pentadienes. Various neighboring heteroatom substituents (OR, OH, NR(2) as well as SR groups) can facilitate the olefination of a dithioacetal group. Poly(thioether) linkage afforded the corresponding degradation products via a B-sulfur elimination process. 1,3-Dimercapto- and 1,3-dithiolatopropanes furnish the cyclopropane formation under nickel-catalyzed reaction conditions. The reaction of a dihydrothiopyran with MeMgI in the presence of the nickel catalyst proceeds via a sulfur-coordinated ir-allyl complex, which can further activate the CS bond to give vinylcyclopropane.

  DOI：

  10.1021/ja00099a009

文献信息

• Synthesis of Enantiomerically Pure Thiocrown Ethers Derived from 1,1‘-Binaphthalene-2,2‘-diol
  作者：H. Thijs Stock、Richard M. Kellogg

  DOI：10.1021/jo952107o

  日期：1996.1.1

  Synthetic methodology is given for the preparation of two different types of thiocrown ethers from optically pure 1,1'-binaphthalene-2,2'-diol (10). The conceptually simplest approach starts from optically pure 10 itself, which is alkylated (4 equiv of K(2)CO(3) in DMF at 110 degrees C) with 2-chloroethanol followed by mesylation to provide 2,2'-bis(2-(mesyloxy)ethoxy)-1,1'-binaphthyl (14). When allowed

  给出了从光学纯的1,1'-联萘-2,2'-二醇（10）制备两种不同类型的硫代冠醚的合成方法。从概念上讲，最简单的方法是从光学纯的10本身开始，将其与2-氯乙醇进行烷基化（在DMF中于110摄氏度时在DMF中为4当量的K（2）CO（3）），然后进行甲磺酰化，以提供2,2'-bis（2 -（甲甲氧基）乙氧基）-1,1'-联萘基（14）。当使其与乙烷-1,2-二硫醇，丙烷-1,3-二硫醇，1,4,7-三噻庚烷，1,4,8,11-四硫十一烷，2,2-二甲基丙烷-1,3-二硫醇反应时，2-（巯基甲基）-1-丙烯-3-硫醇和1,2-苯二硫醇在Cs（2）CO（3）在60°C的DMF中存在时，相应的硫冠醚22-25、28、30 ，以30-54％的产率形成32。进行测试反应以证实在这些条件下在烷基化过程中不发生外消旋化。在相似的条件下，将光学纯的10与四氢吡喃基（THP）保护的3-氯丙醇的反应进行得较慢，但反应较干净。除去THP保护基，得到2
• SETZER, WILLIAM N.;AFSHAR, SHAHRARA;BURNS, NORMAN L.;FERRANTE, LUCILLE A.+, HETEROATOM CHEM., 1,(1990) N5, C. 375-387
  作者：SETZER, WILLIAM N.、AFSHAR, SHAHRARA、BURNS, NORMAN L.、FERRANTE, LUCILLE A.+

  DOI：——

  日期：——
• GOODROW M. H.; MUSKER W. K., SYNTHESIS (BRD), 1981, NO 6, 457-459
  作者：GOODROW M. H.、 MUSKER W. K.

  DOI：——

  日期：——
• Chelation Assistance in the Activation of Csp3-S Bonds in Nickel-Catalyzed Cross-Coupling Reactions
  作者：Ken-Tsung Wong、Tien-Min Yuan、Maw Cherng Wang、Hsiao-Hsian Tung、Tien-Yau Luh

  DOI：10.1021/ja00099a009

  日期：1994.10

  An unprecedented chelation approach to activate C(sp)3-S bonds in nickel-catalyzed cross-coupling reactions is described. Our theme was based on the formation of a chelation complex which results in the enhancement of the reactivity of aliphatic carbon-sulfur bonds. When two dithioacetal functionalities are located in close proximity, selective olefination of one of these two dithioacetal groups can thus be achieved conveniently. Depending on the relative positions of the newly formed double bond and the remaining dithioacetal group, tandem olefination occurs to give the corresponding 1,5-bis-silyl-substituted pentadienes. Various neighboring heteroatom substituents (OR, OH, NR(2) as well as SR groups) can facilitate the olefination of a dithioacetal group. Poly(thioether) linkage afforded the corresponding degradation products via a B-sulfur elimination process. 1,3-Dimercapto- and 1,3-dithiolatopropanes furnish the cyclopropane formation under nickel-catalyzed reaction conditions. The reaction of a dihydrothiopyran with MeMgI in the presence of the nickel catalyst proceeds via a sulfur-coordinated ir-allyl complex, which can further activate the CS bond to give vinylcyclopropane.
• Synthesis of Medium Ring Disulfides by Titrimetry; An Improvement on High Dilution Techniques
  作者：Marvin H. Goodrow、W. Kenneth Musker

  DOI：10.1055/s-1981-29481

  日期：——