8-methylene-1,4-dithia-spiro[4.5]decane | 54531-72-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 8-methylene-1,4-dithia-spiro[4.5]decane
• 英文别名: 8-Methylidene-1,4-dithiaspiro[4.5]decane
• CAS: 54531-72-5
• 化学式: C₉H₁₄S₂
• 分子量: 186.342
• InChiKey: QTYBGFBZLBKSEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲基碘化镁 、 1,4-cyclohexanedione diethylenethioacetal 在 bis(triphenylphosphine)nickel(II) chloride 作用下， 以 乙醚 、 苯 为溶剂， 生成 8-methylene-1,4-dithia-spiro[4.5]decane 、 8-Methyl-1,4-dithia-spiro[4.5]dec-7-ene
  参考文献：
  名称：

  A chelation approach toward activation of Csp3-S bonds. Nickel-catalyzed selective cross coupling of bisdithioacetals with Grignard reagents

  摘要：

  DOI：

  10.1021/ja00044a060

文献信息

• A chelation approach toward activation of Csp3-S bonds. Nickel-catalyzed selective cross coupling of bisdithioacetals with Grignard reagents
  作者：Ken Tsung Wong、Tien Yau Luh

  DOI：10.1021/ja00044a060

  日期：1992.8
• 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.