2-<(3,3-dimethylcyclopentyl)methyl>-1,3-dithiane | 131545-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 2-<(3,3-dimethylcyclopentyl)methyl>-1,3-dithiane
• 英文别名: 2-[(3,3-Dimethylcyclopentyl)methyl]-1,3-dithiane
• CAS: 131545-93-2
• 化学式: C₁₂H₂₂S₂
• 分子量: 230.439
• InChiKey: QPPHHAZJDXLHSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2,2-二甲基-5-己烯-1-醇 在 吡啶 、 四甲基乙二胺 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 2-<(3,3-dimethylcyclopentyl)methyl>-1,3-dithiane
  参考文献：
  名称：

  Single electron transfer mechanism in the reaction of 1,3-dithianyllithium and alkyl iodides

  摘要：

  The reaction between 2-lithio-1,3-dithiane and optically active (R)-2-iodooctane was found to proceed with complete inversion of configuration. This result suggests that the S(N)2 (rather than single electron transfer (SET) mechanism is the preferred pathway for reaction between dithianyllithium and unhindered alkyl halides. When the neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene was used as the substrate halide, 6-11% cyclized alkylated product was obtained. This result suggests that when the S(N)2 pathway is blocked, SET mechanisms become operative to some extent, at least with iodide as the halogen. The reaction of dithianyllithium and (R)-2-iodooctane and 5,5-dimethyl-6-iodo-1-hexene, with hexane as the solvent, proceeds under heterogeneous conditions to bring about complete racemization or cyclization of the respective iodide. These results demonstrate for the first time that 2-lithio-1,3-dithiane can act as electron donor in reactions initiated by electron transfer to alkyl iodides.

  DOI：

  10.1021/jo00004a051

文献信息

• JUARISTI, EUSEBIO;JIMENEZ-VAZQUEZ, HUGO A., J. ORG. CHEM., 56,(1991) N, C. 1623-1630
  作者：JUARISTI, EUSEBIO、JIMENEZ-VAZQUEZ, HUGO A.

  DOI：——

  日期：——