cis-2,5-Di-brommethyl-thiophan | 89791-59-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: cis-2,5-Di-brommethyl-thiophan
• 英文别名: (2R,5S)-2,5-bis(bromomethyl)thiolane
• CAS: 89791-59-3
• 化学式: C₆H₁₀Br₂S
• 分子量: 274.019
• InChiKey: FGHKXTDGDXVTSS-OLQVQODUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,2-环硫-5-己烯 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 cis-2,5-Di-brommethyl-thiophan 、 (2S,5R)-5-Bromo-2-bromomethyl-tetrahydro-thiopyran
  参考文献：
  名称：

  Regiochemical and stereochemical studies on halogen-induced ring expansions of unsaturated episulfides

  摘要：

  The reactions of unsaturated episulfides with bromine and iodine have been studied. Initially produced in the reaction is a ring opened sulfenyl halide intermediate, which in the presence of the carbon-carbon double bond or triple bond cyclizes to beta,beta'-dihalo sulfide cycloadducts. The regiochemistry and relative stereochemistry of these cyclizations have been examined as a function of the length of the tether between the episulfide moiety and the unsaturated functionality, the presence of alkyl substituents, and the type of unsaturation. A discussion of the mechanistic and stereochemical features of the ring-expansion process is presented.

  DOI：

  10.1021/jo00125a039