6-(benzyloxy)-1,2-epoxy-4-hexyne | 172788-01-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(benzyloxy)-1,2-epoxy-4-hexyne
• 英文别名: 2-(4-Phenylmethoxybut-2-ynyl)oxirane
• CAS: 172788-01-1
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: BPFDNJWEWDXVSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(benzyloxy)-1,2-epoxy-4-hexyne 在 碘 、 硫脲 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 5-<(benzyloxy)methyl>-2,3-dihydro-4-iodo-2-(iodomethyl)thiophene
  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
• 作为产物：
  描述：

  苄基丙炔基醚 在 copper(l) iodide 、 甲基溴化镁 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 6-(benzyloxy)-1,2-epoxy-4-hexyne
  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

文献信息

• Regiochemical and stereochemical studies on halogen-induced ring expansions of unsaturated episulfides
  作者：Xiao-Feng Ren、Monika I. Konaklieva、Edward Turos、Lynn M. Krajkowski、Charles H. Lake、Thomas S. Janik、Melvyn Rowen Churchill

  DOI：10.1021/jo00125a039

  日期：1995.10

  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.