6-(benzyloxy)hex-1-en-4-yne | 172788-00-0

• 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)hex-1-en-4-yne
• 英文别名: Hex-5-en-2-ynoxymethylbenzene
• CAS: 172788-00-0
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: PNCNWXKASNZTRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(benzyloxy)hex-1-en-4-yne 在 硫脲 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 6-(benzyloxy)-1,2-epithio-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
• 作为产物：
  描述：

  苄基丙炔基醚 、 3-溴丙烯 在 copper(l) iodide 、 甲基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.0h， 以85%的产率得到6-(benzyloxy)hex-1-en-4-yne
  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

• CO2(CO)8-Assisted synthesis of propargylic unsymmetrical ethers by reaction of alcohols with propargylic alcohols
  作者：David D Dı́az、Victor S Martı́n

  DOI：10.1016/s0040-4039(00)01756-1

  日期：2000.12

  propargylic ethers after cobalt demetallation. The procedure is highly effective for the preparation of symmetrical and unsymmetrical ethers derived from primary alcohols and primary and secondary propargylic alcohols. The method permits the use of a wide range of alcohols including those having halogens in their structures.

  钴脱金属后，用CO 2（CO）6-丙炔醇对醇进行路易斯酸处理，得到丙炔醚。该方法对于制备衍生自伯醇以及伯和仲炔丙醇的对称和不对称醚非常有效。该方法允许使用多种醇，包括在其结构中具有卤素的醇。
• 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.