Di-(Z)-hex-4-enyl diselenide | 154414-58-1

• 分子结构分类: 有机化合物 - 有机金属化合物
• 英文名称: Di-(Z)-hex-4-enyl diselenide
• 英文别名: (Z)-6-[[(Z)-hex-4-enyl]diselanyl]hex-2-ene
• CAS: 154414-58-1
• 化学式: C₁₂H₂₂Se₂
• 分子量: 324.227
• InChiKey: WVOJLABSFFKCNQ-GLIMQPGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  Di-(Z)-hex-4-enyl diselenide 在 lithium aluminium tetrahydride 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 cis-4-Chloro-3-methylselenacycloheptane
  参考文献：
  名称：

  A New Method of Generation of .alpha.-Selenocarbenium Ions from Se,O-Heteroacetals and Their Reactions

  摘要：

  Various Se,O-heteroacetals were prepared by the LiAlH4 reduction of diselenides 1 followed by alkylation with methoxymethyl chloride or (2-methoxyethoxy)methyl (MEM) chloride. Olefinic and acetylenic alpha-seleno carbenium ions were generated by the selective C-O bond cleavage of O-(2-methoxyethyl)-Se,O-heteroacetals with titanium(IV) chloride and cyclized to give the seleno heterocyclic compounds. Olefinic MEM-selenides 3a,b,d-f,h underwent the endo-mode cyclization to afford 4-chloroselenacycloalkanes 4a,b,d-f,h in good yields, whereas acetylenic MEM-selenides 12b-e,g-j underwent the exo-mode cyclization to give 3-(1-chloroalkylidene)selenacycloalkanes 13b-e,g-j. This new utilization of alpha-seleno carbenium ions was also applied to the intramolecular and intermolecular Friedel-Crafts reactions.

  DOI：

  10.1021/jo00084a017
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 selenium 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 Di-(Z)-hex-4-enyl diselenide
  参考文献：
  名称：

  A New Method of Generation of .alpha.-Selenocarbenium Ions from Se,O-Heteroacetals and Their Reactions

  摘要：

  Various Se,O-heteroacetals were prepared by the LiAlH4 reduction of diselenides 1 followed by alkylation with methoxymethyl chloride or (2-methoxyethoxy)methyl (MEM) chloride. Olefinic and acetylenic alpha-seleno carbenium ions were generated by the selective C-O bond cleavage of O-(2-methoxyethyl)-Se,O-heteroacetals with titanium(IV) chloride and cyclized to give the seleno heterocyclic compounds. Olefinic MEM-selenides 3a,b,d-f,h underwent the endo-mode cyclization to afford 4-chloroselenacycloalkanes 4a,b,d-f,h in good yields, whereas acetylenic MEM-selenides 12b-e,g-j underwent the exo-mode cyclization to give 3-(1-chloroalkylidene)selenacycloalkanes 13b-e,g-j. This new utilization of alpha-seleno carbenium ions was also applied to the intramolecular and intermolecular Friedel-Crafts reactions.

  DOI：

  10.1021/jo00084a017