5-Vinyl-nona-1,8-diene | 161485-21-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 5-Vinyl-nona-1,8-diene
• 英文别名: 5-Ethenylnona-1,8-diene
• CAS: 161485-21-8
• 化学式: C₁₁H₁₈
• 分子量: 150.264
• InChiKey: NUMQRZCQAZVWLA-UHFFFAOYSA-N

物化性质

• 沸点：
  190.4±20.0 °C(Predicted)
• 密度：
  0.767±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  5-Vinyl-nona-1,8-diene 在 叔丁基过氧化氢 、 Cp*₂Y(Me)(thf) 、 potassium hydride 作用下， 以 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (2S,4aS,8aS)-1-(Decahydro-naphthalen-2-yl)-methanol
  参考文献：
  名称：

  Stereoselective Synthesis of Carbobicyclics via Organoyttrium-Catalyzed Sequential Cyclization/Silylation Reactions

  摘要：

  The sequential cyclization/silylation of 1,5-dienes and 1,6-dienes was effected under mild reaction conditions using catalytic quantities of Cp-2*YMe . THF. The process provides carbobicyclics in high yields and with excellent selectivities. The active catalyst is postulated to be Cp-2*YH . THF, which is generated in situ. A variety of alkenyl-substituted cyclopentane and cyclohexane substrates were examined. The high diastereoselectivities apparently originate fi om a preference for a chairlike transition structure that minimizes unfavorable steric interactions between the bulky Cp* ligands of the catalyst and the preexisting ring of the substrate. Acyclic triene precursors, 4-ethenyl-substituted 1,5-heptadienes and 5-ethenyl-substituted 1,8-nonadienes were also examined. These triene substrates, when exposed to the cyclization/silylation protocol, provide the strained trans-bicyclo[3.3.0]octanes and trans-decalin systems in high yield with excellent diastereoselectivity. The high selectivity is again attributed to the preference for a chairlike transition structure. The cyclized organosilane products isolated from these reactions were easily converted to the more versatile alcohols utilizing known oxidation methods.

  DOI：

  10.1021/jo9721352
• 作为产物：
  描述：

  5-iodo-1,8-nonadiene 、 alkaline earth salt of/the/ methylsulfuric acid 生成 5-Vinyl-nona-1,8-diene
  参考文献：
  名称：

  Titanium-Catalyzed Cascade Carboalumination of Dienes and Trienes

  摘要：

  DOI：

  10.1021/ja00097a073

文献信息

• Negishi Eiichi, Jensen Michael D., Kondakov Denis Y., Wang Shan, J. Amer. Chem. Soc, 116 (1994) N 18, S 8404-8405
  作者：Negishi Eiichi, Jensen Michael D., Kondakov Denis Y., Wang Shan

  DOI：——

  日期：——
• Titanium-Catalyzed Cascade Carboalumination of Dienes and Trienes
  作者：E. Negishi、Michael D. Jensen、Denis Y. Kondakov、Shan Wang

  DOI：10.1021/ja00097a073

  日期：1994.9
• Stereoselective Synthesis of Carbobicyclics via Organoyttrium-Catalyzed Sequential Cyclization/Silylation Reactions
  作者：Gary A. Molander、Paul J. Nichols、Bruce C. Noll

  DOI：10.1021/jo9721352

  日期：1998.4.1

  The sequential cyclization/silylation of 1,5-dienes and 1,6-dienes was effected under mild reaction conditions using catalytic quantities of Cp-2*YMe . THF. The process provides carbobicyclics in high yields and with excellent selectivities. The active catalyst is postulated to be Cp-2*YH . THF, which is generated in situ. A variety of alkenyl-substituted cyclopentane and cyclohexane substrates were examined. The high diastereoselectivities apparently originate fi om a preference for a chairlike transition structure that minimizes unfavorable steric interactions between the bulky Cp* ligands of the catalyst and the preexisting ring of the substrate. Acyclic triene precursors, 4-ethenyl-substituted 1,5-heptadienes and 5-ethenyl-substituted 1,8-nonadienes were also examined. These triene substrates, when exposed to the cyclization/silylation protocol, provide the strained trans-bicyclo[3.3.0]octanes and trans-decalin systems in high yield with excellent diastereoselectivity. The high selectivity is again attributed to the preference for a chairlike transition structure. The cyclized organosilane products isolated from these reactions were easily converted to the more versatile alcohols utilizing known oxidation methods.