(3E,7Z)-4-methyldeca-3,7-dien-1-ol | 955013-32-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3E,7Z)-4-methyldeca-3,7-dien-1-ol
• CAS: 955013-32-8
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: AKUBJVNQYOKBBF-JHGYFVHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3E,7Z)-4-methyldeca-3,7-dien-1-ol 在 (dppe)PtI₂ silver tetrafluoroborate 作用下， 以 various solvent(s) 为溶剂， 反应 12.0h， 以72%的产率得到(3aS,4S,7aS)-4-ethyl-7a-methyl-3,3a,4,7-tetrahydro-2H-1-benzofuran
  参考文献：
  名称：

  Regioselective Oxidative Cation-Olefin Cyclization of Poly-enes:  Catalyst Turnover via Hydride Abstraction

  摘要：

  Electrophilic P2Pt2+ complexes are shown to catalyze the regio- and diastereoselective oxidative cascade cyclization of poly-enes. The reactions are stereospecific with respect to the initiating alkenes geometry and suggest an all-chair, semiconcerted transition structure. Catalyst turnover after cyclization apparently occurs via beta-hydride elimination and subsequent hydride abstraction (from P2Pt-H+) by added Trityl cation (in the form of trityl methyl ether or a resin version thereof) to regenerate the active P(2)pt(2+) state. One intriguing possibility is that the high regioselectivity observed in the beta-H elimination is due to a regio-defining beta-agostic resting state.

  DOI：

  10.1021/ja073573l
• 作为产物：
  描述：

  C₁₀H₁₆O 、 甲基溴化镁 在 bis(triphenylphosphine)nickel(II) chloride 作用下， 以 乙醚 、 甲苯 为溶剂， 以56%的产率得到(3E,7Z)-4-methyldeca-3,7-dien-1-ol
  参考文献：
  名称：

  Regioselective Oxidative Cation-Olefin Cyclization of Poly-enes:  Catalyst Turnover via Hydride Abstraction

  摘要：

  Electrophilic P2Pt2+ complexes are shown to catalyze the regio- and diastereoselective oxidative cascade cyclization of poly-enes. The reactions are stereospecific with respect to the initiating alkenes geometry and suggest an all-chair, semiconcerted transition structure. Catalyst turnover after cyclization apparently occurs via beta-hydride elimination and subsequent hydride abstraction (from P2Pt-H+) by added Trityl cation (in the form of trityl methyl ether or a resin version thereof) to regenerate the active P(2)pt(2+) state. One intriguing possibility is that the high regioselectivity observed in the beta-H elimination is due to a regio-defining beta-agostic resting state.

  DOI：

  10.1021/ja073573l