(R,E)-1,8-diphenyloct-2-en-7-yn-1-ol | 1245902-13-9

• 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: (R,E)-1,8-diphenyloct-2-en-7-yn-1-ol
• 英文别名: (E,1R)-1,8-diphenyloct-2-en-7-yn-1-ol
• CAS: 1245902-13-9
• 化学式: C₂₀H₂₀O
• 分子量: 276.378
• InChiKey: NEKGZTIDNJPSQI-FVECTHPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (R,E)-1,8-diphenyloct-2-en-7-yn-1-ol 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium tert-butylate 、 三环己基膦 作用下， 以 甲苯 为溶剂， 生成 (R,E)-2-(2-benzylidenecyclopentyl)-1-phenylethanone 、 (S,E)-2-(2-benzylidenecyclopentyl)-1-phenylethanone
  参考文献：
  名称：

  Mechanistic Insights into Nickel-Catalyzed Cycloisomerizations

  摘要：

  A nickel-catalyzed cycloisomerization coupling an allylic alcohol with an alkyne has been developed Mechanistic insights gained through deuterium-labeling crossover studies and stereochemical probes illustrate that oxidation of the allylic alcohol to a metal-free enone is not involved in the cyclization pathway. The intermediacy of a metallacycle directly derived from oxidative cyclization of Ni(O) with the allylic alcohol and alkyne is consistent with the results obtained. The simple mechanistic probes employed could be useful in the study of many classes of cycloisomerization processes.

  DOI：

  10.1021/ol101852w
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 生成 (R,E)-1,8-diphenyloct-2-en-7-yn-1-ol
  参考文献：
  名称：

  Mechanistic Insights into Nickel-Catalyzed Cycloisomerizations

  摘要：

  A nickel-catalyzed cycloisomerization coupling an allylic alcohol with an alkyne has been developed Mechanistic insights gained through deuterium-labeling crossover studies and stereochemical probes illustrate that oxidation of the allylic alcohol to a metal-free enone is not involved in the cyclization pathway. The intermediacy of a metallacycle directly derived from oxidative cyclization of Ni(O) with the allylic alcohol and alkyne is consistent with the results obtained. The simple mechanistic probes employed could be useful in the study of many classes of cycloisomerization processes.

  DOI：

  10.1021/ol101852w