(Z)-4,4-bis(benzyloxymethyl)-2-ethylidene-1-methylcyclopentanecarbaldehyde | 1256270-28-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (Z)-4,4-bis(benzyloxymethyl)-2-ethylidene-1-methylcyclopentanecarbaldehyde
• 英文别名: (2Z)-2-ethylidene-1-methyl-4,4-bis(phenylmethoxymethyl)cyclopentane-1-carbaldehyde
• CAS: 1256270-28-6
• 化学式: C₂₅H₃₀O₃
• 分子量: 378.511
• InChiKey: WMXZYDVBCUUBNT-LNQJRUQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,4-bis(benzyloxymethyl)-2-methyloct-6-ynal 在 indium(III) chloride 、 环己胺 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 、 水 为溶剂， 反应 15.25h， 以68%的产率得到(Z)-4,4-bis(benzyloxymethyl)-2-ethylidene-1-methylcyclopentanecarbaldehyde
  参考文献：
  名称：

  InCl₃/CyNH₂ Cocatalyzed Carbocyclization Reaction: An Entry to α-Disubstituted exo-Methylene Cyclopentanes

  摘要：

  An efficient and cheap synthetic approach to functionalized exo-methylene cyclopentanes has been developed from alpha-disubstituted formyl-alkynes by merging amine catalysis with the indium activation of alkynes. We uncovered the crucial role of the amine cocatalyst and the development of a new cooperative catalytic system allowed the cyclization of a broad range of substrates. A mechanistic study was realized in order to rationalize the determining influence of the amine cocatalyst.

  DOI：

  10.1021/jo1018552

文献信息

• InCl₃/CyNH₂ Cocatalyzed Carbocyclization Reaction: An Entry to α-Disubstituted <i>exo</i>-Methylene Cyclopentanes
  作者：Benjamin Montaignac、Maxime R. Vitale、Virginie Ratovelomanana-Vidal、Véronique Michelet

  DOI：10.1021/jo1018552

  日期：2010.12.3

  An efficient and cheap synthetic approach to functionalized exo-methylene cyclopentanes has been developed from alpha-disubstituted formyl-alkynes by merging amine catalysis with the indium activation of alkynes. We uncovered the crucial role of the amine cocatalyst and the development of a new cooperative catalytic system allowed the cyclization of a broad range of substrates. A mechanistic study was realized in order to rationalize the determining influence of the amine cocatalyst.