2-(4-methylcyclohex-3-en-1-yl)propan-2-yl cinnamate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-(4-methylcyclohex-3-en-1-yl)propan-2-yl cinnamate
• 英文别名: 2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-yl (E)-3-phenylprop-2-enoate
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: CKYQZYGVFMSSKH-WKOYGUFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (R)-2-(4-methylcyclohex-3-en-1-yl)propan-2-yl 3-phenylpropanoate 在 正丁基锂 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 zinc(II) chloride 、 bis(η3-allyl-μ-chloropalladium(II)) 、 allyl t-butyl carbonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.0h， 以78%的产率得到2-(4-methylcyclohex-3-en-1-yl)propan-2-yl cinnamate
  参考文献：
  名称：

  Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles

  摘要：

  A highly practical and general palladium-catalyzed methodology for the alpha,beta-dehydrogenation of esters and nitriles is repotted. Generation of a zinc enolate or (cyanoalkyl)zinc species followed by the addition of an allyl oxidant and a palladium catalyst results in synthetically useful yields of alpha,beta-unsaturated esters, lactones, and nitriles. Preliminary mechanistic investigations are consistent with reversible beta-hydride elimination and turnover-limiting, propene-forming reductive elimination.

  DOI：

  10.1021/jacs.5b02243

文献信息

• Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles
  作者：Yifeng Chen、Justin P. Romaire、Timothy R. Newhouse

  DOI：10.1021/jacs.5b02243

  日期：2015.5.13

  A highly practical and general palladium-catalyzed methodology for the alpha,beta-dehydrogenation of esters and nitriles is repotted. Generation of a zinc enolate or (cyanoalkyl)zinc species followed by the addition of an allyl oxidant and a palladium catalyst results in synthetically useful yields of alpha,beta-unsaturated esters, lactones, and nitriles. Preliminary mechanistic investigations are consistent with reversible beta-hydride elimination and turnover-limiting, propene-forming reductive elimination.