2-[6-[(E)-3-ethoxy-3-oxoprop-1-enyl]-2,3-dimethoxyphenyl]acetic acid | 1215037-58-3

• 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-[6-[(E)-3-ethoxy-3-oxoprop-1-enyl]-2,3-dimethoxyphenyl]acetic acid
• CAS: 1215037-58-3
• 化学式: C₁₅H₁₈O₆
• 分子量: 294.304
• InChiKey: BCNLIKXZEFHDDH-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-二甲氧基苯乙酸 、 丙烯酸乙酯 在 N-乙酰-L-异亮氨酸 、 氧气 、 palladium diacetate 、 potassium hydrogencarbonate 作用下， 以 2-甲基-2-丁醇 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以95%的产率得到2-[6-[(E)-3-ethoxy-3-oxoprop-1-enyl]-2,3-dimethoxyphenyl]acetic acid
  参考文献：
  名称：

  Ligand-Accelerated C−H Activation Reactions: Evidence for a Switch of Mechanism

  摘要：

  Initial rate studies have revealed dramatic acceleration in aerobic Pd(II)-catalyzed C-H olefination reactions of phenylacetic acids when mono-N-protected amino acids are used as ligands. In light of these findings, systematic ligand tuning was undertaken, which has resulted in drastic improvements in substrate scope, reaction rate, and catalyst turnover. We present evidence from intermolecular competition studies and kinetic isotope effect experiments that implies that the observed rate increases are a result of acceleration in the C-H cleavage step. Furthermore, these studies suggest that the origin of this phenomenon is a change in the mechanism of C-H cleavage from electrophilic palladation to proton abstraction.

  DOI：

  10.1021/ja105044s

文献信息

• Ligand-Accelerated C−H Activation Reactions: Evidence for a Switch of Mechanism
  作者：Keary M. Engle、Dong-Hui Wang、Jin-Quan Yu

  DOI：10.1021/ja105044s

  日期：2010.10.13

  Initial rate studies have revealed dramatic acceleration in aerobic Pd(II)-catalyzed C-H olefination reactions of phenylacetic acids when mono-N-protected amino acids are used as ligands. In light of these findings, systematic ligand tuning was undertaken, which has resulted in drastic improvements in substrate scope, reaction rate, and catalyst turnover. We present evidence from intermolecular competition studies and kinetic isotope effect experiments that implies that the observed rate increases are a result of acceleration in the C-H cleavage step. Furthermore, these studies suggest that the origin of this phenomenon is a change in the mechanism of C-H cleavage from electrophilic palladation to proton abstraction.