deuteriated cinnamic acid | 112486-68-7

• 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: deuteriated cinnamic acid
• 英文别名: α,β-Dideuterio-trans-cinnamic acid；α,β-Dideuterio-cis-cinnamic acid；α,β-Dideuterio-cis-zimtsaeure；α,β-Dideutero-cis-zimtsaeure；(Z)-2,3-dideuterio-3-phenyl-acrylic acid
• CAS: 112486-68-7；122570-76-7
• 化学式: C₉H₈O₂
• 分子量: 150.145
• InChiKey: WBYWAXJHAXSJNI-RFLMMHNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  苯丙炔酸乙酯 在 Lindlar's catalyst 喹啉 、 sodium hydroxide 、 氘 作用下， 以 乙醇 、 正己烷 为溶剂， 反应 9.0h， 生成 deuteriated cinnamic acid
  参考文献：
  名称：

  Influence of nucleophiles on the high-temperature aqueous isomerization of cis- to trans-cinnamic acid

  摘要：

  The rate of isomerization of cis- to trans-cinnamic acid in water at 195-degrees-C was monitored as a function of added nucleophile. The expected nucleophile addition products were not observed but could be synthesized and, when subjected to the reaction conditions, rapidly converted to trans-cinnamic acid. Deuterium labeling studies indicated that proton abstraction was not the rate-determining step, that the alpha-deuterium of alpha,beta-dideuterio-cis-cinnamic acid was rapidly exchanged for an alpha-hydrogen atom without loss of the cis geometry, and that some direct isomerization of cis- to trans-cinnamic acid occurred without the loss of vinyl deuterium atoms. The isomerization appears to involve an addition-elimination mechanism in the case of HO- and HS- ions, with the former more effective. Anthrahydroquinone ion was quite effective, meaning that it was a superior nucleophile or was promoting reactions by another mechanism (possibly electron transfer chemistry). The results have bearing on the rate-determining step in one of the delignification mechanisms occurring during the pulping of wood.

  DOI：

  10.1021/jo00075a034