(E)-3-Phenyl-pent-2-enethioic acid methyl-phenyl-amide | 176715-87-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-3-Phenyl-pent-2-enethioic acid methyl-phenyl-amide
• CAS: 176715-87-0
• 化学式: C₁₈H₁₉NS
• 分子量: 281.422
• InChiKey: OFOOFSSDOMSEAO-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-3-Phenyl-pent-2-enethioic acid methyl-phenyl-amide 反应 95.0h， 以23%的产率得到(Z)-3-Phenyl-pent-2-enethioic acid methyl-phenyl-amide
  参考文献：
  名称：

  EZ-Isomerization of α,β-punsaturated Acid Derivatives in the Solid State

  摘要：

  The solid-state EZ-isomerizability of alpha,beta-unsaturated amide was greatly improved by modifying their structure, which had low isomerizability in the solid state; EZ-isomerizability was attained by replacing the carbonyl group of the amides by a thiocarbonyl group as well as replacing the heterochiral N-substituent of the amides by a homochiral one. Furthermore, EZ-photoisomerization was also attained for several kinds of salts of alpha,beta-unsaturated carboxylic acids with amines. This photoreaction was proven to be an effective method for preparing (Z)-isomers from ammonium (E)-alpha,beta-unsaturated carboxylates. The isomerizability was strikingly altered upon changing the ammonium part, which implied that the crystal structure affected the reactivity to a considerable extent. A further detailed study concerning the crystal structures suggested that the characteristic of the hydrogen-bond network had a close correlation with the isomerizability. Moreover, both the bulkiness of the carboxylate and ammonium parts as well as their difference in length were considered to be the most important factors influencing the isomerizability.

  DOI：

  10.1080/10587259608039371
• 作为产物：
  描述：

  3-phenyl-pent-2-enoyl chloride 在 劳森试剂 、 吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 (E)-3-Phenyl-pent-2-enethioic acid methyl-phenyl-amide
  参考文献：
  名称：

  固态α,β-不饱和酰胺和硫代酰胺的光化学EZ-异构化

  摘要：

  α,β-不饱和酰胺在固态时的异构化能力较低，通过对其结构进行修饰，其固态EZ异构化能力得到了极大的提高；EZ-异构化是通过用硫代羰基取代酰胺的羰基以及用同手性取代酰胺的杂手性N-取代基来实现的。晶体学分析表明，固态的 α,β-不饱和酰胺和硫代酰胺的异构化部分取决于它们在晶体中的分子构象。此外，发现填充系数与异构化能力相关；较小的填充系数值会导致 (Z)-异构体的形成增加。

  DOI：

  10.1246/bcsj.69.779