(Z)-3-(4-methoxyphenyl)acrylamide | 1194827-03-6

• 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: (Z)-3-(4-methoxyphenyl)acrylamide
• 英文别名: 4-methoxy-cis-cinnamic acid amide；4-Methoxy-cis-zimtsaeure-amid；(2Z)-3-(4-Methoxyphenyl)-2-propenamide；(Z)-3-(4-methoxyphenyl)prop-2-enamide
• CAS: 1194827-03-6
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: LQGHBKPIJSBKEY-DAXSKMNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙醚 、 (Z)-3-(4-methoxyphenyl)acrylamide 、 溴 生成 4-methoxycinnamic acid amide
  参考文献：
  名称：

  Stoermer, Chemische Berichte, 1911, vol. 44, p. 644

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 (Z)-3-(4-methoxyphenyl)acrylamide
  参考文献：
  名称：

  Stoermer; Wodarg, Chemische Berichte, 1928, vol. 61, p. 2328

  摘要：

  DOI：

文献信息

• Photocatalyst-free visible light promoted <i>E</i> → <i>Z</i> isomerization of alkenes
  作者：Jianbin Xu、Na Liu、Haiping Lv、Chixian He、Zining Liu、Xianfu Shen、Feixiang Cheng、Baomin Fan

  DOI：10.1039/c9gc04303a

  日期：——

  A simple and green method of visible light driven photocatalytic E to Z isomerization of alkenes has been developed. A variety of (Z)-alkenes can be prepared in the presence of visible light, without any additional photocatalyst. This protocol features photocatalyst-free conditions, which are mild, tolerant, and operationally simple, and is easy to implement.

  一个简单而驱动光催化可见光的绿色方法Ë到ž烯烃异构化已经研制成功。可以在可见光存在下制备各种（Z）烯烃，而无需任何其他光催化剂。该协议具有无光催化剂的条件，该条件温和，宽容且操作简单，易于实施。
• Configuration-dependent photoisomerization of (E)-cinnamamides
  作者：Frederick D. Lewis、Jeffrey E. Elbert、Alana L. Upthagrove、Paul D. Hale

  DOI：10.1021/ja00223a048

  日期：1988.7

  Effets des substituants de l'azote et du cycle benzenique sur la photoisomerisation dans l'UV proche des composes ci-dessus

  Effets des substituants de l'azote et du cycle benzenique sur la photoisomerisation dans l'UV proche des composes ci-dessus
• Lewis-acid catalysis of photochemical reactions. 9. Structure and photoisomerization of (E)- and (Z)-cinnamamides and their Lewis acid complexes
  作者：Frederick D. Lewis、Jeffrey E. Elbert、Alana L. Upthagrove、Paul D. Hale

  DOI：10.1021/jo00002a015

  日期：1991.1

  The spectroscopic properties and photoisomerization reactions of several (E)- and (Z)-cinnamamides have been investigated in the absence and presence of the strong Lewis acid BF3. The (E)-cinnamamides are essentially planar and exist predominantly in the enone s-cis conformation, except in the case of the alpha-methyl tertiary amide which adopts the s-trans conformation in order to minimize nonbonded repulsion. The (Z)-cinnamamides exist predominantly in the highly nonplanar s-trans conformation. This unusual conformational preference is attributed to intramolecular charge transfer from the aromatic to amide functionality. Photoisomerization efficiencies are dependent upon N-alkylation, aromatic substitution, alpha-alkylation, solvent, and excitation wavelength. These effects are attributed to the existence of two lowest energy pi,pi* singlet states (one reactive and one nonreactive) whose relative energies are dependent upon substitution. The cinnamamides from 1:1 complexes with BF3 with equilibrium constants > 10(3). Complexation alters both the electronic structure and photochemical behavior of the cinnamamides. Quantitative E --> Z isomerization has been observed for the BF3 complexes of two tertiary amides.
• LEWIS, FREDERICK D.;ELBERT, JEFFREY E.;UPTHAGROVE, ALANA L.;HALE, PAUL D., J. AMER. CHEM. SOC., 110,(1988) N 15, 5191-5192
  作者：LEWIS, FREDERICK D.、ELBERT, JEFFREY E.、UPTHAGROVE, ALANA L.、HALE, PAUL D.

  DOI：——

  日期：——