(E)-2-(3,4,5-trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxo-2-butenoic acid | 158979-65-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-2-(3,4,5-trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxo-2-butenoic acid
• CAS: 158979-65-8
• 化学式: C₂₀H₁₈O₈
• 分子量: 386.358
• InChiKey: WBGMOLLTYLTJPZ-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 (E)-2-(3,4,5-trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxo-2-butenoic acid 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以96.2%的产率得到methyl (E)-2-(3,4,5-trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxo-2-butenoic acid
  参考文献：
  名称：

  Photochemistry of 2-(3,4,5-trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxo-2-butenonitrile (β-cyanochalcone) and its related compounds

  摘要：

  Photochemistry of the titled compounds both in solid state and in solution is described. The (Z)-isomers of beta-substituted chalcones (5, 8 and 9) mainly dimerized into topochemically favored single cyclobutane dimers (10, 14 and 13) in solid state photoreactions, while in solution those isomerized into the corresponding (E)-isomers. Interestingly exposure of the (E)-isomer (5E) of beta-cyanochalcone to sunlight in the solid state led to unusual dimerization through isomerization to give an unsymmetrical (E-Z)-dimer (11) along with a symmetrical (Z-Z)-dimer (10) obtainable from the photoreactive (Z)-isomer (5Z-b). The photochemical reactivities of the esters (9) are discussed based on their crystal structures.

  DOI：

  10.1016/s0040-4020(01)85506-x
• 作为产物：
  描述：

  4-(3,4-methylenedioxyphenyl)-4-oxo-2-(3,4,5-trimethoxyphenyl)butyronitrile 在 sodium hydroxide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 丙酮 、 苯 为溶剂， 反应 91.0h， 生成 (E)-2-(3,4,5-trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxo-2-butenoic acid
  参考文献：
  名称：

  Photochemistry of 2-(3,4,5-trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxo-2-butenonitrile (β-cyanochalcone) and its related compounds

  摘要：

  Photochemistry of the titled compounds both in solid state and in solution is described. The (Z)-isomers of beta-substituted chalcones (5, 8 and 9) mainly dimerized into topochemically favored single cyclobutane dimers (10, 14 and 13) in solid state photoreactions, while in solution those isomerized into the corresponding (E)-isomers. Interestingly exposure of the (E)-isomer (5E) of beta-cyanochalcone to sunlight in the solid state led to unusual dimerization through isomerization to give an unsymmetrical (E-Z)-dimer (11) along with a symmetrical (Z-Z)-dimer (10) obtainable from the photoreactive (Z)-isomer (5Z-b). The photochemical reactivities of the esters (9) are discussed based on their crystal structures.

  DOI：

  10.1016/s0040-4020(01)85506-x

文献信息

• Photochemistry of 2-(3,4,5-trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxo-2-butenonitrile (β-cyanochalcone) and its related compounds
  作者：Tsutomu Ishikawa、Nobuyuki Koseki、Tomoko Furukawa、Eri Sakurada (nee Kawanabe)、Chiharu Koseki、Yuki Saito、Koreharu Ogata、Takashi Harayama、Hisashi Ishii

  DOI：10.1016/s0040-4020(01)85506-x

  日期：——

  Photochemistry of the titled compounds both in solid state and in solution is described. The (Z)-isomers of beta-substituted chalcones (5, 8 and 9) mainly dimerized into topochemically favored single cyclobutane dimers (10, 14 and 13) in solid state photoreactions, while in solution those isomerized into the corresponding (E)-isomers. Interestingly exposure of the (E)-isomer (5E) of beta-cyanochalcone to sunlight in the solid state led to unusual dimerization through isomerization to give an unsymmetrical (E-Z)-dimer (11) along with a symmetrical (Z-Z)-dimer (10) obtainable from the photoreactive (Z)-isomer (5Z-b). The photochemical reactivities of the esters (9) are discussed based on their crystal structures.