(E)-2-(3,4,5-trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxo-2-butenonitrile | 138037-36-2

• 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-butenonitrile
• 英文别名: (E)-2-(3,4,5-trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxobutenonitrile；(E)-4-(1,3-benzodioxol-5-yl)-4-oxo-2-(3,4,5-trimethoxyphenyl)but-2-enenitrile
• CAS: 138037-36-2
• 化学式: C₂₀H₁₇NO₆
• 分子量: 367.358
• InChiKey: GFEOXXFKMYRVGX-NSIKDUERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-2-(3,4,5-trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxo-2-butenonitrile 以 甲醇 为溶剂， 反应 12.0h， 生成 1,t-2-bis(3,4,5-trimethoxyphenyl)-c-3,c-4-bis(3,4-methylenedioxybenzoyl)-r-1,c-2-cyclobutanedinitrile
  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 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 42.5h， 生成 (E)-2-(3,4,5-trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxo-2-butenonitrile
  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

• "Studies on the chemical constituents of rutaceous plants." Part 71. Photochemistry of 2-(3,4,5-trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxo-2-butenonitrile(.BETA.-cyanochalcone): Anomalous dimerization through isomerization in the solid state.
  作者：Hisashi ISHII、Eri SAKURADA、Tomoko FURUKAWA、Chiharu KOSEKI、Koreharu OGATA、Nobuyuki KOSEKI、Tsutomu ISHIKAWA、Takashi HARAYAMA

  DOI：10.1248/cpb.39.2173

  日期：——

  Exposure of the (E)-isomer (4E) of 2-(3, 4, 5-trimethoxyphenyl)-4-(3, 4-methylenedioxyphenyl)-4-oxo-2-butenonitrile (β-cyanochalcone) in the solid state to sunlight led to unusual dimerization through isomerization to give an unsymmetrical E-Z dimer (7) along with a symmetrical Z-Z dimer (5) obtainable from the photoreactive (Z)-isomer (4Z-b).

  将固态的 2-(3,4,5-三甲氧基苯基)-4-(3,4-亚甲基二氧苯基)-4-氧代-2-丁烯腈（β-氰基查尔酮）的(E)-异构体(4E)暴露在阳光下，通过异构化产生了不对称的 E-Z 二聚体(7)，同时从光活性(Z)-异构体(4Z-b)中得到了对称的 Z-Z 二聚体(5)。
• 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.