1,t-2-bis(3,4,5-trimethoxyphenyl)-c-3,c-4-bis(3,4-methylenedioxybenzoyl)-r-1,c-2-cyclobutanedinitrile | 138037-38-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 环丁烷木脂素
• 英文名称: 1,t-2-bis(3,4,5-trimethoxyphenyl)-c-3,c-4-bis(3,4-methylenedioxybenzoyl)-r-1,c-2-cyclobutanedinitrile
• 英文别名: (1S,2R,3S,4R)-3,4-bis(1,3-benzodioxole-5-carbonyl)-1,2-bis(3,4,5-trimethoxyphenyl)cyclobutane-1,2-dicarbonitrile
• CAS: 138037-38-4
• 化学式: C₄₀H₃₄N₂O₁₂
• 分子量: 734.716
• InChiKey: LJRYNXRESZYJMG-JNYDDLKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  54
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  174
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1,t-2-bis(3,4,5-trimethoxyphenyl)-c-3,c-4-bis(3,4-methylenedioxybenzoyl)-r-1,c-2-cyclobutanedinitrile 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以86.8%的产率得到1,t-2-bis(3,4,5-trimethoxyphenyl)-c-3,t-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 solid 为溶剂， 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：

  "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.

  摘要：

  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)。

  DOI：

  10.1248/cpb.39.2173