(E,E)-1,2-Bis(2-acetoxy-2-cyanoethenyl)benzene | 139131-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E,E)-1,2-Bis(2-acetoxy-2-cyanoethenyl)benzene
• 英文别名: [(E)-2-[2-[(E)-2-acetyloxy-2-cyanoethenyl]phenyl]-1-cyanoethenyl] acetate
• CAS: 139131-49-0
• 化学式: C₁₆H₁₂N₂O₄
• 分子量: 296.282
• InChiKey: IMUFFFIYLJBUAZ-BGPOSVGRSA-N

物化性质

• 沸点：
  466.4±45.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E,E)-1,2-Bis(2-acetoxy-2-cyanoethenyl)benzene 以 氘代氯仿 为溶剂， 反应 42.0h， 以18%的产率得到exo,exo-5,6-diacetoxy-5,6-dicyano-2,3-benzobicyclo<2.2.1>hex-2-ene
  参考文献：
  名称：

  Bis(2-acetoxyacrylonitrile) and its phenylene and alkylene bis homologs. Preparation, isomerization, and intramolecular [2 + 2] photocycloaddition

  摘要：

  The title compounds, 1,4-diacetoxy-1,4-dicyano-1,3-butadiene (3), 1,6-diacetoxy-1,6-dicyano-1,5-hexadiene (8), 1,2-bis(2-acetoxy-2-cyanovinyl)benzene (13), and 1,4-bis(2-acetoxy-2-cyanovinyl)benzene (17) were prepared by acetylation of the corresponding diacyl dicyanides. Dicyanides were prepared from diacyl chlorides by reaction with cyanotrimethylsilane or the NaI-Cu2(CN)2 reagent. Among the three geometrical isomers of the title compounds, the Z,Z diene predominated in 8 whereas E,E dienes predominated in conjugated dienes 3, 13, and 17. Conjugated E,E dienes underwent photoisomerization to E,Z and Z,Z isomers much faster than unconjugated diene 8. Prolonged irradiation on 13 yielded intramolecular [2 + 2] cycloadducts endo, exo- and exo,exo-5,6-diacetoxy-5,6-dicyano-2,3-benzobicyclo[2.1.1]hex-2-ene (22). Photochemistry in the formation of 22 is discussed.

  DOI：

  10.1021/jo00034a015
• 作为产物：
  描述：

  o-Phenylendiessigsaeure-dichlorid 在 吡啶 、 phosphorus pentoxide 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 74.0h， 生成 (E,E)-1,2-Bis(2-acetoxy-2-cyanoethenyl)benzene
  参考文献：
  名称：

  Bis(2-acetoxyacrylonitrile) and its phenylene and alkylene bis homologs. Preparation, isomerization, and intramolecular [2 + 2] photocycloaddition

  摘要：

  The title compounds, 1,4-diacetoxy-1,4-dicyano-1,3-butadiene (3), 1,6-diacetoxy-1,6-dicyano-1,5-hexadiene (8), 1,2-bis(2-acetoxy-2-cyanovinyl)benzene (13), and 1,4-bis(2-acetoxy-2-cyanovinyl)benzene (17) were prepared by acetylation of the corresponding diacyl dicyanides. Dicyanides were prepared from diacyl chlorides by reaction with cyanotrimethylsilane or the NaI-Cu2(CN)2 reagent. Among the three geometrical isomers of the title compounds, the Z,Z diene predominated in 8 whereas E,E dienes predominated in conjugated dienes 3, 13, and 17. Conjugated E,E dienes underwent photoisomerization to E,Z and Z,Z isomers much faster than unconjugated diene 8. Prolonged irradiation on 13 yielded intramolecular [2 + 2] cycloadducts endo, exo- and exo,exo-5,6-diacetoxy-5,6-dicyano-2,3-benzobicyclo[2.1.1]hex-2-ene (22). Photochemistry in the formation of 22 is discussed.

  DOI：

  10.1021/jo00034a015

文献信息

• Bis(2-acetoxyacrylonitrile) and its phenylene and alkylene bis homologs. Preparation, isomerization, and intramolecular [2 + 2] photocycloaddition
  作者：Akira Oku、Shinichi Urano、Toshiyuki Nakaji、Ge Qing、Manabu Abe

  DOI：10.1021/jo00034a015

  日期：1992.4

  The title compounds, 1,4-diacetoxy-1,4-dicyano-1,3-butadiene (3), 1,6-diacetoxy-1,6-dicyano-1,5-hexadiene (8), 1,2-bis(2-acetoxy-2-cyanovinyl)benzene (13), and 1,4-bis(2-acetoxy-2-cyanovinyl)benzene (17) were prepared by acetylation of the corresponding diacyl dicyanides. Dicyanides were prepared from diacyl chlorides by reaction with cyanotrimethylsilane or the NaI-Cu2(CN)2 reagent. Among the three geometrical isomers of the title compounds, the Z,Z diene predominated in 8 whereas E,E dienes predominated in conjugated dienes 3, 13, and 17. Conjugated E,E dienes underwent photoisomerization to E,Z and Z,Z isomers much faster than unconjugated diene 8. Prolonged irradiation on 13 yielded intramolecular [2 + 2] cycloadducts endo, exo- and exo,exo-5,6-diacetoxy-5,6-dicyano-2,3-benzobicyclo[2.1.1]hex-2-ene (22). Photochemistry in the formation of 22 is discussed.