2,7-Dioxo-octandinitril | 80317-75-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,7-Dioxo-octandinitril
• 英文别名: 2,7-Dioxo-octandisaeure-1,8-dinitril (Adipoyldicyanid)；Hexanedioyl cyanide；hexanedioyl dicyanide
• CAS: 80317-75-5
• 化学式: C₈H₈N₂O₂
• 分子量: 164.164
• InChiKey: GMWJWHSWXXYTTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,7-Dioxo-octandinitril 在 硫化氢 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成 2,7-Dioxo-korksaeure-dithionamid
  参考文献：
  名称：

  Asinger,F. et al., Justus Liebigs Annalen der Chemie, 1966, vol. 691, p. 92 - 108

  摘要：

  DOI：
• 作为产物：
  描述：

  copper(I) cyanide 、 己二酰氯 在 phosphorus pentoxide 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 96.0h， 生成 2,7-Dioxo-octandinitril
  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

• Haase,K.; Hoffmann,H.M., Angewandte Chemie, 1982, vol. 94, p. 80
  作者：Haase,K.、Hoffmann,H.M.

  DOI：——

  日期：——
• HAASE, K.;HOFFMANN, H. M. R., ANGEW. CHEM., 1982, 94, N 1, 80
  作者：HAASE, K.、HOFFMANN, H. M. R.

  DOI：——

  日期：——
• Asinger,F. et al., Justus Liebigs Annalen der Chemie, 1966, vol. 691, p. 92 - 108
  作者：Asinger,F. et al.

  DOI：——

  日期：——
• 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.