3-(4-nitrophenyl)bicyclo[2.2.1]hepta-2,5-diene-2-carbaldehyde | 355392-18-6

• 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: 3-(4-nitrophenyl)bicyclo[2.2.1]hepta-2,5-diene-2-carbaldehyde
• CAS: 355392-18-6
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: TZEAMTDHANKQAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-nitrophenyl)bicyclo[2.2.1]hepta-2,5-diene-2-carbaldehyde 在 sodium hydroxide 、 锌 作用下， 以 水 、 异丙醇 为溶剂， 反应 0.5h， 以91%的产率得到4,4'-bis(3-formylbicyclo[2.2.1]hepta-2,5-dien-2-yl)azobenzene
  参考文献：
  名称：

  摘要：

  3-(4-Nitrophenyl)bicyclo[2.2.1]hepta-2,5-diene-2-carbaldehyde and its derivatives at the formyl group were synthesized. By reduction of the nitro group the corresponding 3-(4-aminophenyl)-substituted compounds were obtained, as well as 4,4'-bis(bicyclo[2.2.1]hepta-2,5-dien-2-yl)azobenzenes. Irradiation of the resulting norbornadiene derivatives in the region of their absorption maxima resulted in valence isomerization with Formation of the corresponding quadricyclanes. The reverse transformations are promoted by molybdenum(VI) oxide as heterogeneous catalyst. 4,4'-Bis(bicyclo[2.2.1]hepta-2,5-dien-2-yl)azobenzenes undergo reversible (on heating) photochemical E/Z isomerization at the N=N bond.

  DOI：

  10.1023/a:1012325417400
• 作为产物：
  描述：

  (4-硝基苯基)炔丙醛 、 环戊二烯 以 甲苯 为溶剂， 反应 4.0h， 以60%的产率得到3-(4-nitrophenyl)bicyclo[2.2.1]hepta-2,5-diene-2-carbaldehyde
  参考文献：
  名称：

  摘要：

  3-(4-Nitrophenyl)bicyclo[2.2.1]hepta-2,5-diene-2-carbaldehyde and its derivatives at the formyl group were synthesized. By reduction of the nitro group the corresponding 3-(4-aminophenyl)-substituted compounds were obtained, as well as 4,4'-bis(bicyclo[2.2.1]hepta-2,5-dien-2-yl)azobenzenes. Irradiation of the resulting norbornadiene derivatives in the region of their absorption maxima resulted in valence isomerization with Formation of the corresponding quadricyclanes. The reverse transformations are promoted by molybdenum(VI) oxide as heterogeneous catalyst. 4,4'-Bis(bicyclo[2.2.1]hepta-2,5-dien-2-yl)azobenzenes undergo reversible (on heating) photochemical E/Z isomerization at the N=N bond.

  DOI：

  10.1023/a:1012325417400

文献信息

• ——
  作者：A. D. Dubonosov、S. V. Galichev、V. A. Chernoivanov、V. A. Bren'、V. I. Minkin

  DOI：10.1023/a:1012325417400

  日期：——

  3-(4-Nitrophenyl)bicyclo[2.2.1]hepta-2,5-diene-2-carbaldehyde and its derivatives at the formyl group were synthesized. By reduction of the nitro group the corresponding 3-(4-aminophenyl)-substituted compounds were obtained, as well as 4,4'-bis(bicyclo[2.2.1]hepta-2,5-dien-2-yl)azobenzenes. Irradiation of the resulting norbornadiene derivatives in the region of their absorption maxima resulted in valence isomerization with Formation of the corresponding quadricyclanes. The reverse transformations are promoted by molybdenum(VI) oxide as heterogeneous catalyst. 4,4'-Bis(bicyclo[2.2.1]hepta-2,5-dien-2-yl)azobenzenes undergo reversible (on heating) photochemical E/Z isomerization at the N=N bond.