(2E,4E)-2-(N-methyl-4-bromoanilino)-5-(2-methoxyphenyl)-2,4-pentadienenitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2E,4E)-2-(N-methyl-4-bromoanilino)-5-(2-methoxyphenyl)-2,4-pentadienenitrile
• 英文别名: (2E,4E)-2-(4-bromo-N-methylanilino)-5-(2-methoxyphenyl)penta-2,4-dienenitrile
• 化学式: C₁₉H₁₇BrN₂O
• 分子量: 369.261
• InChiKey: DCAZPMSRGKBEJY-FFEFAENFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(甲基(苯基)氨基)乙腈 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 生成 (2E,4E)-2-(N-methyl-4-bromoanilino)-5-(2-methoxyphenyl)-2,4-pentadienenitrile
  参考文献：
  名称：

  Solution and Solid-State Photochemistry of 2-Anilino-5-phenyl-2,4-pentadienenitriles

  摘要：

  2-(N-Methylanilino)-5-phenyl-2,4-pentadienenitrile (3) undergoes either isomerization or oxidative cleavage at the 2,3-double bond upon irradiation in solution, whereas it dimerizes in a regiospecific manner to give the [2 + 2] cycloaddition product 12 upon irradiation in the solid state. From the fluorescence spectra and semiempirical calculation, the excited state of 3 is proposed to be a twist intramolecular charge transfer species. The X-ray analysis indicates that molecules 3b orient appropriately with a reasonable distance for the [2 + 2] cycloaddition in the solid state. The distance between C2 and C3' is 525 pm, the longest distance known in solid-state [2 + 2] cycloadditions. 2-(N-Methyl-p-bromoanilino)-5-phenyl-2,4-pentadienenitrile (4) shows behavior similar to that of 3 in the solution and solid-state photochemistry, whereas analogs 7-10 having nitro substituents on the 5-phenyl rings do not dimerize upon irradiation in the solid state. Semiempirical calculation of the electronic structures is used to interprete the discrepancy of reactivity.

  DOI：

  10.1021/jo00098a037

文献信息

• Solution and Solid-State Photochemistry of 2-Anilino-5-phenyl-2,4-pentadienenitriles
  作者：Yah-Long Liang、Jim-Min Fang、Tahsin Chow、Tong-Ing Ho、Chi-Rung Lee、Yu Wang

  DOI：10.1021/jo00098a037

  日期：1994.9

  2-(N-Methylanilino)-5-phenyl-2,4-pentadienenitrile (3) undergoes either isomerization or oxidative cleavage at the 2,3-double bond upon irradiation in solution, whereas it dimerizes in a regiospecific manner to give the [2 + 2] cycloaddition product 12 upon irradiation in the solid state. From the fluorescence spectra and semiempirical calculation, the excited state of 3 is proposed to be a twist intramolecular charge transfer species. The X-ray analysis indicates that molecules 3b orient appropriately with a reasonable distance for the [2 + 2] cycloaddition in the solid state. The distance between C2 and C3' is 525 pm, the longest distance known in solid-state [2 + 2] cycloadditions. 2-(N-Methyl-p-bromoanilino)-5-phenyl-2,4-pentadienenitrile (4) shows behavior similar to that of 3 in the solution and solid-state photochemistry, whereas analogs 7-10 having nitro substituents on the 5-phenyl rings do not dimerize upon irradiation in the solid state. Semiempirical calculation of the electronic structures is used to interprete the discrepancy of reactivity.