endo-3-(p-bromophenylcarbamoyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid

• 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: endo-3-(p-bromophenylcarbamoyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid
• 英文别名: (1R,2S,3R,4S)-3-[(4-bromophenyl)carbamoyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• 化学式: C₁₅H₁₄BrNO₃
• 分子量: 336.185
• InChiKey: QKTOOJLUGWYJOZ-DTVLGXAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  endo-3-(p-bromophenylcarbamoyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid 在 吗啉 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到2-(4-bromophenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3-dione
  参考文献：
  名称：

  Endic acid diamides. Synthesis and reactivity

  摘要：

  A number of symmetric and unsymmetric endo-cis-dicarboxamides of the norbornene series containing dimethyl- and diethylamine, morpholine, perhydroazepine, and p-bromoaniline fragments were synthesized starting from endic anhydride with the aid of N,N'-dicyclohexylcarbodiimide. Oxidation of these amides with organic peroxy acids according to Prilezhaev gave exo-2-hydroxy-5-oxo-4-oxatricyclo[4.2.1.0(3,7)]-nonane-endo-9-carboxylic acid salts. The structure of the obtained products was confirmed by IR and H-1 NMR spectroscopy.

  DOI：

  10.1134/s107042800707007x
• 作为产物：
  描述：

  4-溴苯胺 、 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 以 苯 为溶剂， 以98%的产率得到endo-3-(p-bromophenylcarbamoyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid
  参考文献：
  名称：

  Endic acid diamides. Synthesis and reactivity

  摘要：

  A number of symmetric and unsymmetric endo-cis-dicarboxamides of the norbornene series containing dimethyl- and diethylamine, morpholine, perhydroazepine, and p-bromoaniline fragments were synthesized starting from endic anhydride with the aid of N,N'-dicyclohexylcarbodiimide. Oxidation of these amides with organic peroxy acids according to Prilezhaev gave exo-2-hydroxy-5-oxo-4-oxatricyclo[4.2.1.0(3,7)]-nonane-endo-9-carboxylic acid salts. The structure of the obtained products was confirmed by IR and H-1 NMR spectroscopy.

  DOI：

  10.1134/s107042800707007x

文献信息

• Endic acid diamides. Synthesis and reactivity
  作者：V. A. Pal’chikov、I. N. Tarabara、L. I. Kas’yan

  DOI：10.1134/s107042800707007x

  日期：2007.7

  A number of symmetric and unsymmetric endo-cis-dicarboxamides of the norbornene series containing dimethyl- and diethylamine, morpholine, perhydroazepine, and p-bromoaniline fragments were synthesized starting from endic anhydride with the aid of N,N'-dicyclohexylcarbodiimide. Oxidation of these amides with organic peroxy acids according to Prilezhaev gave exo-2-hydroxy-5-oxo-4-oxatricyclo[4.2.1.0(3,7)]-nonane-endo-9-carboxylic acid salts. The structure of the obtained products was confirmed by IR and H-1 NMR spectroscopy.