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

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: endo-3-(morpholinocarbonyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid
• 英文别名: (1R,2S,3R,4S)-3-(morpholine-4-carbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: WLYUHCLZBSNNLJ-YTWAJWBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  endo-3-(morpholinocarbonyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid 在 甲酸 、 双氧水 作用下， 以 水 为溶剂， 以80%的产率得到morpholinium exo-2-hydroxy-5-oxo-4-oxatricyclo[4.2.1.0^3,7]nonane-endo-9-carboxylate
  参考文献：
  名称：

  Products of endic anhydride reaction with cyclic amines and their heterocyclization

  摘要：

  Products of reaction between bicyclo[2.2.1]hept-5-ene-eizdo-endo-2,3-dicarboxylic anhydride (endic anhydride) and cyclic amines were obtained. By an example of one of amido acids a conformational analysis was performed and character of hydro-en bonds was studied using quantum-chemical calculations by PM3 procedure. eiido-3-(4-Antipyrylcarbomoyl)-bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid with a secondary arnide group was converted into the corresponding carboximide which was epoxidized by performic acid.

  DOI：

  10.1134/s107042800611008x
• 作为产物：
  描述：

  吗啉 、 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 以 苯 为溶剂， 反应 24.0h， 以93%的产率得到endo-3-(morpholinocarbonyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid
  参考文献：
  名称：

  Products of endic anhydride reaction with cyclic amines and their heterocyclization

  摘要：

  Products of reaction between bicyclo[2.2.1]hept-5-ene-eizdo-endo-2,3-dicarboxylic anhydride (endic anhydride) and cyclic amines were obtained. By an example of one of amido acids a conformational analysis was performed and character of hydro-en bonds was studied using quantum-chemical calculations by PM3 procedure. eiido-3-(4-Antipyrylcarbomoyl)-bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid with a secondary arnide group was converted into the corresponding carboximide which was epoxidized by performic acid.

  DOI：

  10.1134/s107042800611008x

文献信息

• Amido acids of norbornene series in reactions with sulfonyl azides
  作者：I. V. Tkachenko、I. N. Tarabara、S. V. Shishkina、O. V. Shishkin、L. I. Kas’yan

  DOI：10.1134/s1070428009080053

  日期：2009.8

  In reaction of amido acids from the norbornene series with arenesunfonyl azides alongside the expected N, N-dialkyl-5-oxo-exo-2-aryisulfonylamino-4-oxatricyclo[4.2.1.0(3,7)]nonane-endo-9-carboxamides (oxabrendanones) the formation of zwitter-ions with a structure of 5-(N,N-dialkyliminio)-exo-2-arylsulfonylamino-4-oxatricyclo[4.2.1.0(3,7)]nonane-endo-9-carboxylates came as a Surprise. The structure of compounds obtained was confirmed by the analysis of their IR and H-1 NMR spectra. The molecular structure of one among the zwitter-ions was established by XRD analysis.
• 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.