3-endo-(benzylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-endo-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: 3-endo-(benzylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid
• 英文别名: endo-3-(N-benzylcarbamoyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid；(1R,2S,3R,4S)-3-(benzylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: QCXUJIJIBRKJBL-RQJABVFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  3-endo-(benzylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid 在 甲酸 、 双氧水 作用下， 以 水 为溶剂， 反应 120.0h， 以75%的产率得到benzylammonium exo-2-hydroxy-5-oxo-4-oxatricyclo-[4.2.1.0^3,7]nonane-endo-9-carboxylate
  参考文献：
  名称：

  Lactonation of N-alkyl-and N,N-dialkylamido acids of norbornene series in reactions with performic acid

  摘要：

  Reaction products were obtained from bicyclo[2.2.1]hept-5-ene-endo,endo-2,3-dicarboxylic (endic) acid anhydride and ammonia, methyl-, benzyl-, dimethyl-, methylbenzyl-, dibenzyl-, diethyl-, dipropyl-, diisopropyl-, and dipentylamines. The synthesized amido acids were subjected to epoxidation by organic peracids. The structure of compounds obtained was confirmed by IR, H-1 and C-13 NMR spectra, and in some instances, by X-ray diffraction analysis.

  DOI：

  10.1134/s1070428007050053
• 作为产物：
  描述：

  3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 、 苯甲醇 以 苯 为溶剂， 反应 48.0h， 以90%的产率得到3-endo-(benzylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid
  参考文献：
  名称：

  Lactonation of N-alkyl-and N,N-dialkylamido acids of norbornene series in reactions with performic acid

  摘要：

  Reaction products were obtained from bicyclo[2.2.1]hept-5-ene-endo,endo-2,3-dicarboxylic (endic) acid anhydride and ammonia, methyl-, benzyl-, dimethyl-, methylbenzyl-, dibenzyl-, diethyl-, dipropyl-, diisopropyl-, and dipentylamines. The synthesized amido acids were subjected to epoxidation by organic peracids. The structure of compounds obtained was confirmed by IR, H-1 and C-13 NMR spectra, and in some instances, by X-ray diffraction analysis.

  DOI：

  10.1134/s1070428007050053

文献信息

• A synthesis of succinimides and glutarimides from cyclic anhydrides
  作者：Tadashi Kometani、Tony Fitz、David S. Watt

  DOI：10.1016/s0040-4039(00)84137-4

  日期：1986.1

  The transformation of cyclic anhydrides to their corresponding imides involves a mild three-step sequence: (1) reaction with a primary amine, (2) conversion of the intermediate monoamide to an N-hydroxysuccinimidyl ester using N,N′-disuccinimidyl oxalate (DSO), and (3) cyclization by heating the NHS ester in trichloroethylene in the presence of 4-(dimethylamino)pyridine.

  环状酸酐向其相应的酰亚胺的转化涉及温和的三个步骤：（1）与伯胺反应，（2）使用N，N'-二琥珀酰亚胺草酸酯（DSO）将中间体单酰胺转化为N-羟基琥珀酰亚胺酯），和（3）在4-氯代二甲基氨基吡啶存在下，在三氯乙烯中加热NHS酯来环化。
• Lactonization of epoxyendic anhydride in reactions with amines
  作者：L. I. Kas’yan、O. V. Krishchik、I. N. Tarabara、A. O. Kas’yan、V. A. Pal’chikov

  DOI：10.1134/s1070428006040051

  日期：2006.4

  Reactions of exo-5,6-epoxybicyclo[2.2.1]hept-5-ene-endo-2,endo-3-dicarboxylic anhydride (epoxyendic anhydride) with acyclic, aromatic, heteroaromatic, and nonaromatic heterocyclic amines afforded the corresponding heterocyclization products, substituted exo-2-hydroxy-5-oxo-4-oxatricyclo[4.2. 1.0(3,7)]nonaneendo-9-carboxamides (oxabrendanes), whose structure was confirmed by the IR and H-1 and C-13 NMR (including two-dimensional) spectra. Other approaches to the tricyclic compounds were also examined, in particular via reactions of organic peroxy acids with amido acids obtained by aminolysis of endic anhydride.
• Badri, Rashid; Heidarizadeh, Fariba, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 5, p. 1000 - 1003
  作者：Badri, Rashid、Heidarizadeh, Fariba

  DOI：——

  日期：——