N-(benzoylamino)bicyclo[2.2.1]hept-2-ene-endo,endo-5,6-dicarboximide | 40956-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(benzoylamino)bicyclo[2.2.1]hept-2-ene-endo,endo-5,6-dicarboximide
• 英文别名: [(3aRS,4SR,7RS,7aSR)-1,3,3a,4,7,7a-hexahydro-1,3-dioxo-4,7-methano-2H-isoindol-2-yl]benzamide；N-[(1R,2S,6R,7S)-3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl]benzamide
• CAS: 40956-06-7
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: CRCNCQLDJVXUIQ-MPZDIEGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(benzoylamino)bicyclo[2.2.1]hept-2-ene-endo,endo-5,6-dicarboximide 在 甲酸 、 水 、 双氧水 作用下， 以72%的产率得到N-(benzoylamino)-exo-2,3-epoxybicyclo[2.2.1]heptane-endo,endo-5,6-dicarboximide
  参考文献：
  名称：

  内酸酐与肼和酰基肼的反应

  摘要：

  Reaction products of bicyclo[2.2.1]hept-2-ene-endo, endo-5,6-dicarboxylic (endic) acid with hydrazines and acylhydrazines were prepared. The features distinguishing of these reactions from those with amines were revealed. The compounds obtained were characterized by H-1, C-11 NMR, and IR spectra. The assignment of the signals in NMR spectra was done with the use of quantum-chemical calculations of chemical shifts performed by the density functional method. The structure of one among compounds synthesized, N-(m-hydroxybenzoylamino)-bicyclo[2.2.1] hept-2-ene-endo, endo-5,6-dicarboxamide, was proved by X-ray diffraction analysis.

  DOI：

  10.1023/b:rujo.0000045895.04509.2d
• 作为产物：
  描述：

  苯甲酰肼 、 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 硫酸 作用下， 以 乙醇 为溶剂， 以96%的产率得到N-(benzoylamino)bicyclo[2.2.1]hept-2-ene-endo,endo-5,6-dicarboximide
  参考文献：
  名称：

  内酸酐与肼和酰基肼的反应

  摘要：

  Reaction products of bicyclo[2.2.1]hept-2-ene-endo, endo-5,6-dicarboxylic (endic) acid with hydrazines and acylhydrazines were prepared. The features distinguishing of these reactions from those with amines were revealed. The compounds obtained were characterized by H-1, C-11 NMR, and IR spectra. The assignment of the signals in NMR spectra was done with the use of quantum-chemical calculations of chemical shifts performed by the density functional method. The structure of one among compounds synthesized, N-(m-hydroxybenzoylamino)-bicyclo[2.2.1] hept-2-ene-endo, endo-5,6-dicarboxamide, was proved by X-ray diffraction analysis.

  DOI：

  10.1023/b:rujo.0000045895.04509.2d

文献信息

• An Investigation into Domino-Heck Reactions ofN-Acylamino-Substituted Tricyclic Imides: Synthesis of New Prospective Pharmaceuticals
  作者：Emine Bagdatli、Nüket Öcal、Dieter E. Kaufmann

  DOI：10.1002/hlca.200790244

  日期：2007.12

  Heck and domino-Heck reactions of unsaturated N-acylamino-substituted tricyclic imides with aryl(heteroaryl) iodides and phenyl- or (trimethylsilyl)acetylene were either carried out in the presence of formate or phenyl- and (trimethylsilyl)acetylene, respectively. The CC coupling reactions appeared to be completely diastereoselective, giving the corresponding N-acylamino-5-exo-aryl (heteroaryl)- (5a–c

  不饱和N-酰基氨基取代的三环酰亚胺与芳基（杂芳基）碘化物和苯基或（三甲基甲硅烷基）乙炔的Heck和Domino- Heck反应分别在甲酸酯或苯基和（三甲基甲硅烷基）乙炔的存在下进行。CC偶联反应似乎是完全非对映选择性的，得到相应的N-酰基氨基-5- exo-芳基（杂芳基）-（5a – c，6a，b），N-（苯甲酰基氨基）-5- exo-苯基-6- exo -[（三甲基甲硅烷基）乙炔基]-（5d）或5- exo-（4-氯苯基）-N-（2，2-二甲基丙酰基氨基）-6-外-（苯基乙炔基）双环[2.2.1]庚烷-2-内酯，3-内-二甲叉酰亚胺（6c）（方案3和4）。
• Reaction of Endic Anhydride with Hydrazines and Acylhydrazines
  作者：O. V. Krishchik、I. N. Tarabara、A. O. Kas'yan、S. V. Shishkina、O. V. Shishkin、A. K. Isaev、L.I. Kas'yan

  DOI：10.1023/b:rujo.0000045895.04509.2d

  日期：2004.8

  Reaction products of bicyclo[2.2.1]hept-2-ene-endo, endo-5,6-dicarboxylic (endic) acid with hydrazines and acylhydrazines were prepared. The features distinguishing of these reactions from those with amines were revealed. The compounds obtained were characterized by H-1, C-11 NMR, and IR spectra. The assignment of the signals in NMR spectra was done with the use of quantum-chemical calculations of chemical shifts performed by the density functional method. The structure of one among compounds synthesized, N-(m-hydroxybenzoylamino)-bicyclo[2.2.1] hept-2-ene-endo, endo-5,6-dicarboxamide, was proved by X-ray diffraction analysis.