N-phenylbicyclo[2.2.1]hept-5-ene-2-endo,3-endo-dicarboximide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-phenylbicyclo[2.2.1]hept-5-ene-2-endo,3-endo-dicarboximide
• 英文别名: (3aR,4S,7R,7aS)-2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione；(1R,2S,6R,7S)-4-phenyl-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: GAONUEUNHBLHPP-NIFPGPBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-phenylbicyclo[2.2.1]hept-5-ene-2-endo,3-endo-dicarboximide 在 过氧乙酸 、 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 2-exo-hydroxy-5-oxo-4-oxatricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid
  参考文献：
  名称：

  摘要：

  Epoxidation of endo- and evo-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid N-arylimides with a solution of peracetic acid in anhydrous dioxane affords 5,6-exo-epoxybicycloheptanedicarboxylic acid N-arylimides. The epoxidation reaction is not sensitive to the configuration of the imide fragment, to the character and position of the substituent in the aromatic ring. The reaction is determined only by oxidation conditions.

  DOI：

  10.1023/a:1015573902465
• 作为产物：
  描述：

  3-endo-(N-phenylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid 以 溶剂黄146 为溶剂， 反应 6.0h， 生成 N-phenylbicyclo[2.2.1]hept-5-ene-2-endo,3-endo-dicarboximide
  参考文献：
  名称：

  Unusual reaction of endic anhydride with 2-methyl-2-phenylaminopropanenitrile

  摘要：

  DOI：

  10.1134/s107042800604021x

文献信息

• Synthesis of Diels–Alder adducts of N-arylmaleimides by a multicomponent reaction between maleic anhydride, dienes, and anilines
  作者：J. Alberto Guevara-Salazar、Delia Quintana-Zavala、Hugo A. Jiménez-Vázquez、José Trujillo-Ferrara

  DOI：10.1007/s00706-011-0515-5

  日期：2011.8

  AbstractWe have carried out the synthesis and characterization of some hexahydroisoindolyl benzoic acids and their corresponding ethyl esters by a multicomponent reaction (MCR) between aminobenzoic acids or aminobenzoates, maleic anhydride, and isoprene in the absence of catalysts. According to additional experiments, the MCR takes place by sequential formation of N-arylmaleamic acids from the aminobenzoic

  摘要我们在不存在催化剂的情况下，通过氨基苯甲酸或氨基苯甲酸酯，马来酸酐和异戊二烯之间的多组分反应（MCR），对一些六氢异吲哚基苯甲酸及其相应的乙酯进行了合成和表征。根据其他实验，MCR是通过依次从氨基苯甲酸或氨基苯甲酸酯和顺丁烯二酸酐，酸和异戊二烯的Diels–Alder加合物，最后是酰亚胺形成N-芳基马来酰胺酸而发生的。加合物的1 H NMR数据（耦合常数）表明，相应的环己烯环的优选构型是顺式-船，由密度泛函理论（DFT）构象分析和相应构象异构体自旋-自旋耦合常数的DFT计算所支持的事实。我们的MCR合成方法在其他加合物的合成中成功进行了测试，其中使用了环戊二烯和其他苯胺。 图形概要
• Synthesis and Characterization of Exo‐endo and Endo‐endo Benzenesulfonylaziridines
  作者：Evilazio da Silva Andrade、Ricardo José Nunes、Marina Uieara

  DOI：10.1081/scc-200028524

  日期：2004.1

  Abstract In the search for structural cyclic imide analogues of therapeutic interest, the synthesis, separation, and characterization of exo‐endo 3 and endo‐endo 4 stereoisomers of benzenesulfonylaziridines, not found in the literature, are described in this study. The benzenesulfonylaziridines were synthesized through a 1,3‐dipolar‐type reaction of p‐toluenesulfonylazide and different norbornenesuccinimides

  摘要 在寻找具有治疗意义的结构环状酰亚胺类似物的过程中，本研究描述了文献中未发现的苯磺酰氮丙啶外型 3 和内型 4 立体异构体的合成、分离和表征。苯磺酰氮丙啶是通过对甲苯磺酰叠氮和不同降冰片烯琥珀酰亚胺的 1,3-偶极型反应合成的。
• Unexpected <i>ortho</i>-Heck Reaction under the Catellani Conditions
  作者：Alexander J. Rago、Guangbin Dong

  DOI：10.1021/acs.orglett.0c00952

  日期：2020.5.15

  An unexpected ortho-Heck reaction has been discovered during the study of palladium/norbornene (Pd/NBE) catalysis. Under the Catellani reaction conditions in the presence of lithium salts and olefins, Heck coupling takes place at the ortho position instead of the commonly observed ipso position; meanwhile, a norbornyl group is introduced at the arene ipso position. Systematic deuterium labeling and

  在研究钯/降冰片烯（Pd / NBE）催化过程中发现了意外的Ortho-Heck反应。在Catellani反应条件下，在锂盐和烯烃的存在下，Heck偶联发生在邻位而不是通常观察到的ipso位置。同时，在芳烃的ipso位置引入了降冰片基。系统的氘标记和交叉实验表明不寻常的1,4-钯迁移/分子内氢转移途径。在这项研究中获得的知识可以为Pd / NBE催化的未来发展提供见识。
• Enantioselective Nickel-Catalyzed Hydrocyanative Desymmetrization of Norbornene Derivatives
  作者：Feilong Sun、Ting Wang、Gui-Juan Cheng、Xianjie Fang

  DOI：10.1021/acscatal.1c01971

  日期：2021.6.18

  nickel-catalyzed enantioselective hydrocyanation of N-aryl 5-norbornene-endocis-2,3-dicarboximides was reported. This desymmetrization process allows for a quick construction of both continuous stereogenic carbon centers and remote N–CAr atropisomeric chirality. Mechanism studies indicated that the resident carbonyl group of the substrates plays a key role in the enantioselectivity.

  报道了镍催化的N-芳基 5-降冰片烯-endocis-2,3-二甲酰亚胺的对映选择性氢氰化。这种去对称化过程允许快速构建连续的立体碳中心和远程 N-C Ar阻转异构手性。机理研究表明，底物的驻留羰基在对映选择性中起关键作用。
• Mechanochemical Grinding Diels–Alder Reaction: Highly Efficient and Rapid Access to Bi-, Tri-, and Tetracyclic Systems
  作者：Rama Peddinti、Jyoti Agarwal、Rashmi Rani

  DOI：10.1055/s-0036-1558970

  日期：2017.7

  Grinding of various electron-deficient dienophiles with diverse dienes in a pestle and mortar for 1–15 minutes afforded the corresponding Diels–Alder adducts in quantitative yields under catalyst-free and solvent-free conditions, without the necessity for any purification steps.

  在无催化剂和无溶剂的条件下，在研杵和研钵中用不同的二烯研磨各种缺电子的亲二烯体 1-15 分钟，得到相应的 Diels-Alder 加合物，在无催化剂和无溶剂的条件下，无需任何纯化步骤。