N-(p-iodophenyl)bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboximide | 521301-37-1

• 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-(p-iodophenyl)bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboximide
• 英文别名: (1S,2R,6S,7R)-4-(4-iodophenyl)-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• CAS: 521301-37-1
• 化学式: C₁₅H₁₂INO₂
• 分子量: 365.17
• InChiKey: QABUSKAILYZTBL-KGOITJQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 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-(p-iodophenyl)bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboximide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以68.3%的产率得到N-phenyl-4-azatricyclo[5.2.1.0^2,6]dec-8-ene
  参考文献：
  名称：

  摘要：

  4-Azatricyclo[5.2.1.0(2,6)]dec-8-ene and its N-phenyl derivative were synthesized by reaction of endic anhydride with amines, transformation of the amido acids thus obtained to imides, and subsequent reduction of the latter with lithium aluminum hydride. The unsubstituted tricyclic amine was brought into reactions with electrophilic reagents: p-toluenesulfonyl chloride, p-toluoyl chloride, m-tolyl isocyanate, phenyl isothiocyanate, and endic anhydride to obtain a number of new derivatives; also, the corresponding salt with 1-adamantanecarboxylic acid was isolated. N-(p-Tolylsulfonyl)- and N-(m-tolylcarbamoyl)-4-azatricyclo-[5.2.1.0(2,6) ]dec-8-enes were oxidized to the corresponding 8,9-epoxy derivatives with monoperoxyphthalic acid. The structure of the products was confirmed by the data of IR, H-1 and C-13 NMR, and mass spectra. The molecular structures of N-(p-iodophenyl)bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboximide and N-phenyl-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene were established by X-ray analysis.

  DOI：

  10.1023/a:1021651712792
• 作为产物：
  描述：

  3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 以 溶剂黄146 、 苯 为溶剂， 反应 6.0h， 生成 N-(p-iodophenyl)bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboximide
  参考文献：
  名称：

  摘要：

  4-Azatricyclo[5.2.1.0(2,6)]dec-8-ene and its N-phenyl derivative were synthesized by reaction of endic anhydride with amines, transformation of the amido acids thus obtained to imides, and subsequent reduction of the latter with lithium aluminum hydride. The unsubstituted tricyclic amine was brought into reactions with electrophilic reagents: p-toluenesulfonyl chloride, p-toluoyl chloride, m-tolyl isocyanate, phenyl isothiocyanate, and endic anhydride to obtain a number of new derivatives; also, the corresponding salt with 1-adamantanecarboxylic acid was isolated. N-(p-Tolylsulfonyl)- and N-(m-tolylcarbamoyl)-4-azatricyclo-[5.2.1.0(2,6) ]dec-8-enes were oxidized to the corresponding 8,9-epoxy derivatives with monoperoxyphthalic acid. The structure of the products was confirmed by the data of IR, H-1 and C-13 NMR, and mass spectra. The molecular structures of N-(p-iodophenyl)bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboximide and N-phenyl-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene were established by X-ray analysis.

  DOI：

  10.1023/a:1021651712792

文献信息

• Catalytic Diastereospecific and Enantioselective (3 + 2) Transannulations of 1,2,3-Thiadiazoles with Strained Norbornene Derivatives
  作者：Cunzhi Chen、Shuyan Fang、Ziyang Dong、Jiaxi Xu、Zhanhui Yang

  DOI：10.1021/acs.orglett.2c00330

  日期：2022.3.25

  ring-strain-release strategy, iridium-catalyzed transannulations with norbornene derivatives are achieved in a diastereospecific and enantioselective manner. The first asymmetric transannulations of 1,2,3-thiadiazoles are reported.

  通过采用环应变释放策略，以非对映体和对映体选择性的方式实现了铱催化的降冰片烯衍生物的环化。报道了 1,2,3-噻二唑的第一个不对称环环化。
• Generation of Cyclopentadiene for <i>Diels–Alder</i> Reactions by Visible‐Light Irradiation of Iron Sandwich Complexes
  作者：Alexey S. Sokolov、Alexander V. Polezhaev、Yulia V. Nelyubina、Dmitry S. Perekalin

  DOI：10.1002/hlca.202100246

  日期：2022.4

  Cyclopentadienes readily undergo fast and selective Diels–Alder reactions which can be used for conjugation of biomolecules and polymers. Herein we present a new method for the photochemical generation of cyclopentadienes by the visible light irradiation of the iron complexes [(C5H4R)Fe(arene)]+. This reaction proceeds at room temperature, in water, and in the presence of potentially interfering amino

  环戊二烯很容易发生快速和选择性的 Diels-Alder反应，可用于生物分子和聚合物的缀合。在此，我们提出了一种通过铁络合物[(C 5 H 4 R)Fe(芳烃)] +的可见光照射光化学生成环戊二烯的新方法。该反应在室温、水中和存在潜在干扰氨基酸的情况下进行。游离的环戊二烯被亲双烯体捕获，得到相应的Diels-Alder加合物，产率为 72-95%。
• ——
  作者：I. N. Tarabara、A. O. Kas'yan、O. V. Krishchik、S. V. Shishkina、O. V. Shishkin、L. I. Kas'yan

  DOI：10.1023/a:1021651712792

  日期：——

  4-Azatricyclo[5.2.1.0(2,6)]dec-8-ene and its N-phenyl derivative were synthesized by reaction of endic anhydride with amines, transformation of the amido acids thus obtained to imides, and subsequent reduction of the latter with lithium aluminum hydride. The unsubstituted tricyclic amine was brought into reactions with electrophilic reagents: p-toluenesulfonyl chloride, p-toluoyl chloride, m-tolyl isocyanate, phenyl isothiocyanate, and endic anhydride to obtain a number of new derivatives; also, the corresponding salt with 1-adamantanecarboxylic acid was isolated. N-(p-Tolylsulfonyl)- and N-(m-tolylcarbamoyl)-4-azatricyclo-[5.2.1.0(2,6) ]dec-8-enes were oxidized to the corresponding 8,9-epoxy derivatives with monoperoxyphthalic acid. The structure of the products was confirmed by the data of IR, H-1 and C-13 NMR, and mass spectra. The molecular structures of N-(p-iodophenyl)bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboximide and N-phenyl-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene were established by X-ray analysis.