4-(4-chlorophenyl)-4-azatricyclo[5.2.1.0^2,6endo]dec-8-ene-3,5-dione | 89104-84-7

• 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: 4-(4-chlorophenyl)-4-azatricyclo[5.2.1.0^2,6endo]dec-8-ene-3,5-dione
• 英文别名: (3aR,4S,7R,7aS)-2-(4-chlorophenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione；(1S,2R,6S,7R)-4-(4-chlorophenyl)-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• CAS: 89104-84-7
• 化学式: C₁₅H₁₂ClNO₂
• 分子量: 273.719
• InChiKey: HRUJXLSUPUNTBP-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：

  4-(4-chlorophenyl)-4-azatricyclo[5.2.1.0^2,6endo]dec-8-ene-3,5-dione 在 过氧乙酸 、 硫酸 、 水 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Spatial arrangement of norbornanedicarboxylic acids N-arylimides

  摘要：

  The effect of substituents on the spatial arrangement of norbornane compounds was investigated. Norbornanedicarboxylic acids N-arylimides with OCH(3), Cl, NO(2) groups in the ortho-position of the aromatic ring form as conformational isomers with hindered rotation. The specific spatial isomerism is confirmed by the quantum-chemical calculations.

  DOI：

  10.1134/s1070428010110023
• 作为产物：
  描述：

  对氯苯胺 、 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以86%的产率得到4-(4-chlorophenyl)-4-azatricyclo[5.2.1.0^2,6endo]dec-8-ene-3,5-dione
  参考文献：
  名称：

  烯烃复分解中的目标特定策略：顺式-顺式-顺式-三喹烷和-螺环烷的合成方法

  摘要：

  已经通过烯烃复分解反应（从外萘酸酐开始）证明了一种简单，简单的合成顺式-顺式-顺式-三喹烷和-丙炔的方法。该方法涉及使用Grubb's催化剂的降冰片烯衍生物的开环和闭环复分解序列。降冰片烯衍生物的早期二烯丙基化被证明，随后是闭环复分解，其仅递送螺旋桨。出人意料的是，开环复分解，后期的二烯丙基化反应以及随后的闭环复分解反应产生了三喹烷以及丙炔衍生物。

  DOI：

  10.1021/acs.orglett.6b00537

文献信息

• 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。
• 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。
• 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。
• Fused cyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function
  申请人：——

  公开号：US20040087548A1

  公开（公告）日：2004-05-06

  Fused cyclic compounds, methods of using such compounds in the treatment of nuclear hormone receptor-associated conditions such as cancer and immune disorders, and pharmaceutical compositions containing such compounds.

  融合的环状化合物，使用这种化合物治疗与核激素受体相关的疾病，如癌症和免疫紊乱的方法，以及包含这种化合物的制药组合物。
• Stereochemistry of dihydroxylation of N-arylbicyclo[2.2.1]-hept-5-ene-endo- and -exo-2,3-dicarboximides
  作者：B. T. Bagmanov

  DOI：10.1134/s1070428007110097

  日期：2007.11

  Stereochemistry of the oxidation of N-arylbicyclo[2.2.1]hept-5-ene-endo-and-exo-2,3-dicarboximides at the double bond with peroxyacetic acid generated in situ in the presence of sulfuric acid and with an anhydrous dioxane solution of peroxyacetic acid was studied. In both cases, the reaction was stereospecific, regardless of the substituent in the N-aryl group and configuration of the imide ring, but the reaction direction depended on the presence of water in the system. In the first case, the corresponding trans-5,6-dihydroxy derivatives were formed, while in the second, exo-5,6-epoxy derivatives. The oxidation of N-arylbicyclo[2.2.1]-hept-5-ene-endo-and-exo-2,3-dicarboximides with a solution of potassium permanganate in aqueous acetone gave the corresponding N-aryl-cis-5,6-dihydroxybicyclo[2.2.1]heptane-endo-and-exo-2,3-dicarboximides. The exo,cis,exo and exo,cis,endo configurations of the synthesized compounds were determined by H-1 NMR spectroscopy.