endo-N-4-trifluoromethylphenyl-norbornene-5,6-dicarboximide | 1026999-29-0

• 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: endo-N-4-trifluoromethylphenyl-norbornene-5,6-dicarboximide
• 英文别名: endo-4-(4-trifluoromethylphenyl)-4-aza-tricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione；(1S,2R,6S,7R)-4-[4-(trifluoromethyl)phenyl]-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• CAS: 1026999-29-0
• 化学式: C₁₆H₁₂F₃NO₂
• 分子量: 307.272
• InChiKey: BSEVBIJSEUMTNE-KGOITJQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  endo-N-4-trifluoromethylphenyl-norbornene-5,6-dicarboximide 、 丙酮氰醇 在 (R)-(+)-5,5'-双[二(3,5-二甲苯基)膦]-4,4'-二-1,3-苯并二茂 、 bis(1,5-cyclooctadiene)nickel (0) 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以96%的产率得到
  参考文献：
  名称：

  降冰片烯衍生物的对映选择性镍催化氢氰酸去对称化

  摘要：

  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。

  DOI：

  10.1021/acscatal.1c01971
• 作为产物：
  描述：

  1-(4-(三氟甲基)苯基)-1H-吡咯-2,5-二酮 、 环戊二烯 反应 0.5h， 以95%的产率得到endo-N-4-trifluoromethylphenyl-norbornene-5,6-dicarboximide
  参考文献：
  名称：

  Mechanochemical Diels-Alder Cycloaddition Reactions for Straightforward Synthesis of endo-Norbornene Derivatives

  摘要：

  在机械化学研磨条件下，环戊二烯与顺丁烯二酸酐和马来酰亚胺衍生物的 Diels-Alder 环加成反应进行得非常顺利，只产生了内降冰片烯，而且产量很高。所有转化过程均在室温下完成，无需使用任何催化剂或有机溶剂，因此操作和纯化过程非常简单。此外，还对传统条件和其他暂定条件进行了对照实验。

  DOI：

  10.1055/s-0030-1259030

文献信息

• The effect of fluorine atoms on gas transport properties of new polynorbornene dicarboximides
  作者：Joel Vargas、Araceli Martínez、Arlette A. Santiago、Mikhail A. Tlenkopatchev、Rubén Gaviño、Manuel Aguilar-Vega

  DOI：10.1016/j.jfluchem.2008.09.011

  日期：2009.2

  The new N-4-trifluoromethylphenyl-norbornene-5,6-dicarboximide (2a) and N-3,5-bis(trifluoromethyl)phenyl-norbornene-5,6-dicarboximide (2b) mixtures of exo and endo monomers were synthesized and polymerized via ring opening metathesis polymerization (ROMP) using bis(tricyclohexylphosphine) benzylidene ruthenium(IV) dichloride (I) and tricyclohexylphosphine 11,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene] ruthenium dichloride (II) to produce the corresponding polynorbornene dicarboximides Poly-2a and Poly-2b, respectively. The transport of five gases He. N-2, O-2, CO2 and CH4 across membranes prepared from Poly-2a was determined at 35 degrees C using a constant volume permeation cell. The gas transport properties of the fluorine containing polymer Poly2a were compared with those found for membranes from non-fluorinated poly(N-phenyl-exo-elidonorbornene-5,6-dicarboximide) (P-PhNDI). Gas permeability, diffusion and solubility coefficients of the fluorine containing polynorbornene Poly-2a were up to an order of magnitude larger than those of the non-fluorinated one. Poly-2a was found to have one of the largest gas transport coefficients reported to date in glassy polynorbornene dicarboximides. (C) 2008 Elsevier B.V. All rights reserved.
• 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 Diels-Alder Cycloaddition Reactions for Straightforward Synthesis of endo-Norbornene Derivatives
  作者：Ze Zhang、Zhi-Wei Peng、Ming-Feng Hao、Jian-Gang Gao

  DOI：10.1055/s-0030-1259030

  日期：2010.12

  Under mechanochemical milling conditions, Diels-­Alder cycloaddition of cyclopentadiene with maleic anhydride and maleimide derivatives proceeded very smoothly, affording endo-norbornenes exclusively in quantitative yield. All the transformations were accomplished at room temperature without using any catalyst or organic solvent, thus the workup and purification procedure is very simple. Control experiments on traditional and other tentative conditions were also investigated.

  在机械化学研磨条件下，环戊二烯与顺丁烯二酸酐和马来酰亚胺衍生物的 Diels-Alder 环加成反应进行得非常顺利，只产生了内降冰片烯，而且产量很高。所有转化过程均在室温下完成，无需使用任何催化剂或有机溶剂，因此操作和纯化过程非常简单。此外，还对传统条件和其他暂定条件进行了对照实验。