4-benzylidene-1-cyclohexyl-2,3-dioxopyrrolidine | 4805-31-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-benzylidene-1-cyclohexyl-2,3-dioxopyrrolidine
• 英文别名: 2,3-Dioxo-1-cyclohexyl-4-benzyliden-pyrrolidin；4-Benzyliden-1-cyclohexyl-2,3-dioxo-pyrrolidin；4-benzylidene-1-cyclohexyl-pyrrolidine-2,3-dione；4-Benzylidene-1-cyclohexylpyrrolidine-2,3-dione
• CAS: 4805-31-6
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: BMVPXJGIEHAUIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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-benzylidene-1-cyclohexyl-2,3-dioxopyrrolidine 在 氧气 、 ammonium formate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 2,6-Dicyclohexyl-8-phenyl-1,2,6,7-tetrahydro-2,4,6-triaza-s-indacene-3,5-dione
  参考文献：
  名称：

  Snyder, Carroll A.; Thorn, Mark A.; Klijanowicz, James E., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 603 - 607

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Cyclohexyl-4-carboethoxy-2,3-dioxopyrrolidine 、 苯甲醛 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以73%的产率得到4-benzylidene-1-cyclohexyl-2,3-dioxopyrrolidine
  参考文献：
  名称：

  Syntheses and Reactions of 2-Cyclohexyl-1,3,4,5-tetrahydro-10H-pyrrolo[3,4-b][1,5]benzodiazepine-1,4-dione and 4-Aryl-2-cyclohexyl-1,3,4,10-tetrahydropyrrolo[4,3-c][1,5]benzothiazepin-1-ones

  摘要：

  2-Cyclohexyl-1,3,4,5-tetrahydro-10H-pyrrolo[3,4-b][1,5]benzodiazepine- 1,4-dione was synthesized by heating a solution of ethyl 1-cyclohexyl-2,3-dioxopyrrolidine-4-carboxylate and o-phenylenediamine in acetic acid. Alkylation and acylation of the synthesized compound were examined. 4-Aryl-2-cyclohexyl-1,3,4,10-tetrahydropyrrolo[4,3-c][1,5]benzothiazepin-1-ones were synthesized by Michael addition of 2-aminothiophenol to 4-arylidene-1-cyclohexyl-2,3-dioxopyrrolidines and concomitant dehydrative cyclization.

  DOI：

  10.3987/com-05-10514

文献信息

• Copper Catalyzed Diastereo- and Enantioselective 1,4-Addition Michael Reaction of 2,3-Dioxopyrrolidines with Nitroalkanes in Aqueous Media
  作者：Yekai Huang、Zhenggen Zha、Zhiyong Wang

  DOI：10.1021/acs.orglett.0c00030

  日期：2020.4.3

  A good diastereo- and enantioselective 1,4-addition Michael reaction catalyzed by a chiral copper complex was developed in aqueous media. A series of nitro-containing pyrrolidones could be gained in high yields with excellent diastereoselectivities and good ee values by virtue of this developed method. It affords a facile access to construct carbon-carbon bonds with water and air tolerance. Furthermore

  在水介质中开发了由手性铜配合物催化的良好的非对映和对映选择性的1,4-加成Michael反应。借助这种发达的方法，可以高收率获得一系列具有硝基的吡咯烷酮类化合物，它们具有出色的非对映选择性和良好的ee值。它提供了构建具有水和空气耐受性的碳-碳键的便捷途径。此外，成功地进行了克级合成，得到了相应的产物。
• Lewis acid catalyzed annulation of spirocyclic donor–acceptor cyclopropanes with <i>exo</i>-heterocyclic olefins: access to highly functionalized bis-spirocyclopentane oxindole frameworks
  作者：Kuldeep Singh、Sourav Pramanik、Trevor A. Hamlin、Biplab Mondal、Dinabandhu Das、Jaideep Saha

  DOI：10.1039/c9cc03393a

  日期：——

  Lewis acid catalyzed highly efficient [3+2] annulation of spirocyclic Donor–Acceptor cyclopropanes (DACs) with exo-heterocyclic olefins is reported to furnish various biologically relevant dispiro-2,3-dioxopyrrolidine[cyclopentane]oxindole and dispiropyrazolone[cyclopentane]oxindole frameworks. This report highlights the use of oxindole-activated spiro-DACs as potential synthons to access complex dispirocarbocyclic

  据报道，路易斯酸催化的螺环供体-受体环丙烷（DACs）与环外杂环烯烃的高效[3 + 2]环合提供了各种生物学上相关的二螺-2,3-二氧杂吡咯烷[环戊烷] ox吲哚和二螺并吡唑啉酮[环戊烷] ox吲哚骨架。该报告重点介绍了使用羟吲哚活化的螺-DAC作为潜在的合成子，通过前者的扩环来获得复杂的双螺碳环羟吲哚，具有高收率和非对映选择性。
• Efficient enantioselective synthesis of trisubstituted γ-lactam <i>via</i> the Michael addition reaction of 2,3-dioxopyrrolidine with indole in aqueous media
  作者：John Kamanda Mansaray、Yekai Huang、Kuiliang Li、Xiang Sun、Zhenggen Zha、Zhiyong Wang

  DOI：10.1039/d2ob00959e

  日期：——

  An efficient enantioselective Michael addition reaction of 2,3-dioxopyrrolidine with indole in aqueous media was developed by virtue of a chiral copper complex. This reaction features air tolerance, a broad substrate scope and mild reaction conditions. Furthermore, a gram-scale synthesis was conducted to afford the corresponding products with a high yield and excellent enantioselectivity. Moreover

  借助手性铜络合物，开发了 2,3-二氧代吡咯烷与吲哚在水性介质中的高效对映选择性迈克尔加成反应。该反应具有耐空气性、底物范围广、反应条件温和等特点。此外，还进行了克级合成以提供具有高产率和优异对映选择性的相应产物。此外，所提出的机制得到了控制实验、XPS 研究和 DFT 计算的支持。