1-(4-Ethylphenyl)-3-methylidenepyrrolidine-2,5-dione

• 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: 1-(4-Ethylphenyl)-3-methylidenepyrrolidine-2,5-dione
• 英文别名: 1-(4-ethylphenyl)-3-methylidenepyrrolidine-2,5-dione
• 化学式: C₁₃H₁₃NO₂
• mdl: MFCD28384440
• 分子量: 215.252
• InChiKey: SHAQQXOCYVFACL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  1-(4-Ethylphenyl)-3-methylidenepyrrolidine-2,5-dione 、 3-氨基-5,5-二甲基-2-环己烯-1-酮 在 溶剂黄146 作用下， 以52%的产率得到2-(7,7-dimethyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolin-3-yl)-N-(4-ethylphenyl)acetamide
  参考文献：
  名称：

  N-芳基衣康酰亚胺的级联再循环作为合成多官能八氢喹啉的新方法

  摘要：

  开发了Hantzsch反应的新变体，用于在与3-氨基环己基-2-烯酮反应的N-芳基itaconimides的区域选择性级联环化的基础上合成1,2,3,4,5,6,7,8-八氢喹啉。该多米诺过程的机理包括将烯胺酮进行亲核加成到衣康酰亚胺的活化的多键上，并进行分子内转酰胺基化，同时使中间体再循环。

  DOI：

  10.1007/s10593-019-02530-5

文献信息

• An efficient synthesis of new polyfunctional hexahydro pyrido[1,2-a]pyrazin-1-ones
  作者：Yana Yu. Shmoylova、Yuri A. Kovygin、Irina V. Ledenyova、Mikhail A. Prezent、Elena D. Daeva、Sergey V. Baranin、Khidmet S. Shikhaliev

  DOI：10.1016/j.mencom.2021.03.039

  日期：2021.3

  New polyfunctional hydrogenated pyrido[1,2-a]pyrazin- 1-ones were obtained by regioselective recyclization of N-arylitaconimides with alkyl (3-oxopiperazin-2-ylidene)acetates. The supposed cascade reaction pathway involves the Michael addition of the nucleophile to an activated double bond and subsequent intramolecular transamidation of the intermediate with simultaneous recycling.

  通过用烷基（3-氧代哌嗪-2-亚烷基）乙酸酯对N-芳基衣康酰亚胺的区域选择性再循环，获得了新的多官能氢化吡啶并[1,2 - a ]吡嗪-1-酮。所谓的级联反应途径涉及亲核试剂的迈克尔加成至活化的双键，以及随后的中间体的分子内氨基转移，同时进行再循环。
• Phosphine-catalyzed [3 + 2] annulation reaction: highly regio- and diastereoselective synthesis of 2-azaspiro[4.4]nonene-1,3-diones
  作者：Wenjun Luo、Haiwen Hu、Sanfei Nian、Liang Qi、Fei Ling、Weihui Zhong

  DOI：10.1039/c7ob01957b

  日期：——

  A novel phosphine-catalyzed [3+2] annulation of γ‑substituted allenoates with succinimides was developed, which was successfully applied to the synthesis of 2-azaspiro[4.4]nonenes-1,3-dione derivatives. The reaction afforded the desired products in moderate to high yields (up to 96%) with excellent regioselectivities and diastereoselectivities (up to >99 : 1 dr). A plausible reaction mechanism has

  开发了一种新型的膦催化的琥珀酰亚胺与γ-取代的烯酸酯的[3 + 2]环化反应，将其成功地用于2-氮杂螺[4.4]壬烯-1,3-二酮衍生物的合成。该反应以中等至高产率（高达96％）提供了所需的产物，具有优异的区域选择性和非对映选择性（高达＞ 99∶1dr）。基于先前的文献，也已经提出了合理的反应机理。
• A novel synthetic approach to hydroimidazo[1,5-<i>b</i>]pyridazines by the recyclization of itaconimides and HPLC–HRMS monitoring of the reaction pathway
  作者：Dmitry Yu Vandyshev、Khidmet S Shikhaliev、Andrey Yu Potapov、Michael Yu Krysin、Fedor I Zubkov、Lyudmila V Sapronova

  DOI：10.3762/bjoc.13.252

  日期：——

  The novel cascade two-stage reaction between itaconimides and 1,2-diamino-4-phenylimidazole proceeds regio- and chemoselectively to form tetrahydroimidazo[1,5-b]pyridazines and includes nucleophilic C-addition by the activated C=C double bond and subsequent intramolecular recyclization of the intermediate with the amino group involved.

  在咪唑酰亚胺和1,2-二氨基-4-苯基咪唑之间进行的新型级联双级反应以区域和化学选择性形成四氢咪唑并[1,5-b]吡嗪，并包括通过活性C=C双键的亲核C-加成和随后的中间体内分子回收化，其中氨基参与其中。
• A novel method for the synthesis of pyrimido[1,2-a]benzimidazoles
  作者：Dmitriy Yu. Vandyshev、Khidmet S. Shikhaliev、Anna V. Kokonova、Andrei Yu. Potapov、Maria G. Kolpakova、Artem L. Sabynin、Fedor I. Zubkov

  DOI：10.1007/s10593-016-1914-7

  日期：2016.7

  Condensation of 1,2-diaminobenzimidazole with N-arylitaconimides was studied. It was found that 2-(10-amino-N-aryl-2-oxo-2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazol-3-yl)acetamides were formed in the course of this reaction upon brief heating to reflux of the reagent mixture in 2-propanol in the presence of catalytic amounts of acetic acid.

  研究了1,2-二氨基苯并咪唑与N-芳基衣康酰亚胺的缩合反应。发现在该反应过程中形成了2-（10-氨基-N-芳基-2-氧代-2,3,4,10-四氢嘧啶基[1,2 - a ]苯并咪唑-3-基）乙酰胺。在催化量的乙酸存在下，短暂加热反应混合物在2-丙醇中的回流。
• Recyclization of N-arylitaconimides with carboximidamides – a novel efficient method for the synthesis of 2-(2-amino-6-oxo- 1,4,5,6-tetrahydropyrimidin-5-yl)acetanilides
  作者：Nikita M. Sotnikov、Yurii А. Kovygin、Dmitrii Yu. Vandyshev、Irina V. Ledenyova、Yevgeniya А. Kosheleva、Oleg А. Kozadyorov、Khidmet S. Shikhaliev

  DOI：10.1007/s10593-021-02887-6

  日期：2021.2

  A convenient method for the preparation of 2-(2-amino-6-oxo-1,4,5,6-tetrahydropyrimidin-5-yl)acetanilides based on the reaction of N-arylitaconimides with various carboximidamides has been proposed. In the course of the transformation, a cascade reaction occurs encompassing the aza-Michael addition of carboximidamides to N-arylitaconimides and the subsequent recyclization of intermediates to dihydropyrimidine

  提出了一种基于N-芳基衣康酰亚胺与各种羧酰亚胺的反应制备2-（2-氨基-6-氧代-1,4,5,6-四氢嘧啶-5-基）乙酰胺的简便方法。在转化过程中，发生级联反应，包括将羧亚胺的氮杂-迈克尔加成至N-芳基亚甲酰亚胺，以及随后将中间体环化成二氢嘧啶对乙酰苯胺。