N-(3-chlorophenyl)-itaconimide | 2593-51-3

• 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-(3-chlorophenyl)-itaconimide
• 英文别名: 1-(3-Chlorophenyl)-3-methylidenepyrrolidine-2,5-dione
• CAS: 2593-51-3
• 化学式: C₁₁H₈ClNO₂
• mdl: MFCD29912275
• 分子量: 221.643
• InChiKey: RBZUQLXAEPRQHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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-(3-chlorophenyl)-itaconimide 在 三氟过氧乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以83%的产率得到5-(3-chlorophenyl)-1-oxa-5-azaspiro<2.4>heptane-4,6-dione
  参考文献：
  名称：

  Svetlik, Jan; Veverka, Miroslav, Liebigs Annalen der Chemie, 1990, # 1, p. 111 - 112

  摘要：

  DOI：

文献信息

• Facile One-Pot Synthesis of Benzo[h]isoquinolines via Strong Acid Triggered [1,2]-Sigmatropic Rearrangement: A Theoretical and Experimental Studies
  作者：V.M. Boitsov、N.A. Knyazev、S.V. Shmakov、S.Yu. Vyazmin、D.M. Nikolaev、O.B. Chakchir、A.V. Stepakov

  DOI：10.14233/ajchem.2019.22074

  日期：2019.8.10

  to this ring system has been reported yet. Herein, a facile one-pot synthesis from N-aryl itaconimides and 1,3-diarylisobenzofuran via strong acid triggered skeletal rearrangement reaction is described. Theoretical study for this rearrangement is provided at M11/cc-pVDZ level of theory. Antitumor activity of obtained benzo[h]isoquinoline derivatives against human erythroleukemia K562 cell line was evaluated

  苯并[h]异喹啉支架作为刚性亚基而备受关注，可用于构建生物活性产品。然而，尚未报道该环系统的高产率合成途径。本文描述了通过强酸引发的骨架重排反应从 N-芳基衣康酰亚胺和 1,3-二芳基异苯并呋喃进行简单的一锅合成。在 M11/cc-pVDZ 理论水平上提供了这种重排的理论研究。通过MTS测定评估了所获得的苯并[h]异喹啉衍生物对人红白血病K562细胞系的体外抗肿瘤活性。
• Organocatalytic Asymmetric Tandem Conjugate Addition–Protonation of Azlactones to N-Itaconimides
  作者：Xiaowei Zhao、Zhiyong Jiang、Gao Zhang、Yanli Yin

  DOI：10.1055/s-0036-1588960

  日期：2017.7

  An unprecedented catalytic asymmetric reaction between azlactones and N -itaconimides has been developed. In the presence of an l - tert -leucine-based urea–tertiary amine Bronsted base catalyst, the tandem conjugate addition–protonation products could be attained in moderate yields with excellent enantio- and diastereoselectivities (up to 99% ee and >20:1 dr). The method provides an efficient approach

  已经开发出一种前所未有的吖内酯和 N-衣康酰亚胺之间的催化不对称反应。在 l-叔-亮氨酸基脲-叔胺布朗斯台德碱催化剂存在下，串联共轭加成-质子化产物可以中等产率获得，具有优异的对映选择性和非对映选择性（高达 99% ee 和 >20:1博士）。该方法提供了一种有效的方法来获取有价值的手性 γ-叔胺取代的含有不相邻立体中心的琥珀酰亚胺。
• 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。