N-(4-fluorophenyl)itaconimide

• 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-(4-fluorophenyl)itaconimide
• 英文别名: 1-(4-Fluorophenyl)-3-methylidenepyrrolidine-2,5-dione
• 化学式: C₁₁H₈FNO₂
• mdl: MFCD09754287
• 分子量: 205.188
• InChiKey: LYOWWKLHPCUGIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-fluorophenyl)itaconimide 在 氯 作用下， 以 氯仿 、 苯 为溶剂， 生成 (1S,3S)-1-Chloro-5-(4-fluoro-phenyl)-4,6-dioxo-5-aza-spiro[2.4]heptane-1-carboxylic acid methyl ester
  参考文献：
  名称：

  脂肪族重氮化合物的反应：V.重氮乙酸甲酯与衣康酸酰亚胺的反应

  摘要：

  Methyl diazoacetate regioselectively adds to N-substituted imides of itaconic acid to afford 2-pyrazolines, methyl 7-aryl-6,8-dioxo-1,2,7-triazaspiro[4.4]non-2-ene-3-carboxylates that in reaction with halogens (Cl-2, Br-2) yield methyl 5-aryl-1-halo-4,6-dioxo-5-azaspiro[2.4]heptane-1-carboxylates as a mixture of syn- and anti$(2$)-isomers.

  DOI：

  10.1023/a:1015534221121

文献信息

• Acid-induced rearrangement of cycloadducts from N-aryl itaconimides and 1,3-diphenylisobenzofuran
  作者：Alexander V. Stepakov、Vitaly M. Boitsov、Anna G. Larina、Alexander P. Molchanov

  DOI：10.1016/j.tetlet.2014.06.107

  日期：2014.8

  Treatment of several Diels–Alder adducts of N-aryl itaconimides and 1,3-diphenylisobenzofuran with a strong acid triggers a skeletal rearrangement resulting in 2-aryl-6,10b-diphenylbenzo[h]isoquinoline-1,3(2H,10bH)-diones.

  用强酸处理N-芳基衣康酰亚胺和1,3-二苯基异苯并呋喃的几种Diels-Alder加合物会引起骨骼重排，从而导致2-芳基-6,10b-二苯基苯并[ h ]异喹啉-1,3（2 H，10b H）-二酮。
• 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。
• Stereoselective cycloaddition of diphenylisobenzofuran to N-arylitaconimides
  作者：A. P. Molchanov、A. V. Stepakov、V. M. Boitsov、R. R. Kostikov

  DOI：10.1007/s11172-013-0138-6

  日期：2013.4

  A reaction of 1,3-diphenylisobenzofuran with N-arylitaconimides gives the [4+2] cycloaddition products with the 11′-oxaspiro[pyrrolidine-3,9′-tricyclo[6.2.1.0 2,7 ]undeca-2′,4′,6′-triene-2,5-dione] skeleton as a single diastereomer.

  1,3-二苯基异苯并呋喃与N-芳基衣康酰亚胺的反应得到单一的非对映异构体的[4+2]环加成产物，其骨架为11′-氧杂螺[吡咯烷-3,9′-三环[6.2.1.0 2,7]十一碳-2′,4′,6′-三烯-2,5-二酮]。
• 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。
• Access to Isoxazolidines through Visible-Light-Induced Difunctionalization of Alkenes
  作者：Hui Yang、Guo Wei、Zhiyong Jiang

  DOI：10.1021/acscatal.9b03567

  日期：2019.10.4

  decarboxylation of N-aryl glycines are added to alkenes and the resulting radical intermediates are trapped by superoxides. The peroxides undergo swift intramolecular amine oxidation to provide the valuable isoxazolidines. Alkenes with varied functionalization can be applied. The isoxazolidine ring can be readily opened via reduction by zinc in acetic acid to afford γ-lactams in high yield.

  据报道，具有特征在于可见光诱导的烯烃的需氧双官能化的异恶唑烷的获得。通过N-芳基甘氨酸的氧化脱羧反应生成的α-氨基自由基被添加到烯烃中，并且自由基中间体被超氧化物捕获。过氧化物进行快速的分子内胺氧化以提供有价值的异恶唑烷。可以应用具有不同功能的烯烃。通过在乙酸中用锌还原可容易地打开异恶唑烷环，从而以高收率提供γ-内酰胺。