1-(4-fuorophenyl)-3-phenyl-1H-pyrrole-2,5-dione | 897014-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 1-(4-fuorophenyl)-3-phenyl-1H-pyrrole-2,5-dione
• 英文别名: 1-(4-fluorophenyl)-3-phenyl-1H-pyrrole-2,5-dione；N-(4-fluorophenyl)-3-phenylmaleimide；1-(4-fluorophenyl)-3-phenylpyrrole-2,5-dione
• CAS: 897014-11-8
• 化学式: C₁₆H₁₀FNO₂
• 分子量: 267.259
• InChiKey: MHORJCWLPPXFHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1-(4-fuorophenyl)-3-phenyl-1H-pyrrole-2,5-dione 在 3,5-二甲基吡唑 作用下， 以 氯苯 为溶剂， 反应 24.0h， 以74.3%的产率得到(3aSR,3bRS,6aSR,10bRS)-2,5-di(4-fluorophenyl)-6a-phenyl-1,2,3,3a,3b,4,5,6,6a,10b-decahydrobenzo[e]pyrrolo[3,4-g]isoindole-1,3,4,6-tetraone
  参考文献：
  名称：

  （4 + 2）在3,5-二甲基-1 H-吡唑和2,6-二甲基吡啶存在下，芳基马来酸酰亚胺化

  摘要：

  在3,5-二甲基-1 H-吡唑存在下，在24小时内于氯苯中加热将芳基马来酸的酰亚胺进行（4 + 2）二聚，得到1,2,3,3a，3b，4,5,6， 6a，10b-十氢苯并[ e ]吡咯并[3,4- g ]异吲哚-1,3,4,6-四酮的收率很好。已确定在100℃下在2，6-二甲基吡啶中芳基马来酸的酰亚胺的加热过程中，获得了含有二甲基吡啶片段的（4 + 2）二聚产物。

  DOI：

  10.1016/j.tet.2010.04.022
• 作为产物：
  描述：

  在 sodium periodate 、 水 、 lithium bromide 作用下， 以 乙腈 为溶剂， 以76%的产率得到1-(4-fuorophenyl)-3-phenyl-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  NaIO4 介导的 γ-内酰胺羧酸的脱羧氧化：一种制备 N-芳基马来酰亚胺衍生物的简单方法

  摘要：

  已经开发了一种简单的方法，用于从 N-芳基 γ-内酰胺-2-羧酸合成 N-芳基马来酰亚胺，通过在回流的乙腈 - 水溶剂中使用氧化剂 NaIO 4 /LiBr 进行脱羧氧化和脱氢。

  DOI：

  10.1055/s-0029-1218379

文献信息

• Palladium-Catalyzed Carbonylative Cyclization of Terminal Alkynes and Anilines to 3-Substituted Maleimides
  作者：Jian-Xing Xu、Xiao-Feng Wu

  DOI：10.1002/adsc.201800672

  日期：2018.9.3

  Herein, we describe an interesting palladium‐catalyzed protocol for the carbonylative synthesis of 3‐substituted maleimides. By annulation of simple anilines with terminal alkynes under carbon monoxide pressure, the desired 3‐substituted maleimides can be obtained in 50–85% yields. Additionally, with the addition of phosphine ligand, maleic acid isoimide can be obtained from the same substrates as

  在这里，我们描述了一个有趣的钯催化方案，用于3-取代的马来酰亚胺的羰基合成。通过在一氧化碳压力下用末端炔烃对简单的苯胺进行环化处理，可以以50-85％的产率获得所需的3-取代的马来酰亚胺。另外，通过添加膦配体，也可以从相同的底物获得马来酸异酰亚胺。在存在K 2 S 2 O 8的情况下，可以将所获得的马来酸异酰亚胺完全转化为相应的马来酰亚胺。
• Palladium-catalyzed aerobic oxidative carbonylation of alkynes with amines: a general access to substituted maleimides
  作者：Ji Yang、Jiawang Liu、Ralf Jackstell、Matthias Beller

  DOI：10.1039/c8cc05802d

  日期：——

  A catalytic oxidative carbonylation reaction was developed for the synthesis of polysubstituted maleimides from alkynes and amines with air as a green oxidant. This novel transformation proceeds in the presence of palladium chloride without the need for expensive ligands or additives and has a broad substrate scope affording a variety of maleimides in good to high yields.

  开发了一种催化氧化羰基化反应，用于以空气为绿色氧化剂由炔烃和胺合成多取代的马来酰亚胺。这种新颖的转化反应在氯化钯的存在下进行，而无需昂贵的配体或添加剂，并且具有广泛的底物范围，可提供各种高至高收率的马来酰亚胺。
• PHENYL SUBSTITUTED MALEIMIDES AS MEDICAMENTS FOR BLOCKING DEGENERATIVE TISSUE DAMAGES BY INHIBITING MPT
  申请人：Pellicci PierGiuseppe

  公开号：US20100099736A1

  公开（公告）日：2010-04-22

  The invention discloses the use of a compound of formula (I), wherein R 1 , R 2 , R 3 , and R 4 each independently represents: hydrogen; halo; hydroxy; (C 1 -C 6 ) alkyl optionally substituted by hydroxy or (C 1 -C 4 ) alkoxy; (C 1 -C 6 ) haloalkyl; (C 1 -C 6 ) alkoxy; and (C 1 -C 6 ) haloalkoxy; for the preparation of a medicament for the prevention and/or treatment of diseases resulting from opening of the MPTP which are characterized by degenerative tissue damages, in particular, diabetes and diabetic complications, neurological diseases and stroke, heart infarction, inherited dystrophies and hepatitis, more particularly, diabetic vascular diseases, such as diabetic retinopathy, and neurodegenerative disorders, such as multiple sclerosis. Further objects are a group of selected individual compounds of formula (I) for use as medicaments and a further group of selected individual compounds of formula (I) as novel compounds.

  本发明揭示了使用公式（I）的化合物，其中R1、R2、R3和R4分别独立地表示：氢；卤素；羟基；（C1-C6）烷基，可选地被羟基或（C1-C4）烷氧基取代；（C1-C6）卤代烷基；（C1-C6）烷氧基；以及（C1-C6）卤代烷氧基；用于制备预防和/或治疗由MPTP开放引起的疾病的药物，这些疾病以组织退行性损伤为特征，特别是糖尿病和糖尿病并发症、神经系统疾病和中风、心脏梗塞、遗传性肌营养不良和肝炎，更具体地说，是糖尿病血管病，如糖尿病视网膜病变，以及神经退行性疾病，如多发性硬化症。进一步的目标是一组选择的公式（I）的单个化合物，用作药物，以及一组选择的公式（I）的单个化合物作为新化合物。
• Palladium‐Catalyzed Tandem Cyclization of Bromoalkynes, Anilines and CO: Access to 1,3‐Substituted Maleimides
  作者：Caijin Zeng、Shaoting Su、Songjia Fang、Huangfeng Jiang、Shaorong Yang、Wanqing Wu

  DOI：10.1002/asia.202300880

  日期：2023.12.14

  A novel palladium‐catalyzed three‐component carbonylation reaction for the assembly of various 1,3‐substituted maleimide derivatives from haloalkynes and simple anilines. The nucleophilic addition reaction of haloalkynes, anilines and CO, and insertion of carbonyl have been achieved sequentially in this reaction. The high chemo‐ and regioselectivities, as well as no need of expensive ligands or additives further illustrate the synthetic value of this approach.

  摘要 一种新型的钯催化三组分羰基化反应，用于从卤代炔类和简单苯胺组装各种 1,3 取代马来酰亚胺衍生物。在该反应中，卤代炔烃、苯胺和 CO 的亲核加成反应以及羰基的插入反应依次实现。高化学选择性和区域选择性以及无需昂贵的配体或添加剂进一步说明了这种方法的合成价值。
• Regioselectivity in the Addition of 1,3-Dipolarophiles to 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes
  作者：A. P. Molchanov、D. I. Sipkin、Yu. B. Koptelov、J. Kopf、R. R. Kostikov

  DOI：10.1023/b:rujo.0000034912.48684.d4

  日期：2004.1

  Thermolysis of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of 1,3-dipolarophiles having an unsymmetrically substituted double Cdouble bondC bond (such as N-arylimides derived from 2-aryl-substituted maleic, citraconic, and itaconic acids, ethyl propynoate, aryl isocyanates, and aryl isothiocyanates) leads to formation of the corresponding 1,3-dipolar cycloaddition products. The reaction is regioselective, and in most cases only one regioisomer is obtained. The addition direction depends on the 1,3-dipolarophile structure, i.e., electronic and steric factors determining the most effective orbital interaction upon approach of the reagent to substrate.