3-(4-Methoxyanilino)-N-methylmaleimide | 303190-38-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(4-Methoxyanilino)-N-methylmaleimide
• 英文别名: 3-(4-methoxyphenyl)amino-1-methyl-1H-pyrrole-2,5-dione；1-methyl-3-{[4-(methyloxy)phenyl]amino}-1H-pyrrole-2,5-dione；3-(4-methoxyanilino)-1-methylpyrrole-2,5-dione
• CAS: 303190-38-7
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: JPMGEMKZBDUYOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-Methoxyanilino)-N-methylmaleimide 以 三氟乙酸 为溶剂， 反应 1.5h， 以74%的产率得到8-Methoxy-2-methyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,4-c]quinoline-1,3-dione-4-spiro-3'-(1-methylpyrrolidine-2',5'-dione)
  参考文献：
  名称：

  Acid-induced dimerization of 3-(1H-indol-3-yl)maleimides. Formation of cyclopentindole derivatives

  摘要：

  酸诱导的3-取代马来酰亚胺二聚反应已被研究，由此例如以良好产率获得了环戊并吲哚9及深色螺环化合物24和25。3-(1H-吲哚-3-基)马来酰亚胺6b在处理适当的亲二烯体后，容易得到环加成产物13-15。此外，还制备并研究了若干相关的3,3-二(1H-吲哚-3-基)琥珀酰亚胺。

  DOI：

  10.1039/b004030o
• 作为产物：
  描述：

  甲氧苯胺 以 乙醚 为溶剂， 反应 25.0h， 生成 3-(4-Methoxyanilino)-N-methylmaleimide
  参考文献：
  名称：

  Acid-induced dimerization of 3-(1H-indol-3-yl)maleimides. Formation of cyclopentindole derivatives

  摘要：

  酸诱导的3-取代马来酰亚胺二聚反应已被研究，由此例如以良好产率获得了环戊并吲哚9及深色螺环化合物24和25。3-(1H-吲哚-3-基)马来酰亚胺6b在处理适当的亲二烯体后，容易得到环加成产物13-15。此外，还制备并研究了若干相关的3,3-二(1H-吲哚-3-基)琥珀酰亚胺。

  DOI：

  10.1039/b004030o

文献信息

• Molecular Diversity of Three-Component Reaction of<i>β</i>-Enamino Imide, Malononitrile and Cyclic<i>α</i>-Diketones
  作者：Man Xiao、Chaoguo Yan

  DOI：10.1002/cjoc.201700142

  日期：2017.9

  molecular diversity. The reactions with acenaphthylene‐1,2‐dione and ninhydrin afforded functionalized spiro[indene‐2,4'‐pyrrolo[3,4‐b]pyridines] and spiro[acenaphthylene‐1,4'‐pyrrolo[3,4‐b]pyridines] in good yields. The similar reaction of phenanthrene‐9,10‐dione resulted in the formation of the unexpected complex phenanthro[9',10':4,5]furo[2,3‐c]pyrrolo[3,4‐b]pyrroles in satisfactory yields.

  碱促进了β-烯氨基酰亚胺，丙二腈和乙腈中各种环状α-二酮的三组分反应，显示出有趣的分子多样性。与1,2-二酮和茚三酮的反应得到官能化的螺[茚-2,4'-吡咯[3,4- b ]吡啶]和螺[[-1,4'-吡咯[3,4- b] [吡啶]]。菲-9,10-二酮的相似反应导致令人满意的未预期的复杂菲咯[9'，10'：4,5]呋喃[2,3- c ]吡咯并[3,4- b ]吡咯的形成产量。
• Convenient synthesis of functionalized pyrrolo[3,4-b]pyridines and pyrrolo[3,4-b]quinolines via three-component reactions
  作者：Yan-Hong Jiang、Man Xiao、Chao-Guo Yan

  DOI：10.1039/c6ra03165j

  日期：——

  construction of pyrrolo[3,4-b]pyridine skeleton was successfully developed by base promoted three-component reaction of β-enamino imide, aromatic aldehydes and malononitrile as well as its ester and amide derivatives. The similar three-component reaction of β-enamino imide, aromatic aldehydes and cyclic diketones such as dimedone and cyclohexane-1,3-dione afforded functionalized pyrrolo[3,4-b]quinolines in good

  通过β-烯氨基酰亚胺，芳族醛和丙二腈及其酯和酰胺衍生物的碱促进三组分反应，成功开发了一种简便的吡咯并[3,4- b ]吡啶骨架结构。β-烯氨基酰亚胺，芳族醛和环状二酮（如二甲酮和环己烷-1,3-二酮）的类似三组分反应以高收率提供了官能化的吡咯并[3,4- b ]喹啉。
• An Efficient Synthesis of Spiropyrroloquinolines by the Domino Reaction of α-Dicarbonyl Compounds and Anilinosuccinimides
  作者：Man Xiao、Qiu Sun、Jing Sun、Chao-Guo Yan

  DOI：10.1002/ejoc.201701356

  日期：2017.12.15

  Under the catalysis of Bronsted acid, the domino annulation reaction of different α-dicarbonyl compounds with anilinosuccinimides under microwave irradiation afforded functionalized spiropyrroloquinolines involving the activation of ortho-H in different aniline derivatives.

  在布朗斯台德酸的催化下，不同的 α-二羰基化合物与苯胺基琥珀酰亚胺在微波辐射下的多米诺环化反应得到了功能化的螺吡咯并喹啉，涉及活化不同苯胺衍生物中的邻位 H。
• DBU-Catalyzed Highly Efficient Synthesis of 1,4-Dihydropyridine Derivatives from Arylidenemalononitriles and β-Enamino Imides
  作者：Takeshi Oriyama、Wei Han、Kazuya Nakajima、Masashi Kajitani

  DOI：10.3987/com-20-14382

  日期：——

  Various 1,4-dihydropyridine derivatives were efficiently synthesized from arylidenemalononitriles and β-enamino imides using DBU (3 mol%) as the catalyst at room temperature. This mild, straightforward high-yielding protocol was atom-economy, time-economy, with a low catalyst load, and without the need for reflux.

  在室温下，使用DBU（3 mol％）作为催化剂，由芳基丙二腈和β-烯氨基酰亚胺有效地合成了各种1,4-二氢吡啶衍生物。这种温和，简单，高产的方案是原子经济，时间经济，催化剂负载低且无需回流。
• Nucleophilic Phosphine-Promoted Domino Reaction of Dialkyl Acetylenedicarboxylates and 3-Arylamino-1-methyl-1H-pyrrole-2,5-diones
  作者：Ying Han、Chao-Guo Yan、Chang-Zhou Liu、Yuan-Yuan Zhang、Jing Sun

  DOI：10.1055/s-0037-1610438

  日期：2018.9

  ates in satisfactory yields. The three-component reaction of triphenylphosphine, dimethyl acetylenedicarboxylate and 3-arylamino-1-methyl-1H-pyrrole-2,5-diones in CH2Cl2 at room temperature resulted in functionalized 3-(triphenyl-λ5-phosphanylidene)succinates in nearly quantitative yields. However, tri(n-butyl)phosphine promoted reaction of dialkyl acetylenedicarboxylates and 3-arylamino-1-methyl-1H-pyrrole-2

  摘要 三苯基膦的三组分反应，乙炔二和三芳基氨基-1-甲基- 1 H ^ -吡咯-2,5-二酮在CH 2氯2在室温下导致官能3-（三苯基-λ 5 -phosphanylidene）琥珀酸酯的收率接近定量。然而，三（正丁基）膦在CH 2 Cl 2中促进了乙炔二羧酸二烷基酯与3-芳基氨基-1-甲基-1 H-吡咯-2,5-二酮的反应，提供了官能化的吡咯并[3,4- b ]吡啶- 4-羧酸盐具有令人满意的产率。 三苯基膦的三组分反应，乙炔二和三芳基氨基-1-甲基- 1 H ^ -吡咯-2,5-二酮在CH 2氯2在室温下导致官能3-（三苯基-λ 5 -phosphanylidene）琥珀酸酯的收率接近定量。然而，三（正丁基）膦在CH 2 Cl 2中促进了乙炔二羧酸二烷基酯与3-芳基氨基-1-甲基-1 H-吡咯-2,5-二酮的反应，提供了官能化的吡咯并[3,4- b ]吡啶- 4-羧酸盐具有令人满意的产率。