1-benzyl-3-bromo-4-(1H-indol-1-yl)-1H-pyrrole-2,5-dione | 570431-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-benzyl-3-bromo-4-(1H-indol-1-yl)-1H-pyrrole-2,5-dione
• 英文别名: 1-benzyl-3-bromo-4-(indol-1-yl)maleimide；1H-Pyrrole-2,5-dione, 3-bromo-4-(1H-indol-1-yl)-1-(phenylmethyl)-；1-benzyl-3-bromo-4-indol-1-ylpyrrole-2,5-dione
• CAS: 570431-83-3
• 化学式: C₁₉H₁₃BrN₂O₂
• 分子量: 381.228
• InChiKey: VLDXLCYUQAKHCO-UHFFFAOYSA-N

物化性质

• 沸点：
  417.2±45.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  42.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-bromo-4-(1H-indol-1-yl)-1H-pyrrole-2,5-dione 在 sodium carbonate 、 叔丁基二甲基氯硅烷 、 三苯基膦 、 sodium iodide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 19.0h， 生成 1-benzyl-3-indol-1-yl-4-(2-oxo-1H-pyridin-3-yl)pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis and cyclometalation of a pyrido[3,2-e]-2,10b-diaza-cyclopenta[c]fluorene-1,3-dione scaffold

  摘要：

  The synthesis of a pyrido[3,2-e]-2, 10b-diaza-cyclopenta[c]fluorene-1, 3-dione scaffold is disclosed, which was synthesized using a Suzuki cross-coupling reaction and an intramolecular Heck cyclization as the key steps. This heterocyclic system can serve as a bidentate ligand as demonstrated by the formation and structural analysis of a derived ruthenium complex. The new scaffold constitutes an interesting candidate for the development of organometallic protein kinase inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.054
• 作为产物：
  描述：

  N-苄基-2,3-二溴马来酰亚胺 在 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 1-benzyl-3-bromo-4-(1H-indol-1-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Introduction of pharmacophore groups into bis(indol-1-yl)maleimides and 6H-pyrrolo[3,4: 2,3][1,4]diazepino[6,7,1-hi]-indolo-8,10(7H,9H)-diones

  摘要：

  描述了一种合成含有各种官能团的双(吲哚-1-基)马来酰亚胺和聚合[1,4]二氮杂卓的方法，这些化合物是生物活性吲哚[2,3-à]咔唑的类似物。通过使用含有这些官能团的前体，直接在[1,4]二氮杂卓和双(吲哚-1-基)马来酰亚胺分子中引入官能团，利用亲电取代反应实现。

  DOI：

  10.1007/s11094-006-0147-y

文献信息

• Synthesis of 6H-pyrrolo[3′,4′:2,3][1,4]diazepino[6,7,1-hi]indole-8,10(7H,9H)-diones using 3-bromo-4-(indol-1-yl)maleimide scaffold
  作者：Sergey A. Lakatosh、Yuri N. Luzikov、Maria N. Preobrazhenskaya

  DOI：10.1039/b211163b

  日期：2003.2.27

  Series of 3-arylalkyl- or 3-alkylamino-4-(indol-1-yl)maleimides and bis(indol-1-yl)maleimides were synthesised. The cyclization of the 3-substituted 4-(indol-1-yl)maleimides under the action of acids resulted in the formation of diazepine[1,4] derivatives with indoline and maleimide nuclei annelated. These compounds readily produced the corresponding indolomaleimidodiazepines[1,4] after dehydrogenation.

  合成了一系列 3-芳烷基或 3-烷基氨基-4-(吲哚-1-基)马来酰亚胺和双(吲哚-1-基)马来酰亚胺。在酸的作用下，3-取代的 4-(吲哚-1-基)马来酰亚胺环化，形成了吲哚啉和马来酰亚胺核环化的二氮杂卓[1,4]衍生物。这些化合物在脱氢后很容易生成相应的吲哚马来酰亚胺二氮杂卓[1,4]。
• Diazepines[1,4] annelated with indoline and maleimide from 3-(di)alkylamino-4-(indol-1-yl)maleimides: mechanism of rearrangement and cyclization
  作者：Sergey A. Lakatosh、Yuri N. Luzikov、Maria N. Preobrazhenskaya

  DOI：10.1016/j.tet.2005.01.005

  日期：2005.2

  The mechanism of cyclization of 3-(di)alkylamino-4-(indol-1-yl)maleimides to diazepine[1,4] derivatives was elucidated using deuterium labeled precursors. (C) 2005 Published by Elsevier Ltd.
• Introduction of pharmacophore groups into bis(indol-1-yl)maleimides and 6H-pyrrolo[3,4: 2,3][1,4]diazepino[6,7,1-hi]-indolo-8,10(7H,9H)-diones
  作者：S. A. Lakatosh、A. Yu. Simonov、Yu. N. Luzikov、M. N. Preobrazhenskaya

  DOI：10.1007/s11094-006-0147-y

  日期：2006.8

  The synthesis of bis(indol-1-yl)maleimides and polycondensed [1,4]diazepines containing various functional groups, which are the analogs of biologically active indolo[2,3-à]carbazoles, is described. Functional groups were introduced directly into [1,4]diazepine and bis(indol-1-yl)maleimide molecules via electrophilic substitution reactions using precursors containing such functional groups.

  描述了一种合成含有各种官能团的双(吲哚-1-基)马来酰亚胺和聚合[1,4]二氮杂卓的方法，这些化合物是生物活性吲哚[2,3-à]咔唑的类似物。通过使用含有这些官能团的前体，直接在[1,4]二氮杂卓和双(吲哚-1-基)马来酰亚胺分子中引入官能团，利用亲电取代反应实现。
• Synthesis and cyclometalation of a pyrido[3,2-e]-2,10b-diaza-cyclopenta[c]fluorene-1,3-dione scaffold
  作者：Seann P. Mulcahy、Patrick J. Carroll、Eric Meggers

  DOI：10.1016/j.tetlet.2006.10.054

  日期：2006.12

  The synthesis of a pyrido[3,2-e]-2, 10b-diaza-cyclopenta[c]fluorene-1, 3-dione scaffold is disclosed, which was synthesized using a Suzuki cross-coupling reaction and an intramolecular Heck cyclization as the key steps. This heterocyclic system can serve as a bidentate ligand as demonstrated by the formation and structural analysis of a derived ruthenium complex. The new scaffold constitutes an interesting candidate for the development of organometallic protein kinase inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.