methyl 1-butyl-5-hydroxy-2-methyl-1H-benzo[g]indole-3-carboxylate | 1238312-99-6

• 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: methyl 1-butyl-5-hydroxy-2-methyl-1H-benzo[g]indole-3-carboxylate
• 英文别名: Methyl 1-butyl-5-hydroxy-2-methylbenzo[g]indole-3-carboxylate
• CAS: 1238312-99-6
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: KGMZHMYBXYNEGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-methyl 3-(butylamino)-2-(1,4-dioxo-1,4-dihydro-naphth-2-yl)but-2-enoate 在 ammonium cerium (IV) nitrate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以58%的产率得到methyl 1-butyl-2-methyl-4,5-dioxo-4,5-dihydro-1H-benzo[g]indole-3-carboxylate
  参考文献：
  名称：

  A new CAN-catalyzed domino process related to the Nenitzescu reaction: very concise access to fused ortho-indolequinones from simple precursors

  摘要：

  The CAN-catalyzed three-component reaction between primary amines, beta-ketoesters and naphthoquinone in ethanol at room temperature afforded as the main products the corresponding Michael adducts, oxidized to the quinone stage. When these compounds were refluxed in ethanol in the presence of CAN, they afforded tricyclic ortho-quinones derived from the benzo[g]indole-4,5-dione framework via a domino mechanism comprising a sequence of 5-exo-trig cyclization, elimination, Michael addition, oxo-enol tautomerism and hydroquinone oxidation individual steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.101

文献信息

• Expedient, one-pot preparation of fused indoles via CAN-catalyzed three-component domino sequences and their transformation into polyheterocyclic compounds containing pyrrolo[1,2-a]azepine fragments
  作者：Padmakar A. Suryavanshi、Vellaisamy Sridharan、J. Carlos Menéndez

  DOI：10.1039/c004703a

  日期：——

  The CAN-catalyzed three-component between reaction between primary amines, β-dicarbonyl compounds and naphthoquinones or 2-bromonaphthoquinones afforded, respectively, 5-hydroxybenzo[g]indoles and benzo[f]indole-4,9-diones, the former of which were transformed into tetracyclic azepino[1,2-a]benzo[g]indole systems through a γ-alkylation/ring-closing metathesis sequence.

  这 能够伯胺之间的反应之间催化的三组分， β-二羰基化合物和萘醌或2-溴萘醌分别提供了5-羟基苯并[ g ]吲哚和苯并[ f ]吲哚-4,9-二酮，它们的前者转化为四环氮杂[1,2- a ]苯并[ g ]吲哚 系统通过γ-烷基化/闭环复分解序列。