1-Benzyl-2-methyl-3-carbethoxy-5-hydroxybenzindole | 66558-33-6

• 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: 1-Benzyl-2-methyl-3-carbethoxy-5-hydroxybenzindole
• 英文别名: ethyl 1-benzyl-5-hydroxy-2-methyl-1H-benzo[g]indole-3-carboxylate；1-benzyl-5-hydroxy-2-methyl-1H-benzo[g]indole-3-carboxylic acid ethyl ester；ethyl 1-benzyl-5-hydroxy-2-methylbenzo[g]indole-3-carboxylate
• CAS: 66558-33-6
• 化学式: C₂₃H₂₁NO₃
• mdl: MFCD01953997
• 分子量: 359.425
• InChiKey: SOCBBLVJDXLXSN-UHFFFAOYSA-N

物化性质

• 熔点：
  240-241 °C
• 沸点：
  586.0±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Benzyl-2-methyl-3-carbethoxy-5-hydroxybenzindole 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 以83%的产率得到ethyl 1-benzyl-2-methyl-4,5-dioxo-4,5-dihydro-1H-benzo[g]indole-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological activity of 4-oxoindeno[1,2-b]pyrroles

  摘要：

  DOI：

  10.1007/bf00763415
• 作为产物：
  描述：

  乙酰乙酸乙酯 在 溶剂黄146 、 zinc(II) iodide 作用下， 反应 1.67h， 生成 1-Benzyl-2-methyl-3-carbethoxy-5-hydroxybenzindole
  参考文献：
  名称：

  环戊基甲基醚中锌、铁和镁盐的 Nenitzescu 合成 5-羟基吲哚

  摘要：

  在环戊基甲基醚 (CPME) 中，烯胺和醌的 Nenitzescu 反应可以在室温下与 ZnCl 2、ZnI 2、Mg(CF 3 SO 3 ) 2或 FeCl 3催化得到 5-羟基吲哚结晶固体，它可以通过简单过滤从反应混合物中分离。CPME 可以有效回收和再利用。

  DOI：

  10.1002/ejoc.202101045

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。
• A new CAN-catalyzed domino process related to the Nenitzescu reaction: very concise access to fused ortho-indolequinones from simple precursors
  作者：Padmakar A. Suryavanshi、Vellaisamy Sridharan、J. Carlos Menéndez

  DOI：10.1016/j.tet.2013.04.101

  日期：2013.7

  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.
• GRINEV, A. N.;MIXAJLOVA, I. N.;NIKOLAEVA, I. S.;GOLOVANOVA, E. A.;POLUXIN+, XIM.-FARMATS. ZH., 1982, 16, N 4, 433-438
  作者：GRINEV, A. N.、MIXAJLOVA, I. N.、NIKOLAEVA, I. S.、GOLOVANOVA, E. A.、POLUXIN+

  DOI：——

  日期：——
• Nenitzescu Synthesis of 5‐Hydroxyindoles with Zinc, Iron and Magnesium Salts in Cyclopentyl Methyl Ether
  作者：Giuseppe Satta、Elena Usala、Angelo Solinas、Melina Römer、Marco Livesi、Giovanni Michele Pira、Andrea Beccu、Silvia Carboni、Silvia Gaspa、Lidia De Luca、Luisa Pisano、Ugo Azzena、Massimo Carraro

  DOI：10.1002/ejoc.202101045

  日期：2021.11.15

  In cyclopentyl methyl ether (CPME), the Nenitzescu reaction of enamines and quinones can be catalyzed with ZnCl2, ZnI2, Mg(CF3SO3)2 or FeCl3 at room temperature to give 5-hydroxyindoles as crystalline solids, which can be isolated by simple filtration from the reaction mixture. CPME can be efficiently recycled and reused.

  在环戊基甲基醚 (CPME) 中，烯胺和醌的 Nenitzescu 反应可以在室温下与 ZnCl 2、ZnI 2、Mg(CF 3 SO 3 ) 2或 FeCl 3催化得到 5-羟基吲哚结晶固体，它可以通过简单过滤从反应混合物中分离。CPME 可以有效回收和再利用。
• Synthesis and biological activity of 4-oxoindeno[1,2-b]pyrroles
  作者：A. N. Grinev、I. N. Mikhailova、I. S. Nikolaeva、E. A. Golovanova、L. M. Polukhina、G. N. Pershin

  DOI：10.1007/bf00763415

  日期：1982.4