ethyl 1-benzyl-2-methyl-4,5-dioxo-4,5-dihydro-1H-benzo[g]indole-3-carboxylate | 66558-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 1-benzyl-2-methyl-4,5-dioxo-4,5-dihydro-1H-benzo[g]indole-3-carboxylate
• 英文别名: 1-Benzyl-2-methyl-3-ethoxycarbonyl-4,5-dioxobenzoxindole；1-benzyl-2-methyl-4,5-dioxo-4,5-dihydro-1H-benzo[g]indole-3-carboxylic acid ethyl ester；Indolcarbonsaureester；ethyl 1-benzyl-2-methyl-4,5-dioxobenzo[g]indole-3-carboxylate
• CAS: 66558-31-4
• 化学式: C₂₃H₁₉NO₄
• 分子量: 373.408
• InChiKey: XNGBUJSADZRFNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 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：
  65.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-benzyl-2-methyl-4,5-dioxo-4,5-dihydro-1H-benzo[g]indole-3-carboxylate 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 以79.4%的产率得到1-Benzyl-2-methyl-3-ethoxycarbonyl-4-carboxy-5-(o-carboxyphenyl)-pyrrole
  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：

  (E)-3-Benzylamino-but-2-enoic acid ethyl ester 在 硝酸 作用下， 以 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 生成 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

文献信息

• 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：——
• 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