ethyl 3-(4'-bromophenyl)-4,6-dimethoxyindol-1-ylacetate | 1100050-16-5

• 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: ethyl 3-(4'-bromophenyl)-4,6-dimethoxyindol-1-ylacetate
• 英文别名: Ethyl 2-[3-(4-bromophenyl)-4,6-dimethoxyindol-1-yl]acetate
• CAS: 1100050-16-5
• 化学式: C₂₀H₂₀BrNO₄
• 分子量: 418.287
• InChiKey: PSFYYIDLOQSZBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4'-bromophenyl)-4,6-dimethoxyindol-1-ylacetate 、 N,N-二甲基甲酰胺 在 三氯氧磷 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以81%的产率得到ethyl 3-(4'-bromophenyl)-7-formyl-4,6-dimethoxyindol-1-ylacetate
  参考文献：
  名称：

  Effective synthetic routes to activated pyrrolo[3,2,1-hi]indoles

  摘要：

  Pyrrolo[3,2,1-hi]indoles have been formed by the aldol cyclisation of 7-formyl-N-indolylacetates. The synthetic sequence incorporates three steps from suitably activated indoles: these are alkylation at nitrogen with a bromoacetic ester, formylation at C7 and an aldol condensation between these two substituents. Art X-ray crystal structure of pyrrolo[3,2,1-hi]indole 24 is described. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.025
• 作为产物：
  描述：

  溴乙酸乙酯 、 3-(4-bromophenyl)-4,6-dimethoxy-1H-indole 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 以78%的产率得到ethyl 3-(4'-bromophenyl)-4,6-dimethoxyindol-1-ylacetate
  参考文献：
  名称：

  Effective synthetic routes to activated pyrrolo[3,2,1-hi]indoles

  摘要：

  Pyrrolo[3,2,1-hi]indoles have been formed by the aldol cyclisation of 7-formyl-N-indolylacetates. The synthetic sequence incorporates three steps from suitably activated indoles: these are alkylation at nitrogen with a bromoacetic ester, formylation at C7 and an aldol condensation between these two substituents. Art X-ray crystal structure of pyrrolo[3,2,1-hi]indole 24 is described. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.025

文献信息

• Effective synthetic routes to activated pyrrolo[3,2,1-hi]indoles
  作者：Jumina、Paul A. Keller、Naresh Kumar、David StC. Black

  DOI：10.1016/j.tet.2008.10.025

  日期：2008.12

  Pyrrolo[3,2,1-hi]indoles have been formed by the aldol cyclisation of 7-formyl-N-indolylacetates. The synthetic sequence incorporates three steps from suitably activated indoles: these are alkylation at nitrogen with a bromoacetic ester, formylation at C7 and an aldol condensation between these two substituents. Art X-ray crystal structure of pyrrolo[3,2,1-hi]indole 24 is described. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.