2-(4,6-dimethoxy-3-phenylindol-1-yl)-1-phenylethanone | 827024-89-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4,6-dimethoxy-3-phenylindol-1-yl)-1-phenylethanone
• 英文别名: 4,6-dimethoxy-1-phenacyl-3-phenylindole；Ethanone, 2-(4,6-dimethoxy-3-phenyl-1H-indol-1-yl)-1-phenyl-
• CAS: 827024-89-5
• 化学式: C₂₄H₂₁NO₃
• 分子量: 371.436
• InChiKey: QHGYRZMETPNEAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺 、 2-(4,6-dimethoxy-3-phenylindol-1-yl)-1-phenylethanone 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 0.75h， 以69%的产率得到4,6-dimethoxy-1-phenacyl-3-phenylindole-7-carbaldehyde
  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：

  2,2'-((3,5-dimethoxyphenyl)azanediyl)bis(1-phenylethan-1-one) 在 三氟乙酸 作用下， 反应 4.0h， 以87%的产率得到2-(4,6-dimethoxy-3-phenylindol-1-yl)-1-phenylethanone
  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

• Synthesis of activated 3-substituted indoles: an optimised one-pot procedure
  作者：Karin Pchalek、Ashley W. Jones、Monique M.T. Wekking、David StC. Black

  DOI：10.1016/j.tet.2004.10.060

  日期：2005.1

  3-Substituted-4,6-dimethoxyindoles can be synthesised in a one-pot procedure from 3,5-dimethoxyaniline and 2-haloketones in the presence of lithium bromide and sodium bicarbonate. (C) 2004 Elsevier Ltd. All rights reserved.