1-acetyl-2,7-dibromo-4,6-dimethoxy-3-phenylindole | 1396790-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-acetyl-2,7-dibromo-4,6-dimethoxy-3-phenylindole
• 英文别名: 1-(2,7-Dibromo-4,6-dimethoxy-3-phenylindol-1-yl)ethanone；1-(2,7-dibromo-4,6-dimethoxy-3-phenylindol-1-yl)ethanone
• CAS: 1396790-18-3
• 化学式: C₁₈H₁₅Br₂NO₃
• 分子量: 453.13
• InChiKey: FIGOWBHIKZQNRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1-acetyl-2,7-dibromo-4,6-dimethoxy-3-phenylindole 在 甲醇 、 potassium hydroxide 作用下， 反应 0.75h， 以80%的产率得到2,7-dibromo-4,6-dimethoxy-3-phenylindole
  参考文献：
  名称：

  Bromination of 4,6-dimethoxyindoles

  摘要：

  The bromination of activated 4,6-dimethoxyindoles can be carried out effectively provided that an electron-withdrawing group is also present. Thus the range of products includes 2-bromo-7-formyl or 2-bromo-7-acetylindoles 13a-c and 16, 7-bromo-2-acetylindole 21, 2,5-dibromo-7-acetylindole 17, 2,5-dibromo-N-sulfonylindole 27, and 2,7-dibromo-N-acetylindole 24. Acetyl and sulfonyl protecting groups on nitrogen can be removed to give 2-bromoindoles 28a-b, 2,5-dibromoindole 29, and 2,7-dibromoindole 4. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.077
• 作为产物：
  描述：

  4,6-二甲氧基-3-苯基-1-乙酰基吲哚 在 N-溴代丁二酰亚胺(NBS) 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以60%的产率得到1-acetyl-2,7-dibromo-4,6-dimethoxy-3-phenylindole
  参考文献：
  名称：

  Bromination of 4,6-dimethoxyindoles

  摘要：

  The bromination of activated 4,6-dimethoxyindoles can be carried out effectively provided that an electron-withdrawing group is also present. Thus the range of products includes 2-bromo-7-formyl or 2-bromo-7-acetylindoles 13a-c and 16, 7-bromo-2-acetylindole 21, 2,5-dibromo-7-acetylindole 17, 2,5-dibromo-N-sulfonylindole 27, and 2,7-dibromo-N-acetylindole 24. Acetyl and sulfonyl protecting groups on nitrogen can be removed to give 2-bromoindoles 28a-b, 2,5-dibromoindole 29, and 2,7-dibromoindole 4. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.077

文献信息

• Bromination of 4,6-dimethoxyindoles
  作者：Peter S.R. Mitchell、Ibrahim F. Sengul、Hakan Kandemir、Stephen J. Nugent、Rui Chen、Paul K. Bowyer、Naresh Kumar、David StC. Black

  DOI：10.1016/j.tet.2012.07.077

  日期：2012.9

  The bromination of activated 4,6-dimethoxyindoles can be carried out effectively provided that an electron-withdrawing group is also present. Thus the range of products includes 2-bromo-7-formyl or 2-bromo-7-acetylindoles 13a-c and 16, 7-bromo-2-acetylindole 21, 2,5-dibromo-7-acetylindole 17, 2,5-dibromo-N-sulfonylindole 27, and 2,7-dibromo-N-acetylindole 24. Acetyl and sulfonyl protecting groups on nitrogen can be removed to give 2-bromoindoles 28a-b, 2,5-dibromoindole 29, and 2,7-dibromoindole 4. (C) 2012 Elsevier Ltd. All rights reserved.