4-bromo-1-(3-methyl-1H-indol-2-yl)butan-1-one | 1419101-67-9

• 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: 4-bromo-1-(3-methyl-1H-indol-2-yl)butan-1-one
• CAS: 1419101-67-9
• 化学式: C₁₃H₁₄BrNO
• 分子量: 280.164
• InChiKey: DHLPSPWPBXBVMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  32.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-bromo-1-(3-methyl-1H-indol-2-yl)butan-1-one 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以95%的产率得到6,7,8,9-tetrahydro,10-methylpyrido<1,2-a>indol-9-one
  参考文献：
  名称：

  Cu(OTf)₂-Catalyzed Synthesis of 2,3-Disubstituted Indoles and 2,4,5-Trisubstituted Pyrroles from α-Diazoketones

  摘要：

  A novel method has been devised for the synthesis of 2,4,5-trisubstituted pyrrole derivatives through the coupling of alpha-diazoketones with beta-enaminoketones and esters using 10 mol % of Cu(OTf)(2). A wide range of 2,3-disubstituted indole derivatives were also prepared from alpha-diazoketones and 2-aminoaryl or alkyl ketones. The synthetic versatility of this approach has been exemplified In the formal synthesis of homofascaplysin C.

  DOI：

  10.1021/ol303206w
• 作为产物：
  描述：

  邻氨基苯乙酮 、 5-Bromo-1-diazopentan-2-one 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以55%的产率得到4-bromo-1-(3-methyl-1H-indol-2-yl)butan-1-one
  参考文献：
  名称：

  Cu(OTf)₂-Catalyzed Synthesis of 2,3-Disubstituted Indoles and 2,4,5-Trisubstituted Pyrroles from α-Diazoketones

  摘要：

  A novel method has been devised for the synthesis of 2,4,5-trisubstituted pyrrole derivatives through the coupling of alpha-diazoketones with beta-enaminoketones and esters using 10 mol % of Cu(OTf)(2). A wide range of 2,3-disubstituted indole derivatives were also prepared from alpha-diazoketones and 2-aminoaryl or alkyl ketones. The synthetic versatility of this approach has been exemplified In the formal synthesis of homofascaplysin C.

  DOI：

  10.1021/ol303206w