2-(1-benzyl-5-chloro-1H-indol-3-yl)-1-phenylethanone | 1334405-02-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-benzyl-5-chloro-1H-indol-3-yl)-1-phenylethanone
• 英文别名: 2-(1-Benzyl-5-chloroindol-3-yl)-1-phenylethanone
• CAS: 1334405-02-5
• 化学式: C₂₃H₁₈ClNO
• 分子量: 359.855
• InChiKey: XIBOJEAQTBMLID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 scandium tris(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 以73%的产率得到2-(1-benzyl-5-chloro-1H-indol-3-yl)-1-phenylethanone
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed Synthesis of Indoles and SnCl₄-Mediated Regioselective Hydrochlorination of 5-(Arylamino)pent-3-yn-2-ones

  摘要：

  Highly substituted indole derivatives bearing alkyl and aryl moieties can be prepared by Sc(OTf)(3)-catalyzed Friedel-Crafts alkenylation of 5-(arylamino)pent-3-yn-2-ones. In addition, a method for regioselective hydrochlorination of 5-(arylamino)pent-3-yn-2-ones mediated by SnCl4 in moderate to good yields (up to 84%) has been developed. The resulting exclusive Z-selectivity of the C-Cl bond can be further exploited using cross C-N coupling reactions.

  DOI：

  10.1021/jo201514q

文献信息

• Sc(OTf)₃-Catalyzed Synthesis of Indoles and SnCl₄-Mediated Regioselective Hydrochlorination of 5-(Arylamino)pent-3-yn-2-ones
  作者：Fang Yang、Ke-Gong Ji、Shaukat Ali、Yong-Min Liang

  DOI：10.1021/jo201514q

  日期：2011.10.21

  Highly substituted indole derivatives bearing alkyl and aryl moieties can be prepared by Sc(OTf)(3)-catalyzed Friedel-Crafts alkenylation of 5-(arylamino)pent-3-yn-2-ones. In addition, a method for regioselective hydrochlorination of 5-(arylamino)pent-3-yn-2-ones mediated by SnCl4 in moderate to good yields (up to 84%) has been developed. The resulting exclusive Z-selectivity of the C-Cl bond can be further exploited using cross C-N coupling reactions.