2-(1-benzyl-1H-indol-3-yl)-1-phenylethanone | 1334404-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-benzyl-1H-indol-3-yl)-1-phenylethanone
• 英文别名: 2-(1-Benzylindol-3-yl)-1-phenylethanone
• CAS: 1334404-97-5
• 化学式: C₂₃H₁₉NO
• 分子量: 325.41
• InChiKey: VERKXGSEPCYKFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 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42%的产率得到2-(1-benzyl-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

• Benzylic C(sp³)–C(sp²) cross-coupling of indoles enabled by oxidative radical generation and nickel catalysis
  作者：Weonjeong Kim、Jangwoo Koo、Hong Geun Lee

  DOI：10.1039/d0sc06666d

  日期：——

  effectively delivered from an aryl (pseudo)halide or an acid anhydride coupling partner, respectively. The developed method utilizes mild conditions and exhibits a wide substrate scope for both substituted indoles and C(sp2)-based reaction counterparts. Mechanistic studies have shown that competitive hydrogen atom transfer (HAT) processes, which are frequently encountered in conventional methods, are not

  基于吲哚底物的容易氧化事件，开发了一种机械上独特的苄基 C(sp 3 )-H 键功能化策略。这种新颖的途径是通过在底物的苄基位置上有效地产生自由基来启动的，随后通过过渡金属催化来完成整个转化。最终，芳基或酰基可以分别从芳基（拟）卤化物或酸酐偶联配偶体有效地传递。所开发的方法利用温和的条件，并对取代的吲哚和基于 C(sp 2 ) 的反应对应物表现出广泛的底物范围。机理研究表明，传统方法中经常遇到的竞争性氢原子转移（HAT）过程并不参与所开发策略的产物形成过程。
• 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.