N-(1-(4-bromophenyl)-1-(3-indolyl)ethyl)acetamide | 1312598-96-1

• 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: N-(1-(4-bromophenyl)-1-(3-indolyl)ethyl)acetamide
• 英文别名: N-[1-(4-bromophenyl)-1-(1H-indol-3-yl)ethyl]acetamide
• CAS: 1312598-96-1
• 化学式: C₁₈H₁₇BrN₂O
• 分子量: 357.25
• InChiKey: SNMDQECVHJMFBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 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：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吲哚 、 N-[1-(4-溴苯基)乙烯基]乙酰胺 在 C₈₆H₈₅O₄P₃⁽²⁺⁾*2F₆P^(1-) 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以94%的产率得到N-(1-(4-bromophenyl)-1-(3-indolyl)ethyl)acetamide
  参考文献：
  名称：

  Phosphonium ion tagged chiral phosphoric acids and their application in Friedel–Crafts reactions of indoles

  摘要：

  The attachment of phosphonium ion phase tags to chiral binapthyl-based phosphoric acid catalysts, and the use of these materials in a range of organocatalytic asymmetric Friedel-Crafts reactions of indoles has been studied. Placement of the tags at the 3 and 3' positions of the phosphoric acid, so that they could serve as steric blocking groups, failed to produce an active catalyst. However, moving the phosphonium ion groups to the 6 and 6' positions produced an efficient and enantioselective catalyst. Aided by the presence of the phase tags, the chiral catalyst was easily removed at the end of the reactions, and could be reused several times, albeit with somewhat decreased efficiency and enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.105

文献信息

• Chiral Brønsted Acid Catalyzed Enantioselective Friedel–Crafts Reaction of Indoles and α-Aryl Enamides: Construction of Quaternary Carbon Atoms
  作者：Yi-Xia Jia、Jun Zhong、Shou-Fei Zhu、Can-Ming Zhang、Qi-Lin Zhou

  DOI：10.1002/anie.200701067

  日期：2007.7.16