N-acetyl-α-(5-bromo-1H-indol-3-yl)alanine methyl ester | 1034402-49-7

• 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-acetyl-α-(5-bromo-1H-indol-3-yl)alanine methyl ester
• 英文别名: methyl 2-acetamido-2-(5-bromo-1H-indol-3-yl)propanoate
• CAS: 1034402-49-7
• 化学式: C₁₄H₁₅BrN₂O₃
• 分子量: 339.189
• InChiKey: BYFUWDWDXDVGEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-溴吲哚 、 2-乙酰胺基丙烯酸甲酯 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以61%的产率得到N-acetyl-α-(5-bromo-1H-indol-3-yl)alanine methyl ester
  参考文献：
  名称：

  Switchable Reactivity of Acylated α, β-Dehydroamino Ester in the Friedel−Crafts Alkylation of Indoles by Changing the Lewis Acid

  摘要：

  Highly regioselective electrophilic substitution of indoles with N-acetylated alpha,beta-dehydroalanine methyl ester, promoted by different transition metal salts was achieved. The orthogonal regioselectivity provides an efficient protocol toward highly functionalized 3-indolyl-alpha-amino acids. The mechanism of the reactions was explored by NMR studies.

  DOI：

  10.1021/jo800881u

文献信息

• Switchable Reactivity of Acylated α, β-Dehydroamino Ester in the Friedel−Crafts Alkylation of Indoles by Changing the Lewis Acid
  作者：Elena Angelini、Cesarino Balsamini、Francesca Bartoccini、Simone Lucarini、Giovanni Piersanti

  DOI：10.1021/jo800881u

  日期：2008.7.1

  Highly regioselective electrophilic substitution of indoles with N-acetylated alpha,beta-dehydroalanine methyl ester, promoted by different transition metal salts was achieved. The orthogonal regioselectivity provides an efficient protocol toward highly functionalized 3-indolyl-alpha-amino acids. The mechanism of the reactions was explored by NMR studies.
• Organocatalytic synthesis of α-quaternary amino acid derivatives via aza-Friedel–Crafts alkylation of indoles with simple α-amidoacrylates
  作者：Marika Righi、Francesca Bartoccini、Simone Lucarini、Giovanni Piersanti

  DOI：10.1016/j.tet.2011.08.039

  日期：2011.10

  The first (organo)catalytic method for regio- and chemoselective aza-Friedel-Crafts (FC) alkylation of indoles and pyrroles with commercially available methyl alpha-acetamidoacrylates has been discovered. It minimizes/eliminates common competing reactions that occur due to the high and multiatom-nucleophilic character of indole and pyrrole. Diverse quaternary alpha-amino acids were successfully prepared in good yield and high selectivity using low catalyst loading. The enantioselective variant using BINOL-derived phosphoric acids was also explored with indole providing the desired F-C alkylation product with moderate enantioselectivities. (C) 2011 Elsevier Ltd. All rights reserved.