2-amino-3-(5-borono-1H-indol-3-yl)propanoic acid | 1240784-16-0

• 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: 2-amino-3-(5-borono-1H-indol-3-yl)propanoic acid
• CAS: 1240784-16-0
• 化学式: C₁₁H₁₃BN₂O₄
• 分子量: 248.046
• InChiKey: VOHWFYJMEORABS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2-(diphenylmethyleneamino)-3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以95%的产率得到2-amino-3-(5-borono-1H-indol-3-yl)propanoic acid
  参考文献：
  名称：

  Direct, Regioselective, and Chemoselective Preparation of Novel Boronated Tryptophans by Friedel–Crafts Alkylation

  摘要：

  A facile synthetic approach to the direct preparation of various novel unnatural boronated protected tryptophans using a regio- and chemoselective electrophilic substitution of 4- and 5-boronated indoles with N-protected dehydroalanine is described. The gram-scale synthesis of two free tryptophan boronic acids is also reported.

  DOI：

  10.1021/ol203216h

文献信息

• Direct, Regioselective, and Chemoselective Preparation of Novel Boronated Tryptophans by Friedel–Crafts Alkylation
  作者：Silvia Bartolucci、Francesca Bartoccini、Marika Righi、Giovanni Piersanti

  DOI：10.1021/ol203216h

  日期：2012.1.20

  A facile synthetic approach to the direct preparation of various novel unnatural boronated protected tryptophans using a regio- and chemoselective electrophilic substitution of 4- and 5-boronated indoles with N-protected dehydroalanine is described. The gram-scale synthesis of two free tryptophan boronic acids is also reported.