methyl 3-(1H-indol-1-yl)-2-methylpropanoate | 221687-62-3

• 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: methyl 3-(1H-indol-1-yl)-2-methylpropanoate
• CAS: 221687-62-3
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: GMRZSTOQFIPMHC-UHFFFAOYSA-N

物化性质

• 沸点：
  347.9±25.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 3-(1H-indol-1-yl)-2-methylpropanoate 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 12.0h， 生成 1-吲哚丙酸
  参考文献：
  名称：

  Computational and Experimental Studies of (2,2)-Bis(indol-1-yl-methyl)acetate Suggest the Importance of the Hydrophobic Effect in Aromatic Stacking Interactions

  摘要：

  To understand the driving forces of aromatic stacking interactions in water, we have performed conformational searches, molecular dynamics simulations, potential of mean force (PMF) and free energy perturbation (FEP) calculations, syntheses, and NMR studies on sodium (2,2)-bis(indol-1-yl-methyl)acetate (1), sodium 3-indol-1-yl-2-methyl-propionate (2), and sodium 3-indol-1-yl-propionate (3). The conformational searches on 1 revealed that the isobutyric acid linker of 1 allows the molecule to adopt the tilted T-shaped stacked, off-center stacked, face-to-face stacked, and nonstacked conformations in a vacuum. The PMF and FEP calculations suggested that the most thermodynamically stable conformers in water are the tilted T-shaped stacked and nonstacked conformers. Independent NMR spectroscopic studies of 1-3 revealed that both the tilted T-shaped stacked and nonstacked conformers are populated in D2O and in d(6)-DMSO, and they are: in a rapid equilibrium. Furthermore, the NMR studies found (i) a larger population of the tilted T-shaped stacked conformation of 1 at 22 degrees C in D2O than in d(6)-DMSO and (ii) more different populated stacked conformations of 1 at 60 degrees C in D2O than in d(6)-DMSO. One would expect larger populations of the stacked conformations in d(6)-DMSO, whose dielectric constant is smaller than that of water, if the electrostatic interaction were the only driving force of the aromatic stacking interactions. The results, therefore, suggest that the hydrophobic effect plays an important role in the stacking interaction of 1 in water.

  DOI：

  10.1021/ja9828410
• 作为产物：
  描述：

  吲哚 、 甲基丙烯酸甲酯 在 二甲基亚砜 、 potassium hydroxide 作用下， 反应 20.0h， 以74%的产率得到methyl 3-(1H-indol-1-yl)-2-methylpropanoate
  参考文献：
  名称：

  通过加氢胺化的烯烃定向合成线性和支化N-烷基化杂环

  摘要：

  描述了N-杂环与烯烃的选择性碱介导加氢胺化反应，用于构建直链和支链N-烷基化杂环。该协议提供了专有的N-烷基化产物而不是C-3 Michael加成产物的合成。

  DOI：

  10.1002/ejoc.202000373