2-amino-4,5-dihydro-1H-pyrrolo<3,2-h>quinoline-3-carboxylic acid ethyl ester | 137234-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-amino-4,5-dihydro-1H-pyrrolo<3,2-h>quinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 2-amino-4,5-dihydro-1H-pyrrolo[3,2-h]quinoline-3-carboxylate
• CAS: 137234-13-0
• 化学式: C₁₄H₁₅N₃O₂
• 分子量: 257.292
• InChiKey: YUBAORYFBGIQOG-UHFFFAOYSA-N

物化性质

• 沸点：
  570.7±50.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 3,3-diaminoacrylate 、 7-bromo-6,7-dihydro-8(5H)-quinolinone 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-amino-4,5-dihydro-1H-pyrrolo<3,2-h>quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Enolate complexation in acetonitrile with a neutral polyaza cleft

  摘要：

  DOI：

  10.1021/ja00025a052

文献信息

• Enolate complexation in acetonitrile with a neutral polyaza cleft
  作者：Anne M. Kelly-Rowley、Larry A. Cabell、Eric V. Anslyn

  DOI：10.1021/ja00025a052

  日期：1991.12
• Molecular Recognition of Enolates of Active Methylene Compounds in Acetonitrile. The Interplay between Complementarity and Basicity and the Use of Hydrogen Bonding to Lower Guest pKas
  作者：Anne M. Kelly-Rowley、Vincent M. Lynch、Eric V. Anslyn

  DOI：10.1021/ja00117a013

  日期：1995.3

  A model system for enolase and racemase enzymes was used to explore the extent to which traditional hydrogen bonds can increase carbon acidity. Polyazaclefts 1 and 2 were investigated as receptors for active methylene enolates 10 to 19 in acetonitrile. Receptor 1 was designed to form four hydrogen bonds to the heteroatoms of the enolate guests. The synthesis of the receptors began with the central pyridine ring followed by formation of the peripheral pyrrole rings. Binding constants for 1 with the enolates 10 to 17 in acetonitrile vary from 1.75 x 10(2) to 2.72 x 10(4) M(-1). The nature of both the enolate functionality and the counterion were found to affect the strength of complexation. Molecular mechanics and X-ray analysis of host 1 were used to predict the geometries of the guest-host complexes. Nonaqueous titrations with picric acid were performed on enolates 10 to 17 in order to assess the degree to which complexation was changed by the basicity of the enolate, Complementarity of the guest to host 1 was found to be the dominant factor in enolate binding and not guest basicity. However, a correlation was found to exist between basicity and binding for enolates of the same shape and functionality. Binding by host 1 was found to increase the acidity of 1,3-cyclohexanedione by 1.0 pK(a) unit in acetonitrile. Therefore, traditional hydrogen bonds exert only enough anion stabilization to account for a small fraction of the large pK(a) shifts found for enolase and racemase enzymes. Nevertheless, this acidity increase can be exploited as a means to induce deprotonation of 1,3-cyclohexanedione in the presence of 1.