ethyl 2-ethyl-2,3-dihydro-1-methyl-1H-indole-2-carboxylate | 113162-35-9

• 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: ethyl 2-ethyl-2,3-dihydro-1-methyl-1H-indole-2-carboxylate
• 英文别名: ethyl 2-ethyl-1-methyl-3H-indole-2-carboxylate
• CAS: 113162-35-9
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: YHYYFQVFROGKFT-UHFFFAOYSA-N

物化性质

• 沸点：
  325.3±30.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  乙二胺 、 ethyl 2-ethyl-2,3-dihydro-1-methyl-1H-indole-2-carboxylate 在 三甲基铝 作用下， 以 甲苯 为溶剂， 以17.5%的产率得到2-(4,5-dihydro-2-1H-imidazolyl)-2-ethyl-2,3-dihydro-1-methyl-1H-indole
  参考文献：
  名称：

  Indoline analogs of idazoxan: potent .alpha.2-antagonists and .alpha.1-agonists

  摘要：

  The synthesis and alpha-adrenergic activity of a series of substituted 2-imidazolinylindolines are described. Substitution in the indoline ring generated compounds with a spectrum of adrenoceptor antagonist/agonist profiles that proved sensitive to both the nature and position of the substituent. Many of the derivatives possess greater presynaptic antagonist potency than the corresponding benzodioxan 1, dihydrobenzofuran 2, and indan 3 analogues; however, this alpha 2-antagonism is often accompanied by alpha 1-agonist activity. It was not possible to separate alpha 2-antagonist from alpha 1-agonist properties in this series. Compounds of most interest proved to be the N-ethyl 6, 5-chloro-N-methyl 18, and 5-chloro-N-ethyl 23 derivatives, all being potent alpha 2-antagonists and alpha 1-agonists. Substitution at the 4- and 7-position of the indoline ring generally gave compounds with nonselective agonist properties.

  DOI：

  10.1021/jm00400a009
• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 在 potassium sulfate 、 sodium cyanoborohydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 三氟乙酸 为溶剂， 反应 4.0h， 生成 ethyl 2-ethyl-2,3-dihydro-1-methyl-1H-indole-2-carboxylate
  参考文献：
  名称：

  Indoline analogs of idazoxan: potent .alpha.2-antagonists and .alpha.1-agonists

  摘要：

  The synthesis and alpha-adrenergic activity of a series of substituted 2-imidazolinylindolines are described. Substitution in the indoline ring generated compounds with a spectrum of adrenoceptor antagonist/agonist profiles that proved sensitive to both the nature and position of the substituent. Many of the derivatives possess greater presynaptic antagonist potency than the corresponding benzodioxan 1, dihydrobenzofuran 2, and indan 3 analogues; however, this alpha 2-antagonism is often accompanied by alpha 1-agonist activity. It was not possible to separate alpha 2-antagonist from alpha 1-agonist properties in this series. Compounds of most interest proved to be the N-ethyl 6, 5-chloro-N-methyl 18, and 5-chloro-N-ethyl 23 derivatives, all being potent alpha 2-antagonists and alpha 1-agonists. Substitution at the 4- and 7-position of the indoline ring generally gave compounds with nonselective agonist properties.

  DOI：

  10.1021/jm00400a009

文献信息

• FAGAN, GAY P.;CHAPLEO, CHRISTOPHER B.;LANE, ANTHONY C.;MYERS, MALCOLM;ROA+, J. MED. CHEM., 31,(1988) N 5, 944-948
  作者：FAGAN, GAY P.、CHAPLEO, CHRISTOPHER B.、LANE, ANTHONY C.、MYERS, MALCOLM、ROA+

  DOI：——

  日期：——