ethyl-2,3-dihydro-1-phenylindole-2-carboxylate | 108797-70-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl-2,3-dihydro-1-phenylindole-2-carboxylate
• 英文别名: ethyl 1-phenyl-2,3-dihydroindole-2-carboxylate
• CAS: 108797-70-2
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: IPWSIZPDZBTRBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙二胺 、 ethyl-2,3-dihydro-1-phenylindole-2-carboxylate 在 三甲基铝 作用下， 生成 2-(4,5-Dihydro-1H-imidazol-2-yl)-1-phenyl-2,3-dihydro-1H-indole
  参考文献：
  名称：

  .alpha.2-Adrenergic agonists/antagonists: the synthesis and structure-activity relationships of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines

  摘要：

  The synthesis and alpha 2-adrenergic activity of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines are described. The indolin-2-yl imidazoline 4b was found to possess potent alpha 2-adrenergic agonist and antagonist activity. The modification of the substituents on the indoline ring of 4b has led to the separation of these activities. Substitution on the aromatic ring of 4b with halogen or increasing the size of the N-alkyl substituent of 4b gave alpha 2-adrenergic antagonists without agonist activity. The N-allylindoline 4d is more potent than idazoxan in vitro and is equipotent in vivo, but is less receptor selective (alpha 2 vs. alpha 1) than idazoxan. The cis-1,3-dimethylindolin-2-yl imidazoline 6a is an alpha 2-adrenergic agonist equal in potency to clonidine in vitro, while the trans-1,3-dimethylindolin-2-yl imidazoline 6b is a moderately potent alpha 2-adrenergic antagonist.

  DOI：

  10.1021/jm00392a005
• 作为产物：
  描述：

  在 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以95%的产率得到ethyl-2,3-dihydro-1-phenylindole-2-carboxylate
  参考文献：
  名称：

  Synthesis of Indolines by a Zn-Mediated Mannich Reaction/Pd-Catalyzed Amination Sequence

  摘要：

  1,2-Disubstituted indolines have been prepared in fair to good yields by a Zn-mediated organometallic Mannich reaction, followed by an intramolecular Pd-catalyzed aromatic amination. The reactions are easy to set up and compatible with a large variety of simple or commercially available reagents. The method was further extended to the preparation of a 1,2,3-trisubstituted indoline.

  DOI：

  10.1021/acs.joc.7b00013

文献信息

• 2,3-dihydro-2-(4,5-dihydroimidazol-2-yl)-indoles in composition form for
  申请人：Ciba-Geigy Corporation

  公开号：US04908376A1

  公开（公告）日：1990-03-13

  Compounds of the formula ##STR1## wherein each R is hydrogen or one R is hydrogen and the other is lower alkyl, R.sub.1 is hydrogen, lower alkyl, aryl, aralkyl or lower carboalkoxy, R.sub.2 is hydrogen or lower alkyl, and the ring A is unsubstituted or substituted by lower alkyl, lower alkoxy, halo or trifluoromethyl, and pharmaceutically acceptable salts thereof, their preparation, pharmaceutical compositions and the uses thereof, such as .alpha..sub.2 -adrenergic blocking agents, e.g. antidepressants, cognition enhancers and appetite suppressants, and as intraocular pressure reducing agents are disclosed.

  式为##STR1##的化合物，其中每个R是氢或一个R是氢而另一个是较低的烷基，R.sub.1是氢，较低的烷基，芳基，芳基烷基或较低的羰基烷氧基，R.sub.2是氢或较低的烷基，环A未取代或被较低的烷基，较低的烷氧基，卤素或三氟甲基取代，以及其药学上可接受的盐，其制备，药物组合物及其用途，例如α2-肾上腺素受体阻滞剂，如抗抑郁药，认知增强剂和食欲抑制剂，以及作为降低眼压的药剂。
• 2,3-dihydro-2-(4,5-dihydroimidazol-2-yl)-indoles for reducing
  申请人：Ciba-Geigy Corporation

  公开号：US04912125A1

  公开（公告）日：1990-03-27

  Compounds of the formula ##STR1## wherein each R is hydrogen or one R is hydrogen and the other is lower alkyl, R.sub.1 is hydrogen, lower alkyl, aryl, aralkyl or lower carboalkoxy, R.sub.2 is hydrogen or lower alkyl, and the ring A is unsubstituted or substituted by lower alkyl, lower alkoxy, halo or trifluoromethyl, and pharmaceutically acceptable salts thereof, their preparation, pharmaceutical compositions and the uses thereof, such as .alpha..sub.2 -adrenergic blocking agents, e.g. antidepressants, cognition enhancers and appetite supressants, and as intraocular pressure reducing agents are disclosed.

  本发明公开了化学式为##STR1##的化合物，其中每个R是氢或一个R是氢，另一个是较低的烷基，R.sub.1是氢，较低的烷基，芳基，芳基烷基或较低的羧基烷氧基，R.sub.2是氢或较低的烷基，环A未经取代或被较低的烷基，较低的烷氧基，卤素或三氟甲基取代，以及其药学上可接受的盐，其制备，制药组合物和用途，例如作为α2-肾上腺素能阻断剂，例如抗抑郁剂，认知增强剂和食欲抑制剂，以及作为降低眼内压的剂。
• .alpha.2-Adrenergic agonists/antagonists: the synthesis and structure-activity relationships of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines
  作者：Dennis J. Hlasta、Daniel Luttinger、Mark H. Perrone、Marla J. Silbernagel、Susan J. Ward、Dean R. Haubrich

  DOI：10.1021/jm00392a005

  日期：1987.9

  The synthesis and alpha 2-adrenergic activity of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines are described. The indolin-2-yl imidazoline 4b was found to possess potent alpha 2-adrenergic agonist and antagonist activity. The modification of the substituents on the indoline ring of 4b has led to the separation of these activities. Substitution on the aromatic ring of 4b with halogen or increasing the size of the N-alkyl substituent of 4b gave alpha 2-adrenergic antagonists without agonist activity. The N-allylindoline 4d is more potent than idazoxan in vitro and is equipotent in vivo, but is less receptor selective (alpha 2 vs. alpha 1) than idazoxan. The cis-1,3-dimethylindolin-2-yl imidazoline 6a is an alpha 2-adrenergic agonist equal in potency to clonidine in vitro, while the trans-1,3-dimethylindolin-2-yl imidazoline 6b is a moderately potent alpha 2-adrenergic antagonist.
• HUEBNER, CHARLES F.;FRANCIS, JOHN E.
  作者：HUEBNER, CHARLES F.、FRANCIS, JOHN E.

  DOI：——

  日期：——
• HLASTA, DENNIS J.;LUTTINGER, DANIEL;PERRONE, MARK H.;SILBERNAGEL, MARLA J+, J. MED. CHEM., 30,(1987) N 9, 1555-1562
  作者：HLASTA, DENNIS J.、LUTTINGER, DANIEL、PERRONE, MARK H.、SILBERNAGEL, MARLA J+

  DOI：——

  日期：——