ethyl N-(2-phenylethyl)indole-2-carboxylate | 108797-27-9

• 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: ethyl N-(2-phenylethyl)indole-2-carboxylate
• 英文别名: ethyl 1-phenethylindole-2-carboxylate；ethyl 1-(2-phenylethyl)indole-2-carboxylate
• CAS: 108797-27-9
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: IKFKHSOZMQSSEV-UHFFFAOYSA-N

物化性质

• 沸点：
  458.4±28.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl N-(2-phenylethyl)indole-2-carboxylate 在 三乙基硅烷 、 三甲基铝 作用下， 以 三氟乙酸 为溶剂， 反应 3.75h， 生成 2-(4,5-dihydro-1H-imidazol-2-yl)-1-(2-phenylethyl)-2,3-dihydroindole
  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：

  吲哚-2-羧酸乙酯 以19%的产率得到
  参考文献：
  名称：

  Abramovitch Rudolph A., Shi Qing, Bogdal Dariusz, Synth. Commun, 25 (1995) N 1, S 1-8

  摘要：

  DOI：

文献信息

• Thiazolidinedione derivatives, method for preparing the derivatives and
  申请人：Senga Pharmaceutical Laboratory Inc.

  公开号：US05811439A1

  公开（公告）日：1998-09-22

  A thiazolidinedione derivative represented by the following general formula (I): ##STR1## \x9bwherein the dotted line represents a single bond or a double bond, the thiazolidinedione ring residue is linked to either of 2-, 3-, 4-, 5- and 6-positions on the indole ring and R represents a group selected from the group consisting of hydrogen atom and alkyl, alkenyl, alkynyl, phenyl, aralkyl, heterocycloalkyl, arylsulfonyl and arylaminocarbonyl groups! or a pharmaceutically acceptable salt thereof exhibits excellent effects of reducing the blood sugar level and of reducing the lipid concentration in blood and is accordingly useful as a therapeutic agent for treating diabates mellitus. These derivatives and pharmaceutically acceptable salt thereof are almost free of any side effect.

  以下是通用公式（I）所代表的噻唑烷二酮衍生物：##STR1## 其中虚线代表单键或双键，噻唑烷二酮环残基连接到吲哚环的2-、3-、4-、5-和6-位置中的任一位置，R代表从氢原子和烷基、烯基、炔基、苯基、芳基烷基、杂环烷基、芳基磺酰基和芳基氨基甲酰基组成的群中选择的一个群！或其药学上可接受的盐表现出降低血糖水平和降低血液中脂质浓度的优异效果，因此可用作治疗糖尿病的治疗剂。这些衍生物及其药学上可接受的盐几乎没有任何副作用。
• Microwave-Assisted Alkylations of Activated Methylene Groups
  作者：Rudolph A. Abramovitch、Quing Shi、Dariusz Bogdal

  DOI：10.1080/00397919508010781

  日期：1995.1

  Abstract Alkylations under ‘dry conditions’ of nitrophenylacetates, of an indole, and of methyl benzylidene glycinate induced by microwaves have been studied, leading to a very simple synthesis of arenes linked by a long hydrocarbon chain. N-Alkylation of the indole occurs, and monoalkylated methyl benzylideneglycinate is obtained, but in poor yield.

  摘要 已经研究了在“干燥条件”下由微波诱导的硝基苯乙酸酯、吲哚和亚苄基甘氨酸甲酯的烷基化，从而可以非常简单地合成由长烃链连接的芳烃。吲哚发生N-烷基化反应，得到单烷基化的亚苄基甘氨酸甲酯，但收率很低。
• Thiazolidinedione derivatives, process for their preparation and pharmaceutical compositions containing them
  申请人：TOBISHI PHARMACEUTICAL CO., LTD.

  公开号：EP0780389A1

  公开（公告）日：1997-06-25

  A thiazolidinedione derivative represented by the following general formula (I): [wherein the dotted line represents a single bond or a double bond , the thiazolidinedione ring residue is linked to either of 2-, 3-, 4-, 5- and 6-positions on the indole ring and R represents a group selected from the group consisting of hydrogen atom and alkyl, alkenyl, alkynyl, phenyl, aralkyl, heterocycloalkyl, arylsulfonyl and arylaminocarbonyl groups] or a pharmaceutically acceptable salt thereof exhibits excellent effects of reducing the blood sugar level and of reducing the lipid concentration in blood and is accordingly useful as a therapeutic agent for treating diabates mellitus. These derivatives and pharmaceutically acceptable salt thereof are almost free of any side effect.

  由以下通式（I）代表的噻唑烷二酮衍生物： [其中虚线代表单键或双键，噻唑烷二酮环残基与吲哚环上的 2-、3-、4-、5-和 6-位中的任一个相连，R 代表选自氢原子和烷基、烯基、炔基、苯基、芳基、杂环烷基、芳基磺酰基和芳基氨基羰基组成的基团]或其药用盐、或其药学上可接受的盐具有极佳的降低血糖水平和血脂浓度的效果，因此可用作治疗糖尿病的药物。这些衍生物及其药学上可接受的盐几乎没有任何副作用。
• Abramovitch Rudolph A., Shi Qing, Bogdal Dariusz, Synth. Commun, 25 (1995) N 1, S 1-8
  作者：Abramovitch Rudolph A., Shi Qing, Bogdal Dariusz

  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：——