1-(4,5-Dihydro-1H-imidazol-2-yl)-1H-indole-3-carboxylic acid ethyl ester | 180520-68-7

• 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: 1-(4,5-Dihydro-1H-imidazol-2-yl)-1H-indole-3-carboxylic acid ethyl ester
• 英文别名: ethyl 1-(4,5-dihydro-1H-imidazol-2-yl)indole-3-carboxylate
• CAS: 180520-68-7
• 化学式: C₁₄H₁₅N₃O₂
• 分子量: 257.292
• InChiKey: OCDCBASWGBNTNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-(4,5-Dihydro-1H-imidazol-2-yl)-1H-indole-3-carboxylic acid ethyl ester 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以54%的产率得到1-(1-Acetyl-4,5-dihydro-1H-imidazol-2-yl)-1H-indole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis, structure and antiaggregatory effects of some N-(4,5-dihydro-1H-imidazol-2-yl)indoles

  摘要：

  A series of 1-(4,5-dihydro-1H-imidazol-2-yl)indole derivatives was prepared in order to evaluate their antiaggregatory activity in human platelets. The compounds 4a-m were prepared by reacting N-aryl-N-(4,5-dihydro-1H-imidazol-2-yl)hydroxylamines (2a-d) with monosubstituted acetylene derivatives 3a-b. Imidazoline derivatives 4 were further acetylated or sulfonylated to give amides 5a-c and sulfonamides 6a-c and 7a-c, respectively. Eight compounds were taken as representative aryliminoimidazoline analogs. Among them only one, 4m, showed a good concentration-dependent action against the primary or alpha(2)-adrenoreceptor mediated phase of noradrenaline-induced aggregation in platelets. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00123-8
• 作为产物：
  描述：

  N-(4,5-dihydro-1H-imidazol-2-yl)-N-phenylhydroxylamine hydrochloride 、 丙炔酸乙酯 在 三乙胺 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以65%的产率得到1-(4,5-Dihydro-1H-imidazol-2-yl)-1H-indole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis, structure and antiaggregatory effects of some N-(4,5-dihydro-1H-imidazol-2-yl)indoles

  摘要：

  A series of 1-(4,5-dihydro-1H-imidazol-2-yl)indole derivatives was prepared in order to evaluate their antiaggregatory activity in human platelets. The compounds 4a-m were prepared by reacting N-aryl-N-(4,5-dihydro-1H-imidazol-2-yl)hydroxylamines (2a-d) with monosubstituted acetylene derivatives 3a-b. Imidazoline derivatives 4 were further acetylated or sulfonylated to give amides 5a-c and sulfonamides 6a-c and 7a-c, respectively. Eight compounds were taken as representative aryliminoimidazoline analogs. Among them only one, 4m, showed a good concentration-dependent action against the primary or alpha(2)-adrenoreceptor mediated phase of noradrenaline-induced aggregation in platelets. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00123-8

文献信息

• Reactions of <i>N</i>-Aryl-<i>N</i>-(4,5-dihydro-1<i>H</i>-imidazol-2-yl)hydroxylamines with Electron-Deficient Acetylenes. Synthesis and Structure of Novel Heterocyclic Ketene Aminals
  作者：Franciszek Saczewski、Tomasz Debowski、Maria Gdaniec、Zofia Gdaniec

  DOI：10.1021/jo960319v

  日期：1996.1.1

  Reactions of the title hydroxylamine hydrochlorides 1 with electron-deficient acetylenes 3 are described. Compounds la reacts with ethyl propiolate (3a) to give the expect-ed indole 7, Similar reactions of la-e with disubstituted acetylene derivatives such as diethyl acetylenedicarboxylate (3b), dimethyl acetylenedicarboxylate (3c), or ethyl phenylpropiolate (3d) lead to the formation of novel heterocyclic ketene aminals 9a-m. X-ray crystal structure and NMR spectra of 9a are described in detail.