3-(cyanomethyl)-2-ethyl-1-(phenylmethyl)-5-methoxyindole | 184705-14-4

• 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: 3-(cyanomethyl)-2-ethyl-1-(phenylmethyl)-5-methoxyindole
• 英文别名: 1-benzyl-3-cyanomethyl-2-ethyl-5-methoxyindole；2-(1-Benzyl-2-ethyl-5-methoxyindol-3-yl)acetonitrile
• CAS: 184705-14-4
• 化学式: C₂₀H₂₀N₂O
• 分子量: 304.392
• InChiKey: RUPCPRBZJWYLSU-UHFFFAOYSA-N

物化性质

• 沸点：
  511.9±50.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(cyanomethyl)-2-ethyl-1-(phenylmethyl)-5-methoxyindole 在 氢氧化钾 、 四丁基溴化铵 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 20.5h， 生成 2-[1-Benzyl-5-[3-bis(trimethylsilyloxy)phosphorylpropoxy]-2-ethylindol-3-yl]acetamide
  参考文献：
  名称：

  A Practical, Nenitzescu-Based Synthesis of LY311727, the First Potent and Selective s-PLA₂ Inhibitor

  摘要：

  DOI：

  10.1021/jo9614452
• 作为产物：
  描述：

  3-氧代戊酸甲酯 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 四丁基溴化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 硝基甲烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 53.5h， 生成 3-(cyanomethyl)-2-ethyl-1-(phenylmethyl)-5-methoxyindole
  参考文献：
  名称：

  A Practical, Nenitzescu-Based Synthesis of LY311727, the First Potent and Selective s-PLA₂ Inhibitor

  摘要：

  DOI：

  10.1021/jo9614452

文献信息

• Isoharmine Revisited: Thermal Rearrangement of a 3-Cyanomethyl-2-vinylindole
  作者：Janos Sapi、Dominique Patigny、Jean-Yves Laronze

  DOI：10.3987/com-98-8399

  日期：——

  Thermolysis of 2-vinylindole derivative (1) led to indolylacrylonitrile (6) instead of beta-carboline alkaloid isoharmine (4). Latter was prepared by following the conventional method and was fully characterized.
• [EN] N-BENZYLINDOLE-3-ACETIC ACID DERIVATIVES FOR USE IN THE TREATMENT OF DRUG RESISTAN CANCER<br/>[FR] DERIVES D'ACIDE ACETIQUE N-BENZYLINDOLE-3 POUVANT ETRE UTILISES DANS LE TRAITEMENT DE CANCERS PHARMACORESISTANTS
  申请人：UNIV DUBLIN CITY

  公开号：WO2002020478A1

  公开（公告）日：2002-03-14

  A family of compounds, N-Benzylindoel-3-acetic acid derivatives, are active as inhibitors of multiple drug resistance protein (MRP) while having low direct toxicity, low COX -1 inhibitory activity and, in some cases, having useful activities such as COX-1 inhibition. The agents are useful in combination with MRP substrate drugs in the treatment of, for example, drug resistant cancer or tumours likely to develop drug resistant cancers because they can be given at higher concentration while being less toxic and having less side effects than known MRP inhibitors. The agents may also be more beneficial in the treatment of diseases which are dependent on MRP-1 activity or where MRP-1 activity reduces the effectiveness of existing therapies.
• Synthesis of indomethacin analogues for evaluation as modulators of MRP activity
  作者：Anita R. Maguire、Stephen J. Plunkett、Sébastien Papot、Martin Clynes、Robert O'Connor、Samantha Touhey

  DOI：10.1016/s0968-0896(00)00292-3

  日期：2001.3

  Synthesis of a range of indomethacin analogues, required for investigation in combination toxicity assays, bearing both N-benzyl and N-benzoyl groups, is described. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A Practical, Nenitzescu-Based Synthesis of LY311727, the First Potent and Selective s-PLA₂ Inhibitor
  作者：J. M. Pawlak、V. V. Khau、D. R. Hutchison、M. J. Martinelli

  DOI：10.1021/jo9614452

  日期：1996.1.1