1-(piperidin-1-ylmethyl)-1H-indole | 5379-84-0

• 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-(piperidin-1-ylmethyl)-1H-indole
• 英文别名: 1-piperidin-1-ylmethyl-indole；3-(N-piperidinomethyl)indole；1-(piperidin-1-ylmethyl)indole
• CAS: 5379-84-0
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: TZKKDRZGWAEGHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  哌啶 在 三氟甲磺酸三甲基硅酯 、 potassium carbonate 、 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-(piperidin-1-ylmethyl)-1H-indole 、 3-((哌啶-1-基)甲基)-1H-吲哚
  参考文献：
  名称：

  N-Aminomethylation vs. C-Aminomethylation of Indole and Pyrrole with an N,O-Acetal Controlled by the Hardness of a Counter Ion of an Iminium Compound

  摘要：

  在使用 TMSOTf 和 TMSI 的相对较强的路易斯酸条件下（较软的反离子），吲哚或吡咯与典型的 N,O-缩醛的氨基甲基化反应优先产生动力学上有利的 N-氨基甲基化吲哚或吡咯衍生物。使用相对较弱的路易斯酸（较硬的反离子），如 TMSCl 和 TMSBr，优先产生热力学上有利的 C-氨基甲基化吲哚和吡咯衍生物。

  DOI：

  10.1246/cl.131116

文献信息

• A General Synthesis of 1-(Dialkylaminomethyl)indoles
  作者：Brian E. Love、Binh T. Nguyen

  DOI：10.1055/s-1998-1883

  日期：1998.10

  1-(N,N-Dialkylamino)methylindoles are prepared from the corresponding 1-(dialkylaminomethyl)benzotriazoles by treatment with indole and base. The aminoalkylation proceeds in high yield with good regioselectivity.

  1-(N,N-二烷基氨基)甲基吲哚是通过用吲哚和碱处理相应的1-(二烷基氨基甲基)苯并三唑制备的。氨基烷基化反应在高产率和良好区域选择性的条件下进行。
• Mannich Base N-Oxide Drugs
  申请人：Keana John F.W.

  公开号：US20100016252A1

  公开（公告）日：2010-01-21

  Disclosed are Mannich base N-oxides of drugs containing acidic N—H groups. Pharmaceutical compositions comprising a therapeutically effective amount of Mannich base N-oxides, or a N-oxide rearrangement product, pharmaceutically acceptable salt or prodrug thereof, are also disclosed. Further, disclosed are methods of using the compounds, alone or in combination with one or more other active agents or treatments.

  本发明涉及含有酸性N-H基团的药物的Mannich碱N-氧化物。还公开了包含治疗有效量的Mannich碱N-氧化物、氧化物重排产物、药学上可接受的盐或前药的制药组合物。此外，还公开了使用该化合物的方法，单独或与一种或多种其他活性剂或治疗方法结合使用。
• Hf(OTf)₄-Catalyzed Regioselective <i>N</i>-Aminomethylation of Indoles and Related NH-Containing Heterocycles
  作者：Norio Sakai、Kazuyori Shimamura、Reiko Ikeda、Takeo Konakahara

  DOI：10.1021/jo1006043

  日期：2010.6.4

  Under Lewis acidic conditions using Hf(OTf)(4), the aminomethylation of an indole derivative with a typical N,O-acetal preferentially produced kinetically favored N-aminomethylated indole derivatives instead of thermodynamically favored 3-aminomethylated indoles.
• Indium trichloride catalyzed three component one-pot route to 1-hydroxymethyl-3-aminomethyl indoles
  作者：Chiranjit Acharya、Sumit Dey、Parasuraman Jaisankar

  DOI：10.1016/j.tetlet.2012.08.034

  日期：2012.10

  A one-pot synthesis of 1-hydroxymethyl-3-aminomethyl indoles 3 could be achieved in excellent yield by reacting indoles 1 with formaldehyde and secondary amines 2 in the presence of molecular sieves (3 angstrom) and catalytic amount of InCl3 (10 mol %) in 1,4-dioxane at room temperature for 3-5 h. (C) 2012 Elsevier Ltd. All rights reserved.
• Potentiation of MC4 receptor activity
  申请人：Bennett A. Teresa

  公开号：US20080027072A1

  公开（公告）日：2008-01-31

  The present invention provides methods of treating obesity, eating disorders, and sexual dysfunction. The methods comprise administering to a mammalian host suffering from obesity, an eating disorder, or sexual dysfunction an effective dose of a compound of the invention. Also provided are methods of potentiating the effect of an MC4 receptor agonist in a mammalian host. In some cases the methods comprise administering to the host a compound that lowers the EC 50 of the agonist. In other cases the methods comprise administering to the host a compound that increases the maximum effect of the agonist.