(1-benzyl-1H-1,2,3-triazol-4-yl)(piperidino)methanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1-benzyl-1H-1,2,3-triazol-4-yl)(piperidino)methanone
• 英文别名: (1-Benzyltriazol-4-yl)-piperidin-1-ylmethanone
• 化学式: C₁₅H₁₈N₄O
• 分子量: 270.334
• InChiKey: BNCXACXWYCRODE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(piperidin-1-yl)prop-2-yn-1-one 、 苄基叠氮 在 copper(II) sulfate sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以99%的产率得到(1-benzyl-1H-1,2,3-triazol-4-yl)(piperidino)methanone
  参考文献：
  名称：

  有效合成1,2,3-三唑的新型溶剂系统

  摘要：

  在有机叠氮化物和炔烃的铜（I）催化的1,3-偶极环加成反应中，使用CH 2 Cl 2与H 2 O的助溶剂可提高反应速率，并提供相应的1,2,3-三唑与其他有机助溶剂体系相比，产率极高。此外，我们利用这一发现以极好的收率制备了功能性多价化合物。

  DOI：

  10.1016/j.tetlet.2006.05.079

文献信息

• A convenient and efficient synthesis of C-carbamoyl-1,2,3-triazoles from alkyl bromide by a one-pot sequential addition: conversion of ester to amide using Zr(Ot-Bu)4
  作者：Dongsik Yang、Mihyun Kwon、Yujin Jang、Heung Bae Jeon

  DOI：10.1016/j.tetlet.2010.05.046

  日期：2010.7

  A convenient and efficient one-pot sequence has been developed for the synthesis of C-carbamoyl-1,2,3-triazoles from alkyl bromide using (i) sodium azide, (ii) methyl propiolate and copper iodide, and (iii) amines, zirconium tert-butoxide, and 1-hydroxybenzotriazole, under microwave irradiation. The sequential reactions in one-pot provided the desired C-carbamoyl-1,2,3-triazoles in excellent yields

  已经开发了一种方便有效的一锅法，用于使用（i）叠氮化钠，（ii）丙酸甲酯和碘化铜和（iii）胺从烷基溴合成C-氨基甲酰基-1,2,3-三唑，叔丁醇锆，1-羟基苯并三唑在微波辐射下。一锅中的顺序反应以优异的产率提供了所需的C-氨基甲酰基-1,2,3-三唑。
• A new solvent system for efficient synthesis of 1,2,3-triazoles
  作者：Bo-Young Lee、So Ra Park、Heung Bae Jeon、Kwan Soo Kim

  DOI：10.1016/j.tetlet.2006.05.079

  日期：2006.7

  The use of CH2Cl2 as a co-solvent with H2O in the copper(I)-catalyzed 1,3-dipolar cycloaddition of organic azides and alkynes increased reaction rates and provided the corresponding 1,2,3-triazoles in excellent yields compared to other organic co-solvent systems. Moreover, we applied this discovery to prepare the functional multivalent compound in an excellent yield.

  在有机叠氮化物和炔烃的铜（I）催化的1,3-偶极环加成反应中，使用CH 2 Cl 2与H 2 O的助溶剂可提高反应速率，并提供相应的1,2,3-三唑与其他有机助溶剂体系相比，产率极高。此外，我们利用这一发现以极好的收率制备了功能性多价化合物。
• Synthesis of <i>C</i>-Carbamoyl-1,2,3-triazoles by Microwave-Induced 1,3-Dipolar Cycloaddition of Organic Azides to Acetylenic Amides
  作者：Alan R. Katritzky、Sandeep K. Singh

  DOI：10.1021/jo026398u

  日期：2002.12.1

  1,3-Dipolar cycloaddition of organic azides 1, 2, or 3 to acetylenic amides 4 or 5 under solvent-free microwave irradiation produced the corresponding N-substituted C-carbamoyl-1,2,3-triazoles 7a-12a in good to excellent yields. Under similar reaction conditions, 1,3-dipolar cycloaddition of diazide 6 and acetylenic amide 4 gave the azido-triazole 13a.
• Unusual Cu(I)-catalyzed 1,3-dipolar cycloaddition of acetylenic amides: formation of bistriazoles
  作者：Mihyun Kwon、Yujin Jang、Sunyoung Yoon、Dongsik Yang、Heung Bae Jeon

  DOI：10.1016/j.tetlet.2012.01.069

  日期：2012.3

  C-carbamoyl-1,2,3-triazoles have recently attracted much interest due to their potent biological activity. While synthesizing C-carbamoyl-1,2,3-triazoles by the copper(l)-catalyzed 1,3-dipolar cycloaddition of organic azides 1 and acetylenic amides 2, we found that the expected 1,2,3-triazole products 3 were obtained as the only products in excellent yields when CuSO4 and sodium ascorbate were used as the Cu(I)-catalyst. Surprisingly, the unexpected bistriazole products 4 were one of the major products obtained along with the 1,2,3-triazoles 3 when using a direct Cu(I)-catalyst such as CuI or CuBr. (C) 2012 Elsevier Ltd. All rights reserved.