5,6,7,8-tetrahydro-4H-[1,2,3]triazolo[1,5-a]azepine | 1394843-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 5,6,7,8-tetrahydro-4H-[1,2,3]triazolo[1,5-a]azepine
• 英文别名: 5,6,7,8-tetrahydro-4H-triazolo[1,5-a]azepine
• CAS: 1394843-70-9
• 化学式: C₇H₁₁N₃
• 分子量: 137.184
• InChiKey: QNQQTCLRADKVJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  7-azidohept-1-yne 、 乙腈 在 gold(III) chloride 、 甲烷磺酸 作用下， 反应 10.0h， 以20%的产率得到3-methyl-6,7,8,9-tetrahydro-5H-imidazo[1,5-a]azepine
  参考文献：
  名称：

  Synthesis of Bicyclic Imidazoles via [2 + 3] Cycloaddition between Nitriles and Regioselectively Generated α-Imino Gold Carbene Intermediates

  摘要：

  The cyclic alpha-imino gold carbene intermediate B is most likely generated in situ via regioselective nitrene transfer from an azido group to a tethered terminal alkyne in the presence of a gold catalyst and at ambient temperature. This highly electrophilic intermediate can react with a weakly nucleophilic nitrile, which is used as the reaction solvent, to deliver a bicyclic imidazole rapidly in an overall bimolecular [2 + 2 + 1] cycloaddition and in mostly serviceable yield. The competing intramolecular Huisgen reaction, although likely also catalyzed by gold, is minimized by using AuCl3 as the catalyst.

  DOI：

  10.1021/ol302102h

文献信息

• INTRAMOLECULAR AZIDE-ALKYNE CYCLOADDITION
  申请人：Marcaurelle Lisa A.

  公开号：US20100280238A1

  公开（公告）日：2010-11-04

  The Huisgen 1,3-dipolar cycloaddition is a ‘click’ reaction that results from the ligation of azides and alkynes to give a triazole moiety. This reaction has been shown to be effective in the formation of a variety of macrocyclic rings. A key point of interest is the regioselectivity and specificity of the cycloaddition. Disclosed herein are specific, selective, and high-yielding methods of azide-alkyne macrocyclization to form 1,4- and 1,5-triazoles and libraries thereof.
• Synthesis of Bicyclic Imidazoles via [2 + 3] Cycloaddition between Nitriles and Regioselectively Generated α-Imino Gold Carbene Intermediates
  作者：Yuanjing Xiao、Liming Zhang

  DOI：10.1021/ol302102h

  日期：2012.9.7

  The cyclic alpha-imino gold carbene intermediate B is most likely generated in situ via regioselective nitrene transfer from an azido group to a tethered terminal alkyne in the presence of a gold catalyst and at ambient temperature. This highly electrophilic intermediate can react with a weakly nucleophilic nitrile, which is used as the reaction solvent, to deliver a bicyclic imidazole rapidly in an overall bimolecular [2 + 2 + 1] cycloaddition and in mostly serviceable yield. The competing intramolecular Huisgen reaction, although likely also catalyzed by gold, is minimized by using AuCl3 as the catalyst.