4-azido-N-(2-hydroxyethyl)-N-methylbutanamide | 1158174-54-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-azido-N-(2-hydroxyethyl)-N-methylbutanamide
• CAS: 1158174-54-9
• 化学式: C₇H₁₄N₄O₂
• 分子量: 186.214
• InChiKey: VNGMDPANXAWNGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-azido-N-(2-hydroxyethyl)-N-methylbutanamide 、 3-溴丙炔 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以83%的产率得到4-azido-N-methyl-N-(2-(prop-2-ynyloxy)ethyl)butanamide
  参考文献：
  名称：

  Accessing Skeletal Diversity Using Catalyst Control: Formation of n and n + 1 Macrocyclic Triazole Rings

  摘要：

  A regloselective intramolecular Huisgen cycloaddition was performed on various azido alkyne substrates giving rise to macrocyclic triazole rings. Using catalyst control, a common intermediate has been converted to two structurally unique macrocycles with either a 1,5- or a 1,4-triazole resulting in an n or n + 1 ring size. This is the first example of an intramolecular ruthenium-catalyzed Huisgen cycloaddition.

  DOI：

  10.1021/ol900562u
• 作为产物：
  描述：

  4-azido-N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-methylbutanamide 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 以66%的产率得到4-azido-N-(2-hydroxyethyl)-N-methylbutanamide
  参考文献：
  名称：

  [EN] INTRAMOLECULAR AZIDE-ALKYNE CYCLOADDITION
  [FR] CYCLO-ADDITION AZIDE-ALCYNE INTRAMOLÉCULAIRE

  摘要：

  公开号：

  WO2010127088A3

文献信息

• [EN] INTRAMOLECULAR AZIDE-ALKYNE CYCLOADDITION<br/>[FR] CYCLO-ADDITION AZIDE-ALCYNE INTRAMOLÉCULAIRE
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2010127088A3

  公开（公告）日：2011-03-31
• 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.
• Accessing Skeletal Diversity Using Catalyst Control: Formation of <i>n</i> and <i>n</i> + 1 Macrocyclic Triazole Rings
  作者：Ann Rowley Kelly、Jingqiang Wei、Sarathy Kesavan、Jean-Charles Marié、Nicole Windmon、Damian W. Young、Lisa A. Marcaurelle

  DOI：10.1021/ol900562u

  日期：2009.6.4

  A regloselective intramolecular Huisgen cycloaddition was performed on various azido alkyne substrates giving rise to macrocyclic triazole rings. Using catalyst control, a common intermediate has been converted to two structurally unique macrocycles with either a 1,5- or a 1,4-triazole resulting in an n or n + 1 ring size. This is the first example of an intramolecular ruthenium-catalyzed Huisgen cycloaddition.