3-Oxa-10,16,17,18-tetrazatricyclo[14.2.1.04,9]nonadeca-1(19),4,6,8,17-pentaen-11-one | 1158174-91-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 3-Oxa-10,16,17,18-tetrazatricyclo[14.2.1.04,9]nonadeca-1(19),4,6,8,17-pentaen-11-one
• CAS: 1158174-91-4
• 化学式: C₁₄H₁₆N₄O₂
• 分子量: 272.307
• InChiKey: MAGWSWVWDNMABY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-azido-N-(2-prop-2-ynoxyphenyl)pentanamide 在 Amberlyst-21-supported CuPF₆ 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以31%的产率得到3-Oxa-10,16,17,18-tetrazatricyclo[14.2.1.04,9]nonadeca-1(19),4,6,8,17-pentaen-11-one
  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

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

  公开号：WO2010127088A2

  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.