trans-1-azido-1,2-dimethylcyclohexane | 144192-66-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: trans-1-azido-1,2-dimethylcyclohexane
• 英文别名: (1R,2S)-1-azido-1,2-dimethylcyclohexane
• CAS: 144192-66-5
• 化学式: C₈H₁₅N₃
• 分子量: 153.227
• InChiKey: WDXYKEFLPDFAIC-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-二甲基环己烯 在 三氟甲磺酸 叠氮基三甲基硅烷 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.2h， 以50%的产率得到trans-1-azido-1,2-dimethylcyclohexane
  参考文献：
  名称：

  Surface-mediated reactions. 2. Addition of hydrazoic acid to alkenes

  摘要：

  DOI：

  10.1021/jo00050a053

文献信息

• Manganese-Catalyzed Late-Stage Aliphatic C–H Azidation
  作者：Xiongyi Huang、Tova M. Bergsten、John T. Groves

  DOI：10.1021/jacs.5b01983

  日期：2015.4.29

  We report a manganese-catalyzed aliphatic azidation reaction that can, efficiently :Convert secondary, tertiary, and benzylic C-H bonds to the corresponding azides. The;method utilizes aqueous sodium azide solution as the azide source and can be performed under air. Besides its operational simplicity, the potential of this method for late-stage functionalization has been demonstrated by successful azidation of various, bioactive molecules, With yields up to 74%, including the important,drugs pregabalin, memantine, and the anti-malarial Azidation of celestolide with a chiral manganese salen catalyst afforded the azide product in 70% ee, representing a Mn-catalyzed enantioselective aliphatic C-H azidation reaction. Considering the versatile roles of organic aides in modem chemistry and the ubiquity of aliphatic C-H bond's in Organic molecules, We envision that this Mn-azidation method will find wide application in organic synthesis; drug discovery, and chemical biology.
• Surface-mediated reactions. 2. Addition of hydrazoic acid to alkenes
  作者：Gary W. Breton、Kimberlee A. Daus、Paul J. Kropp

  DOI：10.1021/jo00050a053

  日期：1992.11