3,9-diazido-2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine | 1426400-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3,9-diazido-2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine
• CAS: 1426400-99-8
• 化学式: C₁₇H₁₆N₈
• 分子量: 332.368
• InChiKey: HFPDVZGXVQSRBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  104.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,9-diazido-2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine 、 苯乙炔 在 copper(l) iodide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以40%的产率得到3-azido-2,8-dimethyl-9-(4-phenyl-1H-1,2,3-triazol-1-yl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine
  参考文献：
  名称：

  Hünlich Base: (Re)Discovery, Synthesis, and Structure Elucidation after a Century

  摘要：

  After almost 100 years, the structure of the product of the reaction between 2,4-diaminotoluene and formaldehyde was elucidated: derivative 3, which we call the Hunlich base, was synthesized on a multigram scale and its enantiomers were easily separated in preparative amounts. Furthermore, transformation of the NH2 groups to the corresponding bis-iodides and bis-azides is presented. The latter was also used for desymmetrization by click chemistry.

  DOI：

  10.1021/ol400357t
• 作为产物：
  描述：

  2,4-二氨基甲苯 在 1H-咪唑-1-磺酰叠氮盐酸盐 、 硫酸 、 氨 、 potassium carbonate 、 copper(II) sulfate 作用下， 以 甲醇 、 水 为溶剂， 反应 54.0h， 生成 3,9-diazido-2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine
  参考文献：
  名称：

  Hünlich Base: (Re)Discovery, Synthesis, and Structure Elucidation after a Century

  摘要：

  After almost 100 years, the structure of the product of the reaction between 2,4-diaminotoluene and formaldehyde was elucidated: derivative 3, which we call the Hunlich base, was synthesized on a multigram scale and its enantiomers were easily separated in preparative amounts. Furthermore, transformation of the NH2 groups to the corresponding bis-iodides and bis-azides is presented. The latter was also used for desymmetrization by click chemistry.

  DOI：

  10.1021/ol400357t