3,9-diiodo-2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine

• 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-diiodo-2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine
• 英文别名: 4,12-Diiodo-5,13-dimethyl-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10(15),11,13-hexaene
• 化学式: C₁₇H₁₆I₂N₂
• 分子量: 502.136
• InChiKey: YHEBFLZSIXHVEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,4-二氨基甲苯 在 sodium nitrate 、 硫酸 、 氨 、 sodium iodide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 37.0h， 生成 3,9-diiodo-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

文献信息

• Synthesis of Dihalo-Substituted Analogues of Tröger’s Base from ortho- and meta-Substituted Anilines
  作者：Anna Hansson、Jacob Jensen、Ola F. Wendt、Kenneth Wärnmark

  DOI：10.1002/ejoc.200300144

  日期：2003.8

  dihalo-substituted analogues of Trogers base. By using paraformaldehyde and TFA, yields of 2-85% of these potential supramolecular building blocks were obtained. Even the inconceivable achievement of condensing anilines unsubstituted in para-position to analogues of Trogers base was successful. Adding our present results to our previous, makes it now possible to synthesize analogues of Trogers base halo-substituted

  首次将邻位和间位卤代苯胺与甲醛成功缩合成 Trogers 碱的二卤代类似物。通过使用多聚甲醛和 TFA，这些潜在超分子结构单元的产率为 2-85%。即使是将未取代的苯胺与 Trogers 碱的类似物缩合的不可思议的成就也是成功的。将我们目前的结果添加到我们之前的结果中，现在可以合成 Trogers 碱基的类似物，在其两个芳环中的每一个的几乎任何所需位置上都被卤代取代。此外，Trogers 碱的二卤取代类似物的第一个 X 射线结构，3,9-二溴-4,10-二甲基-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (17)，提出。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003) (Less)
• Hünlich Base: (Re)Discovery, Synthesis, and Structure Elucidation after a Century
  作者：Stephan Rigol、Lothar Beyer、Lothar Hennig、Joachim Sieler、Athanassios Giannis

  DOI：10.1021/ol400357t

  日期：2013.3.15

  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.