(+/-)-2-iodo-6H,12H,5,11-methanodibenzo[b,f][1,5]diazocine | 951760-12-6

• 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: (+/-)-2-iodo-6H,12H,5,11-methanodibenzo[b,f][1,5]diazocine
• 英文别名: 5-Iodo-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10,12,14-hexaene
• CAS: 951760-12-6
• 化学式: C₁₅H₁₃IN₂
• 分子量: 348.186
• InChiKey: HPHBOOUPYQWYTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-2-iodo-6H,12H,5,11-methanodibenzo[b,f][1,5]diazocine 在 sodium carbonate 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 120.0h， 生成 (-)-R,R-2-iodo-6,12-dihydro-5,11-methanodibenzo[b,f ][1,5]-diazocine
  参考文献：
  名称：

  Application of Crystallization-Induced Asymmetric Transformation to a General, Scalable Method for the Resolution of 2,8-Disubstituted Tröger’s Base Derivatives

  摘要：

  A general method for the gram scale resolution of 2-substituted and 2,8-disubstituted Troger's base (TB) derivatives in 63-91% yield has been achieved through the application of crystallization-induced asymmetric transformation (CIAT). Enantiomeric ratios of the resolved TB derivatives range from 99.1:0.9 to >99.5:0.5. Among the Troger's base compounds resolved are four synthetically valuable bromo and iodo derivatives.

  DOI：

  10.1021/jo401873x
• 作为产物：
  描述：

  (+)-S,S-2-iodo-6,12-dihydro-5,11-methanodibenzo[b,f ][1,5]-diazocine*(+)-O,O′-dibenzoyl-D-tartaric acid 在 sodium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 以96%的产率得到(+/-)-2-iodo-6H,12H,5,11-methanodibenzo[b,f][1,5]diazocine
  参考文献：
  名称：

  Application of Crystallization-Induced Asymmetric Transformation to a General, Scalable Method for the Resolution of 2,8-Disubstituted Tröger’s Base Derivatives

  摘要：

  A general method for the gram scale resolution of 2-substituted and 2,8-disubstituted Troger's base (TB) derivatives in 63-91% yield has been achieved through the application of crystallization-induced asymmetric transformation (CIAT). Enantiomeric ratios of the resolved TB derivatives range from 99.1:0.9 to >99.5:0.5. Among the Troger's base compounds resolved are four synthetically valuable bromo and iodo derivatives.

  DOI：

  10.1021/jo401873x

文献信息

• Bromination and Iodination of 6H,12H-5,11-Methanodibenzo[b,f][1,5]diazocine: A Convenient Entry to Unsymmetrical Analogs of Tröger's Base
  作者：Delphine Didier、Sergey Sergeyev

  DOI：10.1002/ejoc.200700253

  日期：2007.8

  11-Methanodibenzo[b,f][1,5]diazocine can easily be prepared from aniline and paraformaldehyde. Its reactions with either N-bromosuccinimide (NBS) or with iodine monochloride (ICl) in the presence of a suitable activator smoothly afford 2-bromo- and 2-iodo- derivatives, respectively. The combination of these halogenation methods provides access to the 8-bromo-2-iodo derivative, which is an interesting and otherwise

  6H,12H-5,11-Methanodibenzo[b,f][1,5]diazocine 可以很容易地从苯胺和多聚甲醛制备。在合适的活化剂存在下，它与 N-溴代琥珀酰亚胺 (NBS) 或与一氯化碘 (ICl) 的反应分别顺利地得到 2-溴-和 2-碘-衍生物。这些卤化方法的组合提供了获得 8-bromo-2-iodo 衍生物的途径，这是一种有趣的中间体，用于合成 Troger 碱的不对称类似物。报道的卤化代表了 6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine 亲电取代的第一个例子。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• One-Step Synthesis of Tröger's Base Hybrids Containing at Least One Halogen Atom
  作者：Masoud Faroughi、Kai-Xian Zhu、Paul Jensen、Donald C. Craig、Andrew C. Try

  DOI：10.1002/ejoc.200900121

  日期：2009.9

  The one-step synthesis of a series of hybrid dibenzo Troger's base analogues bearing at least one halogen atom is described. The strategy involves a reaction between two different anilines and affords hybrid compounds in yields as high as 46 %, together with the symmetric Troger's base products. This straightforward approach requires only one chromatographic step and has the potential to replace multi-step

  描述了一系列带有至少一个卤素原子的杂化二苯并 Troger 碱类似物的一步合成。该策略涉及两种不同苯胺之间的反应，并提供产率高达 46% 的杂化化合物，以及对称的 Troger 碱产物。这种直接的方法只需要一个色谱步骤，并且有可能取代混合 Troger 基础化合物的多步骤方法。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• A Joint Theoretical and Experimental Insight into the Electronic Structure of Chromophores Derived from 6H,12H-5,11-Methanodibenzo[b,f][1,5]diazocine
  作者：Vincent Lemaur、Jérôme Cornil、Delphine Didier、Aline Mujawase、Sergey Sergeyev

  DOI：10.1002/hlca.200790216

  日期：2007.11

  electronic spectra of the chiral, donor-acceptor (push-pull) chromophores (±)-4 and (±)-5 with a 6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine scaffold (Scheme 1 and Fig. 2). The electronic structures of these compounds were investigated at a quantum-chemical level (Figs. 2 and 3). The chemical reactivity of 6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine ((±)-11) towards aromatic electrophilic substitution

  我们报告了具有6 H，12 H -5,11-methanodibenzo [ b，f ]的手性，供体-受体（推挽）发色团（±）-4和（±）-5的合成和电子光谱。[1，5]重氮素支架（方案1和图2）。这些化合物的电子结构在量子化学水平上进行了研究（图2和3）。6 H，12 H -5,11-甲二苯并[ b，f ] [1,5]重氮电影（（±）-11）对芳族亲电子取代的化学反应性（方案2和表1）提供了有关其电子结构的更多信息，并证实了在该杂环系统中桥头N原子的孤对的不可忽略的离域。