(+/-)-2,8-dimethoxy-N,N-dimethyl-6H,12H-5,11-methanodibenzo-[b,f][1,5]diazocin-13-amine | 1338997-08-2

• 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: (+/-)-2,8-dimethoxy-N,N-dimethyl-6H,12H-5,11-methanodibenzo-[b,f][1,5]diazocin-13-amine
• 英文别名: 2,8-dimethoxy-13-(N,N-dimethylamino)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine；5,13-dimethoxy-N,N-dimethyl-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10(15),11,13-hexaen-17-amine
• CAS: 1338997-08-2
• 化学式: C₁₉H₂₃N₃O₂
• 分子量: 325.411
• InChiKey: ZHCGTSVQJKKHGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,8-dimethoxy-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine 、 N,N-二甲基甲酰胺 在 三氯氧磷 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以84%的产率得到(+/-)-2,8-dimethoxy-N,N-dimethyl-6H,12H-5,11-methanodibenzo-[b,f][1,5]diazocin-13-amine
  参考文献：
  名称：

  通过甲醇桥与羰基化合物的交换从Tröger碱合成新衍生物

  摘要：

  已经开发了一种简单的一锅法，用于通过在TiCl 4或POCl 3的存在下与rac- Tröger碱衍生物的甲醇桥与羰基化合物进行交换反应来制备新的Tröger碱衍生物。使用手性（S，S）-N，N-双（α-甲基苄基）甲酰胺作为羰基化合物可得到相应的亚甲基Tröger碱衍生物，其非对映体比例高达77:23。

  DOI：

  10.1016/j.tetasy.2012.01.009

文献信息

• Regioselective Synthesis of Dimethylamino- or Arylalkylamino-‘‘Crowned” Tröger's Base Analogues Under Vilsmeier-Haack Conditions
  作者：Manda Bhaskar Reddy、Alla Manjula、Bommena Vittal Rao、Balasubramanian Sridhar

  DOI：10.1002/ejoc.201100804

  日期：2012.1

  Under typical Vilsmeier–Haack conditions, Troger's base undergoes regioselective dimethylamino or arylalkylamino substitution on the methano bridge of the dibenzo[b,f][1,5]diazocine system, revealing a hitherto unknown reactivity pattern. The regioselectivity of the reaction was established by NMR spectroscopy and X-ray crystallography. The key feature of this reaction is its generality; it is compatible

  在典型的 Vilsmeier-Haack 条件下，Troger 的碱在二苯并 [b,f][1,5] 重氮辛系统的甲烷桥上发生区域选择性二甲氨基或芳烷基氨基取代，揭示了迄今为止未知的反应模式。反应的区域选择性是通过核磁共振光谱和 X 射线晶体学确定的。这种反应的主要特点是它的普遍性；它与 Troger 底座上的不同取代模式兼容，并且可以与 DMF 以及其他甲酰胺一起使用。该反应的广泛范围已被用于合成几种不常见的 Troger 碱类似物。
• Discovery of Tröger's base analogues as selective inhibitors against human breast cancer cell line: Design, synthesis and cytotoxic evaluation
  作者：Bhaskar Reddy Manda、Manjula Alla、Roopa Jones Ganji、Anthony Addlagatta

  DOI：10.1016/j.ejmech.2014.08.044

  日期：2014.10

  A library of structurally diverse Troger's base analogues has been constructed via unusual amination of methylene bridge employing Vilsmeier-Haack conditions as well as by the incorporation of five and six membered heterocycles on the aromatic core of Troger's base framework. The constructed structurally diverse frameworks were evaluated for their cytotoxic activities against a panel of three human cancer lines A549 (lung adenocarcinoma), MDAMB-231 (breast) and SK-N-SH (neuroblastoma). From the activity profile obtained, a redesign of Troger's base analogues led to the construction of more potent molecular entities. The study led to development of a series of compounds with MDAMB-231 cell line specific cytotoxicity. Of the 30 compounds synthesized and evaluated, 7 compounds were found to possess cytotoxicity that is equivalent or better than standard drug doxorubicin against MDAMB-231 cell line while only one compound was found to be active against SK-N-SH cell line. (c) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis of new derivatives from a Tröger base via exchange of the methano bridge with carbonyl compounds
  作者：Mariappan Periasamy、Sundaram Suresh、Sakilam Satishkumar

  DOI：10.1016/j.tetasy.2012.01.009

  日期：2012.1

  method has been developed for the preparation of new Tröger base derivatives by an exchange reaction with the methano bridge of rac-Tröger base derivatives with carbonyl compounds in the presence of TiCl4 or POCl3. The use of chiral (S,S)-N,N-bis(α-methylbenzyl)formamide as a carbonyl compound gave the corresponding methano Tröger base derivatives with the diastereomeric ratios of up to 77:23.

  已经开发了一种简单的一锅法，用于通过在TiCl 4或POCl 3的存在下与rac- Tröger碱衍生物的甲醇桥与羰基化合物进行交换反应来制备新的Tröger碱衍生物。使用手性（S，S）-N，N-双（α-甲基苄基）甲酰胺作为羰基化合物可得到相应的亚甲基Tröger碱衍生物，其非对映体比例高达77:23。