3,6-bis(trifluoromethyl)phenanthridine | 1440795-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3,6-bis(trifluoromethyl)phenanthridine
• 英文别名: 3,6-Bis(trifluoromethyl)phenanthridine
• CAS: 1440795-52-7
• 化学式: C₁₅H₇F₆N
• 分子量: 315.218
• InChiKey: YOQYSXFTILBYTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,2,2-trifluoro-N-[2-phenyl-5-(trifluoromethyl)phenyl]ethanimidoyl chloride 在 tris(bipyridine)ruthenium(II) dichloride hexahydrate 、 三正丁胺 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以80%的产率得到3,6-bis(trifluoromethyl)phenanthridine
  参考文献：
  名称：

  通过可见光介导的三氟乙酰亚胺氯的分子内自由基环化反应制备6-三氟甲基菲啶的方法†

  摘要：

  为合成6-（三氟甲基）菲啶衍生物，开发了一种温和且有效的可见光介导的三氟乙酰亚胺基氯的分子内自由基环化反应。该反应涉及从C（sp 2）-Cl键生成自由基中间体和均溶自由基芳族取代（HAS）过程。

  DOI：

  10.1039/c4ra02384f

文献信息

• Isocyanide Insertion: De Novo Synthesis of Trifluoromethylated Phenanthridine Derivatives
  作者：Yuanzheng Cheng、Heng Jiang、Yan Zhang、Shouyun Yu

  DOI：10.1021/ol4026827

  日期：2013.11

  A mechanistically new strategy has been described for the simple, practical, and environmentally friendly preparation of 6-(trifluoromethyl)phenanthridine derivatives using ionic isocyanide insertion from biphenyl isocyanide derivatives and Umemoto’s reagent. These reactions were promoted only by inorganic base in good-to-excellent chemical yields without any external stoichiometric oxidants and radical

  已经描述了一种机械上新的策略，该方法使用联苯异氰酸酯衍生物和梅本试剂中的离子异氰化物简单，实用且环保地制备了6-（三氟甲基）菲啶衍生物。这些反应仅由无机碱以良好至优异的化学产率促进，而没有任何外部化学计量的氧化剂和自由基引发剂。
• Synthesis of 6-(Trifluoromethyl)phenanthridines via Palladium-Catalyzed Tandem Suzuki/C–H Arylation Reactions
  作者：Wen-Ying Wang、Xia Feng、Bo-Lun Hu、Chen-Liang Deng、Xing-Guo Zhang

  DOI：10.1021/jo4007255

  日期：2013.6.21

  A palladium-catalyzed tandem Suzuki/C–H arylation reaction of N-aryltrifluoroacetimidoyl chlorides with arylboronic acids has been developed. A variety of 6-(trifluoromethyl)phenanthridines were prepared in moderate to excellent yields from N-(2-bromophenyl)trifluoroacetimidoyl chlorides which can be conveniently prepared from 2-bromoaniline derivatives.

  已经开发了钯催化的N-芳基三氟乙酰亚胺基氯化物与芳基硼酸的串联Suzuki / CH芳基化反应。从N-（2-溴苯基）三氟乙酰亚氨基酰氯制备各种6-（三氟甲基）菲啶，产率适中至优异，它们可以方便地由2-溴苯胺衍生物制备。
• Silver-Catalyzed Tandem Trifluoromethylation and Cyclization of Aryl Isonitriles with the Langlois Reagent
  作者：Xing-Guo Zhang、Yu-Rong Liu、Hai-Yong Tu

  DOI：10.1055/s-0034-1378810

  日期：——

  A mild and efficient procedure for the silver-catalyzed tandem trifluoromethylation and cyclization of aryl isonitriles with the Langlois reagent (sodium triflinate) is developed. A series of trifluoro-methylated phenanthridines is prepared in moderate to good yields from a cheap and stable trifluoromethyl source.
• Palladium-catalyzed intramolecular C−H bond functionalization of trifluoroacetimidoyl chloride derivatives: Synthesis of 6-trifluoromethyl-phenanthridines
  作者：Mei Zhu、Weijun Fu、Guanglong Zou、Chen Xu、Zhiqiang Wang

  DOI：10.1016/j.jfluchem.2014.04.005

  日期：2014.7

  Highly efficient approaches to obtain 6-trifluoromethyl-phenanthridine derivatives have been realized through the palladium-catalyzed intramolecular C-H bond functionalization of trifluoroacetimidoyl chlorides. The reaction allows the direct formation of C-sp2-C-sp2 bonds via C-H bond functionalization and rapid access to phenanthridine ring systems in moderate to high yields with good functional group tolerance. (C) 2014 Elsevier B.V. All rights reserved.
• An approach to 6-trifluoromethyl-phenanthridines through visible-light-mediated intramolecular radical cyclization of trifluoroacetimidoyl chlorides
  作者：Weijun Fu、Mei Zhu、Fengjuan Xu、Yuqin Fu、Chen Xu、Dapeng Zou

  DOI：10.1039/c4ra02384f

  日期：——

  A mild and efficient visible light-mediated intramolecular radical cyclization of trifluoroacetimidoyl chlorides is developed for the synthesis of 6-(trifluoromethyl)phenanthridine derivatives. The reaction involves the generation of radical intermediates from C(sp2)–Cl bonds and a homolytic radical aromatic substitution (HAS) process.

  为合成6-（三氟甲基）菲啶衍生物，开发了一种温和且有效的可见光介导的三氟乙酰亚胺基氯的分子内自由基环化反应。该反应涉及从C（sp 2）-Cl键生成自由基中间体和均溶自由基芳族取代（HAS）过程。