5-(trifluoromethyl)benzo[i]phenanthridine | 1440795-39-0

• 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: 5-(trifluoromethyl)benzo[i]phenanthridine
• 英文别名: 5-(Trifluoromethyl)benzo[i]phenanthridine
• CAS: 1440795-39-0
• 化学式: C₁₈H₁₀F₃N
• 分子量: 297.279
• InChiKey: QMKVZBUYGWHAMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三氟甲烷磺酰氯 、 2-(2-isocyanophenyl)naphthalene 在 dipotassium hydrogenphosphate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以51%的产率得到5-(trifluoromethyl)benzo[i]phenanthridine
  参考文献：
  名称：

  Light triggered addition/annulation of 2-isocyanobiphenyls toward 6-trifluoromethyl-phenanthridines under photocatalyst-free conditions

  摘要：

  本文介绍了一种无需光催化剂的高效光促进的2-异氰基联苯顺序自由基加成/环化反应，用于将2-异氰基联苯与6-三氟甲基菲啶进行反应。

  DOI：

  10.1039/c5ra16645d

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。
• 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。
• Light triggered addition/annulation of 2-isocyanobiphenyls toward 6-trifluoromethyl-phenanthridines under photocatalyst-free conditions
  作者：Xiangyang Tang、Shuang Song、Cuibo Liu、Rongjiao Zhu、Bin Zhang

  DOI：10.1039/c5ra16645d

  日期：——

  A photocatalyst-free, light promoted sequential radical addition/annulation of 2-isocyanobiphenyls to 6-trifluoromethyl phenanthridines with high efficiency is presented.

  本文介绍了一种无需光催化剂的高效光促进的2-异氰基联苯顺序自由基加成/环化反应，用于将2-异氰基联苯与6-三氟甲基菲啶进行反应。