6-(4-N,N-dimethylaminophenyl)-phenanthridine | 37867-75-7

• 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: 6-(4-N,N-dimethylaminophenyl)-phenanthridine
• 英文别名: N,N-dimethyl-4-(phenanthridin-6-yl)aniline；6-(4-dimethylaminophenyl)phenanthridine；N,N-dimethyl-4-phenanthridin-6-yl-aniline；N,N-Dimethyl-4-phenanthridin-6-yl-anilin；Benzenamine, N,N-dimethyl-4-(6-phenanthridinyl)-；N,N-dimethyl-4-phenanthridin-6-ylaniline
• CAS: 37867-75-7
• 化学式: C₂₁H₁₈N₂
• 分子量: 298.387
• InChiKey: GUNJAKUTKIFMFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  480.3±33.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(4-N,N-dimethylaminophenyl)-phenanthridine 、 硫酸二甲酯 在 硝基苯 作用下， 生成 5-methyl-6-(4-trimethylammonio-phenyl)-phenanthridinium; diiodide
  参考文献：
  名称：

  78.菲啶系列的研究。第五部分季盐的颜色和防腐性能

  摘要：

  DOI：

  10.1039/jr9380000389
• 作为产物：
  描述：

  2-碘联苯 在 copper(II) bis(trifluoromethanesulfonate) 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 22.0h， 生成 6-(4-N,N-dimethylaminophenyl)-phenanthridine
  参考文献：
  名称：

  Synthesis of phenanthridine derivatives via cascade annulation of diaryliodonium salts and nitriles

  摘要：

  已开发出一种针对多种菲啶衍生物的级联偶联反应。该级联转化过程通过二芳基碘鎓盐和腈的铜催化偶联反应进行，并经历环化形成菲啶核心结构。

  DOI：

  10.1039/c4ob01504e

文献信息

• Convergent Synthesis of 6-Substituted Phenanthridines via Anionic Ring Closure
  作者：Morten Lysén、Jesper L. Kristensen、Per Vedsø、Mikael Begtrup

  DOI：10.1021/ol0170051

  日期：2002.1.1

  [reaction: see text] The addition of organometallic derivatives to the cyano group of 2-(2-fluorophenyl)benzonitrile followed by intramolecular nucleophilic substitution produces 6-substituted phenanthridines. Alkyllithiums, aryllithiums, and sterically nondemanding lithium amides reacted at -78 degrees C to produce the 6-substituted phenanthridines in 82-98% yield upon warming to room temperature

  [反应：见正文]将有机金属衍生物加到2-（2-氟苯基）苄腈的氰基上，然后进行分子内亲核取代，生成6-取代的菲啶。烷基锂，芳基锂和空间上不需要的锂酰胺在-78℃下反应，在升温至室温时以82-98％的产率产生6-取代的菲啶。相应的格氏试剂的添加需要过量的有机金属试剂并在高温下延长反应时间。
• Palladium and radical routes to phenanthridines
  作者：W. Russell Bowman、Jessica E. Lyon、Gareth J. Pritchard

  DOI：10.3998/ark.5550190.0013.714

  日期：——

  Two routes to phenanthridines are reported; a palladium-mediated route using imidoyl-selanides as precursors and a modified radical route using aryl imines as starting materials.

  报道了两种获得菲啶的途径；使用亚胺基硒化物作为前体的钯介导的路线和使用芳基亚胺作为起始材料的改性自由基路线。
• Palladium-Mediated Synthesis of Phenanthridines: The First Report of Palladium Insertion into Imidoyl Selenides
  作者：Gareth Pritchard、W. Bowman、Jessica Lyon

  DOI：10.1055/s-2008-1078246

  日期：2008.8

  Imidoyl phenyl selenides have been shown to be precursors to phenanthridines, when treated with Pd(PPh 3 ) 4 under reflux in toluene in the presence of a base, giving reasonable yields. It is proposed that insertion of palladium into the C-Se bond is followed by cyclisation onto a phenyl ring and subsequent aromatisation by elimination of HPdSePh.

  亚胺酰基苯基硒化物已被证明是菲啶的前体，当在甲苯中在碱存在下回流下用 Pd(PPh 3 ) 4 处理时，得到合理的产率。建议将钯插入 C-Se 键，然后环化到苯环上，然后通过消除 HPdSePh 进行芳构化。
• Metal-Free Nitrogenation of 2-Acetylbiphenyls: Expeditious Synthesis of Phenanthridines
  作者：Conghui Tang、Yizhi Yuan、Ning Jiao

  DOI：10.1021/acs.orglett.5b00797

  日期：2015.5.1

  An intermolecular nitrogenation reaction toward the synthesis of phenanthridines has been developed. This metal-free protocol provides a novel nitrogen-incorporation transformation using azides as the nitrogen source. Phenanthridines, which are of great interest in pharmaceutical and medicinal chemistry, are synthesized efficiently in one step. Moreover, the byproducts derived from the Schmidt reaction are inhibited, which further demonstrated the high chemoselectivity of this transformation.
• Katritzky, Alan R.; Yang, Baozhen, Journal of Heterocyclic Chemistry, 1996, vol. 33, # 3, p. 607 - 610
  作者：Katritzky, Alan R.、Yang, Baozhen

  DOI：——

  日期：——