4-methyl-6-phenylphenanthridine | 112421-99-5

• 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: 4-methyl-6-phenylphenanthridine
• CAS: 112421-99-5
• 化学式: C₂₀H₁₅N
• 分子量: 269.346
• InChiKey: OKYINCKSYVWKDA-UHFFFAOYSA-N

物化性质

• 熔点：
  114.5-115.5 °C(Solv: ligroine (8032-32-4))
• 沸点：
  443.5±14.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methyl-6-phenylphenanthridine 在 chromium(VI) oxide 、 硫酸 、 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 4-Phenanthridinecarboxamide, N-(2-(dimethylamino)ethyl)-6-phenyl-
  参考文献：
  名称：

  Potential antitumor agents. 55. 6-Phenylphenanthridine-4-carboxamides: a new class of DNA-intercalating antitumor agents

  摘要：

  Derivatives of the DNA-intercalating agent N-[2-(dimethylamino)ethyl]phenanthridine-4-carboxamide have been prepared and shown to have moderate in vivo antitumor activity against both the P388 leukemia and Lewis lung carcinoma. This demonstrates that the effective pharmacophore in the broad class of tricyclic carboxamides is not limited to linear tricyclic chromophores. Both 7 and the 6-phenyl derivative 10 have identical DNA binding properties, suggesting that the phenyl ring of 10 is not involved in the DNA intercalation site. A series of phenyl-substituted derivatives of 10 was evaluated. Aza substituents led to compounds with the highest in vivo cytotoxicity and in vivo P388 activity, but the in vivo solid tumor activity of the substituted 6-phenylphenanthridine-4-carboxamides was in general low.

  DOI：

  10.1021/jm00399a015
• 作为产物：
  描述：

  2-碘氰基苯 在 bis-triphenylphosphine-palladium(II) chloride 、 正丁基锂 、 碘 、 potassium carbonate 、 六甲基二硅氮烷 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 37.0h， 生成 4-methyl-6-phenylphenanthridine
  参考文献：
  名称：

  芳基邻联芳基酮中的6-芳基菲啶与1,1,1,3,3,3-六甲基二硅氮杂和分子碘

  摘要：

  在甲苯中Sc（OTf）3存在下，通过与1,1,1,1,3,3,3-六甲基二硅氮烷反应，将芳基联芳基酮有效地转化为6-芳基菲啶，然后除去溶剂，然后进行后续反应分子碘和THF和甲醇的混合物中的K 2 CO 3。

  DOI：

  10.1002/ejoc.201901278

文献信息

• Preparation of Phenanthridines from <i>o</i>-Cyanobiaryls via Addition of Organic Lithiums to Nitriles and Imino Radical Cyclization with Iodine
  作者：Atsushi Kishi、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1021/acs.joc.8b01688

  日期：2018.9.21

  methyllithium, ethylmagnesium bromide, butyllithium, phenyllithium, p-methylphenyllithium, etc., followed by the reaction with water and then with molecular iodine at 60 °C provided efficiently 6-methyl-, 6-ethyl-, 6-butyl-, 6-phenyl, 6-(p-methylphenyl)phenanthridines, etc., in good yields, respectively. Here, imines formed through the addition of carbanion onto the nitriles reacted with molecular iodine

  用甲基锂，乙基溴化镁，丁基锂，苯基锂，对甲基苯基锂等对2-氰基联芳基进行简单处理，然后与水反应，然后在60°C下与分子碘反应，可有效提供6-甲基-，6-乙基-，分别以良好的收率得到6-丁基-，6-苯基，6-（对甲基苯基）菲啶等。在这里，通过在腈上加碳负离子而形成的亚胺与分子碘反应，平稳地形成N-碘亚胺，并且它们的加温处理诱导了亚胺基的形成，该亚胺基顺利地环化到芳基上，得到6烷基和6芳基菲啶。
• Palladium-Catalyzed Intramolecular C(sp²)-H Imidoylation for the Synthesis of Six-Membered N-Heterocycles
  作者：Jing Li、Yimiao He、Shuang Luo、Jian Lei、Jian Wang、Zeqiang Xie、Qiang Zhu

  DOI：10.1021/jo502731n

  日期：2015.2.20

  containing a pending isocyanide moiety under palladium catalysis, has been developed. This process involves sequential intermolecular isocyanide insertion to an aryl palladium(II) intermediate and intramolecular aromatic C–H activation as key steps. Alkyl palladium(II) intermediate lacking β-hydrogen is also applicable to this reaction, generating unique bisheterocyclic scaffolds with three C–C bonds being

  已经开发了一种新的构建菲啶和异喹啉骨架的策略，该策略从在钯催化下含有未决异氰酸酯部分的芳烃开始。该过程涉及将分子间异氰化物顺序插入芳基钯（II）中间体和分子内芳族CH活化作为关键步骤。缺少β-氢的烷基钯（II）中间体也可用于该反应，生成具有三个连续C-C键的独特双环骨架。
• Copper‐Catalyzed Aerobic Benzylic C(sp3)−H Oxidation of Unprotected Aniline Derivatives for the Synthesis of Phenanthridines
  作者：Kanako Nozawa‐Kumada、Yuta Matsuzawa、Masahito Hayashi、Takumi Kobayashi、Masanori Shigeno、Akira Yada、Yoshinori Kondo

  DOI：10.1002/adsc.202400059

  日期：2024.5.21

  Herein, we report a copper‐catalyzed intramolecular benzylic C(sp3)−H oxidation of unprotected aniline derivatives under aerobic conditions, which enables the preparation of phenanthridine compounds. To the best of our knowledge, this is the pioneering reaction of dehydrogenative C(sp3)−N bond formation from unprotected anilines under a Cu/O2 system. Notably, various anilines possessing alkyl, methoxy

  在此，我们报道了在有氧条件下铜催化未保护的苯胺衍生物的分子内苄基C(sp3)−H氧化，从而能够制备菲啶化合物。据我们所知，这是在 Cu/O2 体系下由未保护的苯胺形成脱氢 C(sp3)−N 键的开创性反应。值得注意的是，具有烷基、甲氧基、卤素（氟、氯、溴和碘）、三氟甲基、三氟甲氧基、氰基、酯和缩醛基团的各种苯胺也可以参与该反应。
• ATWELL, GRAHAM J.;BAGULEY, BRUCE C.;DENNY, WILLIAM A., J. MED. CHEM., 31,(1988) N 4, 774-779
  作者：ATWELL, GRAHAM J.、BAGULEY, BRUCE C.、DENNY, WILLIAM A.

  DOI：——

  日期：——