5-methylbenzo[c]phenanthridin-6(5H)-one | 24392-33-4

• 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-methylbenzo[c]phenanthridin-6(5H)-one
• 英文别名: 5-Methylbenzo[c]phenanthridin-6-one
• CAS: 24392-33-4
• 化学式: C₁₈H₁₃NO
• 分子量: 259.307
• InChiKey: SYYGFJVVVIBSGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 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：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-甲基苯甲酰胺 在 正丁基锂 、 三甲基氯硅烷 、 sodium iodide 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 13.5h， 生成 5-methylbenzo[c]phenanthridin-6(5H)-one
  参考文献：
  名称：

  Reaction of ortho-lithiated N-methylbenzamide with 1,2-Diketones: A novel highly efficient route to N-methylisoquinolin-1-one

  摘要：

  1,2-Diketones were found to react with ortho-lithiated N-methylbenzamide to give diols 4a-g in 59-80% yields. Reaction of diols 4a-g with the system Me(3)SiCl/Nal in MeCN furnished N-methylisoquinolin-1-ones in 84-92% yields.

  DOI：

  10.1016/0040-4039(94)02293-k

文献信息

• A Novel Synthesis of Benzo(c)phenanthridine Skeleton and Biological Evaluation of Isoquinoline Derivatives.
  作者：Won-Jea CHO、Myun-Ji PARK、Takeshi IMANISHI、Byung-Ho CHUNG

  DOI：10.1248/cpb.47.900

  日期：——

  Benzo[c]phenanthridine skeleton was synthesized from easily available starting N-methyl-o-toluamide 2 and o-methylbenzonitrile 5 in 7 steps. Radical cyclization of styrene 10 afforded 6, 11-dimethyl-6, 11 -dihydro-5H-in-deno[1, 2-c]isoquinolin-5-one 13. Most 3-arylisoquinolines have displayed strong activities against human tumor cell lines. Especially, indenoisoquinolinone 13 exhibited excellent cytotoxicity (IC50=0.002 μg/ml; HCT 15).

  苯并[c]菲啰啉骨架是通过7个步骤由易得的起始物N-甲基-o-苯甲酰胺2和o-甲基苯腈5合成的。苯乙烯10的自由基环化反应生成了6, 11-二甲基-6, 11-二氢-5H-隐苯并[1, 2-c]异喹啉-5-酮13。大多数3-芳基异喹啉对人类肿瘤细胞系表现出了强烈的活性。特别是，隐喹啉酮13表现出优异的细胞毒性（IC50=0.002 μg/ml；HCT 15）。
• Aryl-Aryl Coupling Reaction Using a Novel and Highly Active Palladium Reagent Prepared from Pd(OAc)2, 1,3-Bis[diphenylphosphino]propane (DPPP), and Bu3P.
  作者：Takashi Harayama、Toshihiko Akiyama、Yuichiro Nakano、Hiromi Nishioka、Hitoshi Abe、Yasuo Takeuchi

  DOI：10.1248/cpb.50.519

  日期：——

  A palladium-assisted coupling reaction of aryl triflate with arene was investigated, and a novel Pd reagent prepared from equimolar Pd(OAc)2, 1,3-Bis[diphenylphosphino]propane (DPPP), and Bu3P was developed. This method is useful for intramolecular biaryl coupling reactions, not only between aryl triflate and arene (triflate-amide), but also between aryl halide and arene (halo-amide).

  研究了三氟甲磺酸芳基酯与芳烃的钯辅助偶联反应，并开发了由等摩尔Pd（OAc）2、1,3-双[二苯基膦基]丙烷（DPPP）和Bu3P制备的新型Pd试剂。该方法不仅可用于三氟甲磺酸芳基酯和芳烃（三氟甲酰胺）之间的分子内联芳基偶联反应，而且可用于卤代芳基和芳烃（卤代酰胺）之间的分子内联芳反应。
• Internal Aryl-Aryl Coupling Reaction Using a Novel and Highly Active Palladium Reagent Prepared from Pd(OAc)2, DPPP, and Bu3P.
  作者：Takashi HARAYAMA、Toshihiko AKIYAMA、Yuichiro NAKANO

  DOI：10.1248/cpb.45.1723

  日期：——

  A novel Pd reagent prepared from equimolar Pd(OAc)2, DPPP, and Bu3P (method B) was useful for the internal biaryl coupling reaction of not only triflate-amide but also halo-amide.

  由等摩尔 Pd(OAc)2、DPPP 和 Bu3P 制备的新型钯试剂（方法 B）不仅适用于三氟甲酰胺的内部双芳基偶联反应，也适用于卤代甲酰胺的内部双芳基偶联反应。
• Visible‐Light‐Driven Synthesis of Phenanthridin‐6(5<i>H</i>)‐one and <i>N</i>‐Substituted Carbazole Derivatives through Intramolecular C‐H Arylation
  作者：Micaela Ayelén Cuellar、Micaela Denise Heredia、Guillermo Brarda、Silvia Maricel Barolo、Eva Daniela Díaz Vázquez、Paula Marina Uberman、Sandra Elizabeth Martín、María Eugenia Budén

  DOI：10.1002/ejoc.202300361

  日期：2023.10.9

  The synthesis of phenanthridinones and carbazoles by intramolecular photo- and Base-promoted Homolityc Aromatic Substitution photo-BHAS) reaction from N-(2-halobenzyl)-N-methylanilines or N-substituted-N-phenyl anilines is presented. The synthetic protocol uses only KOtBu and DMSO to generate aryl radicals under visible-light irradiation. An exciplex complex between the substrates and the dimsyl anion

  提出了由N- (2-卤代苄基)-N-甲基苯胺或N-取代-N-苯基苯胺通过分子内光和碱促进的均质芳族取代(光-BHAS)反应合成菲啶酮和咔唑。该合成方案仅使用 KO t Bu 和 DMSO 在可见光照射下产生芳基自由基。底物和二甲基阴离子之间的激基复合物可能参与引发步骤。
• 10.1039/d4ra02835j
  作者：Díaz-Vázquez, Eva D.、Cuellar, Micaela A.、Heredia, Micaela D.、Barolo, Silvia M.、González-Bakker, Aday、Padrón, José M.、Budén, María E.、Martín, Sandra E.、Uberman, Paula M.

  DOI：10.1039/d4ra02835j

  日期：——

  antiproliferative activity of phenanthridine-6(5H)-ones and benzo[c]chromenes was evaluated against six human solid tumor cell lines. The more active compounds exhibit activity in the low micromolar range. 1-Isopropyl-4-methyl-6H-benzo[c]chromene was identified as the best compound with promising values of activity (GI50 range 3.9–8.6 μM). Thus, the benzochromene core was highlighted as a novel organic building

  在本工作中，通过光化学合成的 Pd-PVP 纳米颗粒催化的分子内 C-H 键功能化反应，有效地制备了菲啶-6(5 H )-酮和苯并[ c ]色烯的衍生物。杂环化合物通过相应的N-甲基-N-芳基-2-卤代苯甲酰胺或芳基-(2-卤代)苄基醚的分子内芳基化获得，使用K 2 CO 3作为碱，在H 2 O:DMA作为溶剂的混合物中，没有添加剂或配体。在 100 °C 的空气气氛下，使用适度低的催化剂负载量 (1–5 mol%) 可以实现杂环化合物的高收率（高达 95%）。该反应对不同的官能团（OMe、Me、 t Bu、Ph、OCF 3 、CF 3 、F、Cl、-CN、Naph）表现出非常好的耐受性，并且溴和碘底物均表现出良好的反应活性。最后，评估了菲啶-6(5 H )-酮和苯并[ c ]色烯针对六种人实体瘤细胞系的体外抗增殖活性。活性较高的化合物在低微摩尔范围内表现出活性。 1-异丙基-4-甲基-6