N-methylbenzophenanthridone | 74480-79-8

• 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: N-methylbenzophenanthridone
• 英文别名: 5-methylbenzo[k]phenanthridin-6(5H)-one；N-Methyl-5,6-benzophenanthridon；N-Methyl-9,10-benzo-phenanthridon-(6)；5-methyl-5H-benzo[k]phenanthridin-6-one；5-Methyl-5H-benzo[k]phenanthridin-6-on；5-Methylbenzo[k]phenanthridin-6-one
• CAS: 74480-79-8
• 化学式: C₁₈H₁₃NO
• 分子量: 259.307
• InChiKey: KQPGCOJTXQEGHP-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：

  3-styryl-N-methyl-2-quinolone 在 碘 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以65%的产率得到N-methylbenzophenanthridone
  参考文献：
  名称：

  Synthesis of Benzo[k]phenanthridines: Another New Approach

  摘要：

  DOI：

  10.1055/s-1981-29612

文献信息

• Samarium(II)-Mediated Spirocyclization by Intramolecular Aryl Radical Addition onto an Aromatic Ring
  作者：Hiroki Iwasaki、Toru Eguchi、Nozomi Tsutsui、Hiroaki Ohno、Tetsuaki Tanaka

  DOI：10.1021/jo800656a

  日期：2008.9.19

  Samarium(II)-mediated spirocyclization by intramolecular addition of aryl radicals onto an aromatic ring was achieved by the reaction of N-(2-iodophenyl)-N-alkylbenzamides with SmI2 in the presence of HMPA, yielding spirocyclic indolin-2-one derivatives. The ether congeners afford spirocyclic benzofuran derivatives in moderate yields by aryl radical addition onto a benzene ring without having an electron-withdrawing

  N-（2-碘苯基）-N-烷基苯甲酰胺与SmI2在HMPA存在下反应，通过在芳环上分子内加成芳基，将mar（II）介导的螺环化反应，生成螺环吲哚-2-酮衍生物。醚同类物通过在不具有吸电子基团的情况下将芳基自由基加成到苯环上而以中等收率得到螺环苯并呋喃衍生物。还描述了与其他芳基如萘和吲哚环的反应。
• Pd/Cu-Catalyzed aerobic oxidative aromatic C–H bond activation/N-dealkylative carbonylation towards the synthesis of phenanthridinones
  作者：Renyi Shi、Huiying Niu、Lijun Lu、Aiwen Lei

  DOI：10.1039/c6cc08701a

  日期：——

  A straightforward Pd/Cu-catalyzed oxidative C–H bond activation/N-dealkylative carbonylation of tertiary [1,1′-biphenyl]-2-anilines towards the synthesis of various biologically important phenanthridin-6(5H)-ones has been developed. A wide range of functional groups are well tolerated in this transformation.

  一种直接的Pd/Cu催化氧化C-H键活化/N-去烷基羰基化反应已被开发，用于合成各种生物重要的苯并噻吩-6(5H)-酮。在这一转化中，广泛的官能团被很好地容忍。
• One-pot synthesis of benzo[a]phenanthridin-5-ones by photoinduced cycloaddition of 3-chloroisoquinolin-1-ones with styrenes
  作者：Bing Li、Bing Han、Zong-jun Shi、Yu-wei Ren、Shen-ci Lu、Wei Zhang

  DOI：10.1016/j.tetlet.2010.05.037

  日期：2010.7

  es and benzo[k]phenanthridin-6-ones in fairly good yields was achieved by the photocycloaddition reactions of 3-chloroisoquinolin-1-ones and 3-chloroquinolin-2-ones with styrenes. The reactions were proceeded via photoinduced dechlorinative coupling of 3-chloroisoquinolin-1-ones and 3-chloroquinolin-2-ones with styrenes and subsequent photocyclization, oxidative aromatization.

  通过3-氯异喹啉-1-酮和3-氯喹啉-2-酮的光环加成反应，可以一锅法合成苯并[ a ]菲咯啉-5-酮和苯并[ k ]菲咯啉-6-酮。与苯乙烯。通过3-氯异喹啉-1-酮和3-氯喹啉-2-酮与苯乙烯的光致脱氯偶合以及随后的光环化，氧化芳构化来进行反应。
• Pd-catalyzed dehydrogenative annulation approach for the efficient synthesis of phenanthridinones
  作者：Xinyao Li、Jun Pan、Song Song、Ning Jiao

  DOI：10.1039/c6sc01148a

  日期：——

  annulation of aryl iodides and aryl carbamic chlorides for the efficient synthesis of phenanthridinone derivatives was developed. Simple aryl iodides and carbamic chlorides readily made from various anilines, a broad substrate scope with hetero/polycycles, as well as high-value products, make this direct dehydrogenative annulation approach very practical and attractive.

  开发了一种新型的钯催化的芳基碘化物和芳基氨基甲酸酯氯化物的分子间脱氢环化反应，以有效地合成菲啶酮衍生物。由各种苯胺容易制得的简单的芳基碘化物和氨基甲酸酯氯化物，具有杂/多环的广泛底物范围以及高价值的产品，使得这种直接的脱氢环化方法非常实用且具有吸引力。
• A Visible-Light-Induced α-Aminoalkyl-Radical-Mediated Halogen-Atom Transfer Process: Modular Synthesis of Phenanthridinone Alkaloids
  作者：Karunamayee Mondal、Sumitava Mallik、Sunaina Sardana、Mahiuddin Baidya

  DOI：10.1021/acs.orglett.3c00358

  日期：2023.3.17

  A halogen-atom transfer (XAT) strategy utilizing α-aminoalkyl radicals allows the generation of aryl radicals at room temperature, which is applied for intramolecular cyclization reactions en route to biologically relevant alkaloids. Starting from simple halogen-substituted benzamides under visible light irradiation in the presence of an organophotocatalyst (4CzIPN) and nBu3N allows the modular construction

  利用 α-氨基烷基自由基的卤素原子转移 (XAT) 策略允许在室温下产生芳基自由基，用于分子内环化反应，生成生物学相关的生物碱。在有机光催化剂 (4CzIPN) 和n Bu 3 N 存在下，从可见光照射下的简单卤素取代苯甲酰胺开始，可以构建菲啶酮核心的模块化结构，从而可以轻松获得药物类似物和生物碱，例如，来自石蒜科的药物类似物和生物碱. 反应途径很可能涉及启用量子力学隧穿的转移事件，以实现芳构化-卤素-原子转移。