2,4-dimethylphenanthridine | 861002-62-2

• 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: 2,4-dimethylphenanthridine
• 英文别名: 2,4-Dimethylphenanthridine
• CAS: 861002-62-2
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: ZCJJCCPHHHBADP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  2,4-dimethylphenanthridine 在 sodium amide 、 N,N-二乙基苯胺 作用下， 生成 2,4-dimethyl-6-phenanthridinamine
  参考文献：
  名称：

  309.杂环化合物的新合成。第九部分。四氢菲啶

  摘要：

  DOI：

  10.1039/jr9480001537
• 作为产物：
  描述：

  2-(羟基甲基)环己酮 在 selenium 、 四氯化锡 作用下， 生成 2,4-dimethylphenanthridine
  参考文献：
  名称：

  Kenner et al., Journal of the Chemical Society, 1937, p. 1169,1172

  摘要：

  DOI：

文献信息

• Synthesis of Phenanthridines through Palladium-Catalyzed Cascade Reaction of 2-Halo-<i>N</i>-Ms-arylamines with Benzyl Halides/Sulfonates
  作者：Si-Yi Yang、Wen-Yong Han、Ding-Lei Zhang、Xiao-Jian Zhou、Mei Bai、Bao-Dong Cui、Nan-Wei Wan、Wei-Cheng Yuan、Yong-Zheng Chen

  DOI：10.1002/ejoc.201601608

  日期：2017.2.3

  An efficient palladium-catalyzed nucleophilic substitution/C–H activation/aromatization cascade reaction between readily available 2-halo-N-Ms-arylamines (Ms = methanesulfonyl) and benzyl halides/sulfonates has been described. A wide variety of phenanthridines were synthesized in a one-pot fashion in moderate to high yields (37–86 %). Notably, this method provides a straightforward, facile approach

  已经描述了容易获得的 2-卤代-N-Ms-芳基胺（Ms = 甲磺酰基）和苄基卤化物/磺酸盐之间的有效钯催化亲核取代/C-H 活化/芳构化级联反应。以一锅法以中等至高产率 (37–86%) 合成了多种菲啶。值得注意的是，该方法为菲啶的合成提供了一种直接、简便的方法。通过成功进行克级制备进一步证实了实用性。
• Domino Suzuki coupling and condensation reaction: an efficient strategy towards synthesis of phenanthridines
  作者：Munmun Ghosh、Atiur Ahmed、Raju Singha、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2014.11.092

  日期：2015.1

  A short and convenient hetero-annulation protocol has been developed for the synthesis of substituted phenanthridines via domino Suzuki coupling and condensation between N-(2-iodo-aryl)-formamide derivatives and 2-formylphenylboronic acid in the presence of Pd(OAc)2, Cs2CO3 and PPh3 as catalytic system in dry DMF at 85–90 °C for 6–7 h. The intermediate after Suzuki coupling and deprotection of nitrogen

  已经开发了一种短而方便的异环合成方案，用于在Pd（OAc）2存在下通过多米诺Suzuki偶联和N-（2-碘-芳基）-甲酰胺衍生物与2-甲酰基苯基硼酸之间的缩合合成取代的菲啶。，Cs 2 CO 3和PPh 3作为干燥DMF在85–90°C下反应6–7 h的催化体系。在相同的催化系统下，铃木偶联和氮脱保护后的中间体，在立即缩合和脱水后，便以高收率提供了相应的菲啶。
• Metal-Free Photoredox Catalyzed Cyclization of O-(2,4-Dinitrophenyl)oximes to Phenanthridines
  作者：Xiubin Liu、Zhixing Qing、Pi Cheng、Xinyu Zheng、Jianguo Zeng、Hongqi Xie

  DOI：10.3390/molecules21121690

  日期：——

  A metal-free visible-light photoredox-catalyzed intermolecular cyclization reaction of O-2,4-dinitrophenyl oximes to phenanthridines was developed. In this study, the organic dye eosin Y and i-Pr₂NEt were used as photocatalyst and terminal reductant, respectively. The oxime substrates were transformed into iminyl radical intermediates by single-electron reduction, which then underwent intermolecular

  开发了一种无金属的可见光光氧化还原催化的O-2,4-二硝基苯基肟与菲啶的分子间环化反应。在这项研究中，有机染料曙红Y和i-Pr 2 NEt分别用作光催化剂和末端还原剂。通过单电子还原将肟底物转化为亚氨基自由基中间体，然后使其进行分子间均溶芳族取代（HAS）反应，得到菲啶衍生物。
• Palladium-Catalyzed Nucleophilic Substitution/C–H Activation/Aromatization Cascade Reaction: One Approach To Construct 6-Unsubstituted Phenanthridines
  作者：Wenyong Han、Xiaojian Zhou、Siyi Yang、Guangyan Xiang、Baodong Cui、Yongzheng Chen

  DOI：10.1021/acs.joc.5b02145

  日期：2015.11.20

  A facile and practical palladium-catalyzed nucleophilic substitution/C–H activation/aromatization cascade reaction has been developed. A range of 6-unsubstituted phenanthridines could be obtained in moderate to good yields (31–85%) with readily prepared N-Ms arylamines and commercially available 2-bromobenzyl bromide derivatives as starting materials. The potential application of the protocol was also

  已经开发了一种简便实用的钯催化亲核取代/ CH活化/芳构化级联反应。以现成的N - Ms芳基胺和可商购的2-溴苄基溴衍生物为原料，可以以中等至良好的收率（31-85％）获得一系列6-未取代的菲啶。该协议的潜在应用还通过天然生物碱三香精的快速合成得到了证明。
• Expeditious Synthesis of Phenanthridines from Benzylamines via Dual Palladium Catalysis
  作者：Giovanni Maestri、Marie-Hélène Larraufie、Étienne Derat、Cyril Ollivier、Louis Fensterbank、Emmanuel Lacôte、Max Malacria

  DOI：10.1021/ol102509n

  日期：2010.12.17

  A method for the synthesis of phenanthridines from benzylamines and aryl iodides which uses a dual palladium-catalyzed process is developed. The domino sequence ends via an intramolecular amination and an oxidative dehydrogenation. No protecting group or prefunctionalization of the amine is required, and the process uses dioxygen as the terminal oxidant.