2-methoxyphenanthridine | 41001-65-4

• 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: 2-methoxyphenanthridine
• CAS: 41001-65-4
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: UCNSZVGVHIPUFQ-UHFFFAOYSA-N

物化性质

• 熔点：
  57-58 °C
• 沸点：
  387.7±15.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methoxyphenanthridine 在 sodium chloride 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 水 、 硝基苯 为溶剂， 反应 1.0h， 生成 2-Methoxy-5-methylphenanthridin-5-ium;chloride
  参考文献：
  名称：

  Synthesis, topoisomerase-targeting activity and growth inhibition of lycobetaine analogs

  摘要：

  The plant alkaloid lycobetaine has potent topoisomerase-targeting properties and shows anticancer activity. Based on these findings, several lycobetaine analogs were synthesized mainly differing in their substituents at 2, 8 and 9 position and their biological activities were evaluated. The topoisomerase-targeting properties and cytotoxicity of these structural analogs were assessed in the human gastric carcinoma cell line GXF251L. Performing a plasmid relaxation assay, an increased inhibition of topoisomerase I was found with N-methylphenanthridinium chlorides bearing a 8,9-methylenedioxy moiety or a methoxy group in 2-position. Furthermore, quaternized phenanthridinium derivatives bearing either a 2-methoxy or a 8,9-methylenedioxy moiety in conjunction with a 2-hydroxy or 2-methoxy group display potent topoisomerase II inhibition as shown by decatenation of kinetoplast DNA. In general, the N-methylphenanthridinium chlorides possess more potency in inhibiting topoisomerase I than topoisomerase II. All quaternized derivatives also exhibited potent inhibition of tumor cell growth in the low micromolar concentration range. Hence, N-methylphenanthridinium compounds were found to represent a promising class of compounds, potently inhibiting both, topoisomerases I and II, and may be further developed into clinically useful topoisomerase inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.011
• 作为产物：
  描述：

  邻溴苄胺 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 碘苯二乙酸 、 碘 、 三乙胺 作用下， 以 乙二醇二甲醚 、 硝基甲烷 、 二氯甲烷 、 水 为溶剂， 反应 29.0h， 生成 2-methoxyphenanthridine
  参考文献：
  名称：

  通过碘支持的分子内CH胺化和在可见光下的氧化反应合成菲啶。

  摘要：

  在这里，我们报告了在温和的条件下从2-biarylmethanamines无金属和经济的步骤合成菲啶。该反应包括碘在空气和良性可见光下的分子内CH–H胺化和5,6-二氢菲啶的氧化。机制研究表明，可见光在这两个步骤中都起着关键作用。

  DOI：

  10.1021/acs.joc.0c01390

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。
• Visible-Light-Promoted Iminyl-Radical Formation from Acyl Oximes: A Unified Approach to Pyridines, Quinolines, and Phenanthridines
  作者：Heng Jiang、Xiaode An、Kun Tong、Tianyi Zheng、Yan Zhang、Shouyun Yu

  DOI：10.1002/anie.201411342

  日期：2015.3.23

  iminyl‐radical formation has been established for the construction of pyridines, quinolines, and phenanthridines from acyl oximes. With fac‐[Ir(ppy)3] as a photoredox catalyst, the acyl oximes were converted by 1 e− reduction into iminyl radical intermediates, which then underwent intramolecular homolytic aromatic substitution (HAS) to give the N‐containing arenes. These reactions proceeded with a broad

  已经建立了涉及可见光诱导的亚胺基自由基形成的统一策略，用于从酰基肟中构建吡啶，喹啉和菲啶。用FAC - [的Ir（ppy）3 ]作为催化剂photoredox，酰基肟通过1e中转化-还原成亚氨基自由基中间体，然后行分子内均裂芳族取代（HAS），得到含有N-芳烃其中。这些反应在室温下以宽范围的底物以高收率进行。这种可见光诱导的亚胺基自由基形成策略已成功地应用于五步精简合成苯并[ c ]菲啶生物碱。
• Photocyclization synthesis of phenanthridine and its derivatives under direct dehydrogenation conditions
  作者：Wen-Qing Zhu、Jin Zhang、Pan Fan、Lan-Ting Shi、Hong Li、Min-Ge Yang、Yang Li

  DOI：10.1016/j.tetlet.2020.152734

  日期：2021.2

  synthesizing phenanthridines by photocyclization has been established. This method does not require inert gas protection, does not require transition metal catalysts and is environmentally friendly, efficient and convenient. It is proposed to use (E)-N,1-diphenylformimines as substrates to synthesize phenanthridine and its derivatives by ultraviolet light, which provides a new synthesis route for further research

  建立了一种通过光环化合成菲啶的新方法。该方法不需要惰性气体保护，不需要过渡金属催化剂，并且是环境友好，有效和方便的。提出以（E）-N，1-二苯基甲亚胺为底物通过紫外光合成菲啶及其衍生物，为进一步研究光环化合成菲啶提供了一条新的合成途径。合成了八种新的菲啶化合物。其结构的确认为进一步研究其性能和挖掘其应用潜力提供了物质基础。该方法的建立进一步拓宽了菲啶化合物的合成途径。
• A ruthenium-catalyzed free amine directed (5+1) annulation of anilines with olefins: diverse synthesis of phenanthridine derivatives
  作者：Deepan Chowdhury、Suman Dana、Anup Mandal、Mahiuddin Baidya

  DOI：10.1039/c9cc05717j

  日期：——

  annulation between 2-aminobiphenyls and activated olefins is disclosed for succinct synthesis of valuable phenanthridine scaffolds. The protocol avails a common organic functional group, free amine, as a directing group and represents a unique combination of C–H activation/annulation/C–C bond cleavage cascade that bodes well in the production of bioactive alkaloids including trisphaeridine and bicolorine

  公开了2-氨基联苯和活化的烯烃之间的钌（II）催化的交叉环（5 + 1）环化，用于简洁地合成有价值的菲啶骨架。该方案利用一个常见的有机官能团，即游离胺作为指导基团，代表了C–H活化/环化/ C–C键裂解级联的独特组合，预示着生物活性生物碱（包括三叶啶和双色氨酸）的产生。
• 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。