2-methylphenanthridine | 23002-14-4

• 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-methylphenanthridine
• CAS: 23002-14-4
• 化学式: C₁₄H₁₁N
• 分子量: 193.248
• InChiKey: XJEDMWZLWOWOSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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-methylphenanthridine 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 1.5h， 以65%的产率得到2-bromomethylphenanthridine
  参考文献：
  名称：

  The Selectivity of Reversible Oxy-Anion Binding in Aqueous Solution at a Chiral Europium and Terbium Center:  Signaling of Carbonate Chelation by Changes in the Form and Circular Polarization of Luminescence Emission

  摘要：

  Reversible anion binding in aqueous media at chiral Eu-III and Tbm centers has been characterized by H-1 NMR and by changes in the emission intensity and circular polarization following direct or sensitized (365 nm) excitation via an alkylphenanthridinium chromophore. Using a series of heptadentate tri-amide or polycarboxylate ligands, the affinity for CO32-/HCO3-, phosphate, lactate, citrate, acetate, and malonate at pH 7.4 was found Co decrease as a function of the overall negative charge on the complex: citrate and malonate bound most strongly, and lactate and hydrogen carbonate also formed chelated ternary complexes in, which displacement of both of the metal-bound water molecules occurred, which was confirmed by VT 17-O NMR measurements of-the corresponding Gd complexes. The binding of carbonate was studied in particular, and H-1 NMR and CPL data were obtained that were consistent with the formation of a complex with a reduced helical twist about the metal center. Monohydrogen phosphate was bound in a monodentate manner, giving a mono; aqua adduct. The binding of carbonate to cationic Eu complexes in the presence of a simulated extra-cellular anionic background at pH 7.4 was monitored by variation in the emission intensity, ratio of intensities (615/594 nm), and dissymmetry factors as a function of added total carbonate.

  DOI：

  10.1021/ja001797x
• 作为产物：
  描述：

  4-甲基苯胺盐酸盐 在 selenium 、 乙醇 、 四氯化锡 作用下， 生成 2-methylphenanthridine
  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。
• Carbene-catalyzed aerobic oxidation of isoquinolinium salts: efficient synthesis of isoquinolinones
  作者：Guanjie Wang、Wanyao Hu、Zhouli Hu、Yuxia Zhang、Wei Yao、Lin Li、Zhenqian Fu、Wei Huang

  DOI：10.1039/c8gc01488d

  日期：——

  transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34,

  成功实现了温和环保的卡宾催化的异喹啉鎓盐的好氧氧化。因此，有效地制备了各种异喹啉酮和菲啶酮类，收率良好至优异。机理研究表明，氮杂-布雷斯洛中间体的形成是该转变的关键步骤。该反应具有环境空气作为唯一的氧化剂和氧气源，广泛的底物范围以及出色的官能团耐受性的特点，并且可以在温和的反应条件下进行。此外，生物活性分子和天然产物，包括一种高效合成Ñ -methylcrinasiadine，Ñ -isopentylcrinasiadine，Ñ -phenethylcrinasiadine，异吲哚基[2,1- b完成了] isoquinolin -5（7 H）-1，PJ-34，rac-Gusanlung D，罗塞他星，8-氧代伪巴马汀和伊利福林B的合成。
• A radical addition/cyclization of diverse ethers to 2-isocyanobiaryls under mildly basic aqueous conditions
  作者：Cintia Anton-Torrecillas、Diego Felipe-Blanco、Jose C. Gonzalez-Gomez

  DOI：10.1039/c6ob02103d

  日期：——

  Mildly basic aqueous conditions facilitated the tert-butyl peroxybenzoate (TBPB) mediated dehydrogenative addition of a range of ethers, including acetals, to diverse substituted 2-isocyanobiaryls. Mechanistic studies suggest that this radical cascade is an example of base promoted homolytic aromatic substitution (BHAS).

  温和的碱性水性条件促进了过氧苯甲酸叔丁酯（TBPB）介导的一系列醚（包括缩醛）的脱氢加成到各种取代的2-异氰基双芳基化合物中。机理研究表明，这种自由基级联是碱促进的均相芳族取代（BHAS）的一个例子。
• Transient Imine as a Directing Group for the Metal-Free <i>o</i>-C–H Borylation of Benzaldehydes
  作者：Supriya Rej、Naoto Chatani

  DOI：10.1021/jacs.0c13013

  日期：2021.2.24

  simple metal-free approach, utilizing an imine transient directing group. The strategy covers a wide spectrum of reactions and (i) even highly sterically hindered C–H bonds can be borylated smoothly, (ii) despite the presence of other potential directing groups, the reaction selectively occurs at the o-C–H bond of the benzaldehyde moiety, and (iii) natural products appended to benzaldehyde derivatives can

  Organoboron试剂是重要的合成中间体，在合成有机化学中具有广泛的应用。当前使用的选择性硼化策略很大程度上依赖于过渡金属催化剂的使用。因此，非常需要确定更温和的无过渡金属硼化条件。我们在本文中提出了一种统一的策略，该方法使用一种简单的无金属方法，利用一个亚胺瞬态导向基团，对缺电子的苯甲醛衍生物进行选择性C–H硼化。该策略涵盖了广泛的反应，并且（i）即使是高度空间位阻的C–H键也可以顺利地被硼化，（ii）尽管存在其他潜在的导向基团，但该反应还是选择性地在o处发生。苯甲醛部分的-C–H键，以及（iii）附加到苯甲醛衍生物上的天然产物也可以产生适当的硼化产物。此外，该方案的有效性通过以下事实得以证实：即使在一系列外部杂质的存在下，反应也会进行。
• 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。