7-methylphenanthridine | 34635-71-7

• 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: 7-methylphenanthridine
• CAS: 34635-71-7
• 化学式: C₁₄H₁₁N
• 分子量: 193.248
• InChiKey: JKXSMHTXKKMNJO-UHFFFAOYSA-N

物化性质

• 熔点：
  87.5-88 °C(Solv: ligroine (8032-32-4))
• 沸点：
  365.3±11.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

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

• 作为产物：
  描述：

  1-(2-methyl-benzyl)-1H-benzo[d][1,2,3]triazole 在 铜 作用下， 生成 7-methylphenanthridine
  参考文献：
  名称：

  Notes

  摘要：

  DOI：

  10.1039/jr9560001076

文献信息

• Expeditious synthesis of phenanthridines through a Pd/MnO₂-mediated C–H arylation/oxidative annulation cascade from aldehydes, aryl iodides and amino acids
  作者：Jian Fan、Li Li、Jitan Zhang、Meihua Xie

  DOI：10.1039/d0cc00300j

  日期：——

  The expeditious construction of phenanthridine scaffolds via a Pd/MnO2-mediated C-H arylation/oxidative annulation cascade involving aldehydes, aryl iodides and amino acids is disclosed. This reaction proceeds smoothly involving the formation of multiple chemical bonds with the tolerance of a wide range of functional groups. The control experiments suggest a radical mechanism for C-N bond formation

  公开了通过Pd / MnO 2介导的CH芳基化/氧化环化级联反应，涉及醛，芳基碘化物和氨基酸，快速构建菲啶支架。该反应顺利进行，涉及形成多个化学键，且具有宽泛的官能团耐受性。对照实验表明，通过MnO2促进亚胺化合物的氧化环化形成CN键的自由基机理。通过直接获得具有生物活性的天然生物碱三方酸及其类似物已证明了该转化的合成效用。
• 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。
• Synthesis of Phenanthridines through Iodine-Supported Intramolecular C–H Amination and Oxidation under Visible Light
  作者：Yan Gao、Yi Jing、Lixin Li、Jie Zhang、Xuenian Chen、Yan-Na Ma

  DOI：10.1021/acs.joc.0c01390

  日期：2020.10.2

  Herein, we report a metal-free and step-economic synthesis of phenanthridines from 2-biarylmethanamines under mild conditions. The reaction involves iodine-supported intramolecular C–H amination and oxidation of 5,6-dihydrophenanthridine under air and benign visible light. The mechanism study reveals that visible light plays a key role in both these steps.

  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。
• One‐pot Cascade Reaction for the Synthesis of Phenanthridines via Suzuki Coupling/C−H Oxidation/Aromatization
  作者：Yi Zhang、Yuxin Ding、Rener Chen、Yongmin Ma

  DOI：10.1002/adsc.202000949

  日期：2020.12.22

  A one‐pot cascade coupling/annulation reaction for the synthesis of phenanthridines has been developed from arylboronic acids and o‐bromo arylamides with DMSO as a carbon source. The desired phenanthridines were obtained in moderate to good yields by using simple procedure.

  由芳基硼酸和邻溴代芳基酰胺以DMSO为碳源开发了一种单锅级联偶联/环化反应，用于合成菲啶。通过使用简单的方法，以中等至良好的产率获得了所需的菲啶。
• One-Pot Palladium-Catalyzed Synthesis of Selectively Substituted Phenanthridines by Sequential Aryl-Aryl and Heck Couplings, Aza-Michael and Retro-Mannich Reactions
  作者：Nicola Della Ca'、Elena Motti、Antonio Mega、Marta Catellani

  DOI：10.1002/adsc.201000114

  日期：——

  A catalytic synthesis of selectively substituted phenanthridines is achieved through a reaction sequence involving palladium/norbornene‐catalyzed unsymmetrical aryl‐aryl and Heck couplings followed by aza‐Michael and retro‐Mannich reactions. In spite of the many steps involved the method is very simple and allows the formation of selectively substituted phenanthridines under mild conditions in a straightforward

  通过涉及钯/降冰片烯催化的不对称芳基-芳基和Heck偶联的反应序列，然后进行氮杂-迈克尔和逆曼尼希反应，可实现选择性取代的菲啶的催化合成。尽管涉及许多步骤，但该方法非常简单，并允许在温和条件下以简单易用的一锅反应从容易获得的芳基碘化物和溴化物开始形成选择性取代的菲啶。