9-methoxy-6-phenylphenanthridine | 98352-00-2

• 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: 9-methoxy-6-phenylphenanthridine
• CAS: 98352-00-2
• 化学式: C₂₀H₁₅NO
• 分子量: 285.345
• InChiKey: CCKAXGQRLIDSCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3'-甲氧基-2-联苯胺 在 过氧化二碳酸二异丙酯 作用下， 以 乙醇 、 苯 为溶剂， 反应 4.08h， 生成 9-methoxy-6-phenylphenanthridine
  参考文献：
  名称：

  A New and Convenient Synthesis of Phenanthridines

  摘要：

  DOI：

  10.1055/s-1985-31129

文献信息

• Mo–Catalyzed One‐Pot Synthesis of <i>N</i> ‐Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent‐Tuned Photophysical Properties
  作者：Raquel Hernández‐Ruiz、Rubén Rubio‐Presa、Samuel Suárez‐Pantiga、María R. Pedrosa、Manuel A. Fernández‐Rodríguez、M. José Tapia、Roberto Sanz

  DOI：10.1002/chem.202102000

  日期：2021.9.24

  reduction–imine formation–intramolecular cyclization–oxidation for the general synthesis of a wide variety of biologically relevant N-polyheterocycles, such as quinoxaline- and quinoline-fused derivatives, and phenanthridines, is reported. A simple, easily available, and environmentally friendly dioxomolybdenum(VI) complex has proven to be a highly efficient and versatile catalyst for transforming a

  据报道，催化多米诺还原-亚胺形成-分子内环化-氧化用于一般合成各种生物学相关的N-多杂环，例如喹喔啉和喹啉稠合衍生物以及菲啶。一种简单、易得且环保的二氧代钼(VI)络合物已被证明是一种高效且多功能的催化剂，可用于转化涉及多种氧化还原过程的各种起始硝基芳烃。这不仅是一种可持续、步骤经济且耐空气和耐湿的方法，而且值得强调的是，序列第一步中产生的废物副产物被回收并合并到最终的目标分子中，从而改善了整体合成效率。此外，选定的吲哚喹喔啉在环己烷和甲苯中进行了光物理表征，烷基衍生物的荧光量子产率高于 0.7。
• Base‐Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines
  作者：Debabrata Maiti、Atreyee Halder、Suman De Sarkar

  DOI：10.1002/adsc.201900995

  日期：2019.11.5

  transition metal‐free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2‐iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C−N bond formation followed by a radical C−C coupling in a cascade sequence. The used base potassium tert‐butoxide plays a dual role in dehydrogenation

  目前的方案代表了从苯甲醛和2-碘苯胺衍生物等丰富的原料中无过渡金属合成多取代菲啶的方法。该反应涉及依次进行的醇氧化和与胺的直接缩合反应，形成C-N键，然后以级联顺序进行自由基C-C偶联。使用的碱式叔丁醇钾在脱氢和均相芳族取代反应中起双重作用。使用这种方法，合成了二十种取代的菲啶衍生物，分离产率高达85％。
• Near-IR two-photon absorption photostabilizers for polymers intensified by molecular assembly in mixed organic solvents/H2O
  作者：Yueting Shi、Xiaozhuan Qin、Gang Li、Hongru Li、Ge Ding、Xiaohong Liu、Fang Gao

  DOI：10.1016/j.molliq.2021.117590

  日期：2021.12

  phenanthridine dyes carrying hydroxy groups that were employed as near-IR two-photon absorption (TPA) photostabilizers for polymers. It was demonstrated that the target phenanthridine dyes underwent reversible excited state proton transfer (ESPT) in strong polar protic and aprotic solvents, such as ethanol, which was more remarkable under near-IR two-photon excitation. It was determined that the target dyes

  该研究报告了各种带有羟基的目标菲啶染料，这些染料被用作聚合物的近红外双光子吸收 (TPA) 光稳定剂。结果表明，目标菲啶染料在强极性质子和非质子溶剂（如乙醇）中经历了可逆激发态质子转移（ESPT），这在近红外双光子激发下更为显着。确定目标染料在混合有机溶剂/H 2 O 溶剂（如乙醇/H 2O，90% 的水体积）。目标菲啶染料的有序分子聚集分别增强了单光子和近红外双光子激发下的可逆 ESPT 发射。因此，目标染料的可逆 ESPT 过程消耗了吸收的能量。因此，目标染料被评估为聚合物的近红外 TPA 光稳定剂。相比之下，缺乏羟基的参考菲啶染料在光照射下没有表现出 ESPT 或光稳定性。
• Trifluoroacetic acid-mediated facile construction of 6-substituted phenanthridines
  作者：So Won Youn、Joon Hyung Bihn

  DOI：10.1016/j.tetlet.2009.05.071

  日期：2009.8

  The trifluoroacetic acid-mediated reaction of 2-arylanilines with arylaldehydes has been developed to give a variety of 6-substituted phenanthridines. This is a very simple and convenient one-pot process for library construction. (C) 2009 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Intramolecular C–H Activation/C–C Bond Formation: A Straightforward Synthesis of Phenanthridines
  作者：Jinsong Peng、Tonghui Chen、Chunxia Chen、Bin Li

  DOI：10.1021/jo2017108

  日期：2011.11.18

  The palladium-catalyzed intramolecular C-H activation/C-C cross-coupling has been developed for a straightforward and efficient synthesis of phenanthridines. With Pd(OAc)(2) (4 mol %) as the catalyst, PCy3 (8 mol %) as the ligand, and Cs2CO3 as the base, this protocol was applied to synthesize a small library of phenanthridine derivatives in good yields in THF.