7-methoxyphenanthridine | 1194718-79-0

• 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-methoxyphenanthridine
• CAS: 1194718-79-0
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: IDRPYCHAADIKOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  22.12
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2'-bromo-3-methoxy-[1,1'-biphenyl]-2-carbonitrile 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以79%的产率得到7-methoxyphenanthridine
  参考文献：
  名称：

  Hydride-Induced Anionic Cyclization: An Efficient Method for the Synthesis of 6-H-Phenanthridines via a Transition-Metal-Free Process

  摘要：

  A novel procedure for hydride-induced anionic cyclization has been developed. It includes the reduction of a biaryl bromo-nitrile with a nucleophilic aromatic substitution (SNAr). A range of polysubstituted 6-H-phenanthridines were so obtained in moderate to good yield with good substrate tolerance. This method involves a concise transition-metal-free process and was applied to synthesize natural alkaloids.

  DOI：

  10.1021/acs.orglett.5b00544

文献信息

• A new synthetic approach to 6-unsubstituted phenanthridine and phenanthridine-like compounds under mild and metal-free conditions
  作者：Jumreang Tummatorn、Suppachai Krajangsri、Krissada Norseeda、Charnsak Thongsornkleeb、Somsak Ruchirawat

  DOI：10.1039/c4ob00797b

  日期：——

  A new and mild synthetic approach for the synthesis of 6-unsubstituted phenanthridine and phenanthridine-like compounds under metal-free conditions at room temperature has been developed. The strategy involved a tandem azide rearrangement/intramolecular annulation and oxidation reactions of biarylmethyl azide precursors to obtain the desired products in up to 99% yields with high regioselectivity.

  在室温下于无金属条件下，开发了一种用于合成6-未取代菲啶及其类似化合物的新型温和合成方法。该策略涉及二芳基甲基叠氮前体的串联叠氮重排/分子内环化及氧化反应，以高达99%的产率和高区域选择性获得目标产物。
• 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。
• Metal-free tandem carbene N–H insertions and C–C bond cleavages
  作者：Pu Chen、Jiang Nan、Yan Hu、Yifan Kang、Bo Wang、Yangmin Ma、Michal Szostak

  DOI：10.1039/d0sc05763k

  日期：——

  with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C–C cleavage. Compared to the simple N–H insertion manipulation of diazo, this method elegantly accomplishes a tandem N–H insertion/SEAr/C–C cleavage/aromatization reaction, and the synthetic utility of this new transformation is exemplified by the succinct syntheses of trisphaeridine and

  已经实现了 2-芳基苯胺与重氮化合物的无金属 C-H [5 + 1] 环化反应，通过高度选择性的 C-C 裂解产生两种普遍的菲啶。与重氮的简单 N-H 插入操作相比，该方法优雅地完成了串联 N-H 插入/S E Ar/C-C 裂解/芳构化反应，这种新转化的合成效用通过简洁的合成trisphaeridine 和 bicolorine 生物碱。