2,3-dimethoxylphenanthridine

• 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: 2,3-dimethoxylphenanthridine
• 英文别名: 2,3-dimethoxyphenanthridine
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: PEMVRIBFMNATQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  trimethyl(2-nitro-4,5-dimethoxyphenyl)stannane 在 四(三苯基膦)钯 、 溶剂黄146 、 copper(I) bromide 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 2,3-dimethoxylphenanthridine
  参考文献：
  名称：

  硝基芳基锡烷类作为合成子，用于制备菲啶和苯并[i]菲啶衍生物。

  摘要：

  DOI：

  10.1021/jo991318g

文献信息

• Metal-Free Photoredox Catalyzed Cyclization of O-(2,4-Dinitrophenyl)oximes to Phenanthridines
  作者：Xiubin Liu、Zhixing Qing、Pi Cheng、Xinyu Zheng、Jianguo Zeng、Hongqi Xie

  DOI：10.3390/molecules21121690

  日期：——

  A metal-free visible-light photoredox-catalyzed intermolecular cyclization reaction of O-2,4-dinitrophenyl oximes to phenanthridines was developed. In this study, the organic dye eosin Y and i-Pr₂NEt were used as photocatalyst and terminal reductant, respectively. The oxime substrates were transformed into iminyl radical intermediates by single-electron reduction, which then underwent intermolecular

  开发了一种无金属的可见光光氧化还原催化的O-2,4-二硝基苯基肟与菲啶的分子间环化反应。在这项研究中，有机染料曙红Y和i-Pr 2 NEt分别用作光催化剂和末端还原剂。通过单电子还原将肟底物转化为亚氨基自由基中间体，然后使其进行分子间均溶芳族取代（HAS）反应，得到菲啶衍生物。
• Synthesis of Phenanthridines and Analogues via Suzuki Coupling and Condensation
  作者：Jayanta Ray、Shubhendu Dhara、Munmun Ghosh

  DOI：10.1055/s-0033-1339793

  日期：——

  A convenient and short methodology has been developed towards the synthesis of highly substituted phenanthridines and their analogous benzo[k] and benzo[i] derivatives in a single step via Suzuki coupling and condensation between suitably substituted aromatic ortho-bromoaldehydes and ortho-aminobenzeneboronic acids in good to excellent yields.

  已开发出一种方便且简短的方法，通过适当取代的芳香族邻溴醛和邻氨基苯硼酸之间的 Suzuki 偶联和缩合，一步合成高度取代的菲啶及其类似的苯并 [k] 和苯并 [i] 衍生物。良好的产量。
• Hydride-Induced Anionic Cyclization: An Efficient Method for the Synthesis of 6-<i>H</i>-Phenanthridines via a Transition-Metal-Free Process
  作者：Wei-Lin Chen、Chun-Yuan Chen、Yan-Fu Chen、Jen-Chieh Hsieh

  DOI：10.1021/acs.orglett.5b00544

  日期：2015.3.20

  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.