2,4-dichlorophenanthridine | 1360593-23-2

• 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: 2,4-dichlorophenanthridine
• CAS: 1360593-23-2
• 化学式: C₁₃H₇Cl₂N
• 分子量: 248.111
• InChiKey: ACDWAPQGEDWRNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2,4-dichloro-6-(furan-2-yl)aniline 在 盐酸 、 18-冠醚-6 、 氧气 、 potassium hydride 作用下， 以 水 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 3.42h， 生成 2,4-dichlorophenanthridine
  参考文献：
  名称：

  Synthesis of Phenanthridine Derivatives by Microwave-Mediated Cyclization of o-Furyl(allylamino)arenes

  摘要：

  A novel and efficient synthesis of phenanthridines and aza analogues is reported. The key step is a microwave-mediated intramolecular Diels-Alder cyclization of o-furyl(allylamino)arenes. In the presence of a catalytic amount of acid, the DA-adduct reacts further to give the dihydrophenanthridines, which easily can be oxidized to fully aromatic compounds by air in the presence of UV light or by DDQ.

  DOI：

  10.1021/jo3027033

文献信息

• Palladium-Catalyzed Oxidative CC Bond Cleavage Cyclization of Biaryl-2-amines with Alkenes Involving CH Olefination and Carboamination
  作者：Yan-Yun Liu、Ren-Jie Song、Cui-Yan Wu、Lu-Bin Gong、Ming Hu、Zhi-Qiang Wang、Ye-Xiang Xie、Jin-Heng Li

  DOI：10.1002/adsc.201100651

  日期：2012.2

  A new, general method for the synthesis of phenanthridines has been developed by palladium-catalyzed oxidative remote CH olefination–carboamination–CC bond cleavage tandem reaction. It is noteworthy that alkenes are used as the one-carbon resources for this tandem reaction.

  通过钯催化的氧化远程CH烯化反应-碳氨化反应-CC键裂解串联反应，开发了一种新型的菲啶合成方法。值得注意的是，烯烃被用作该串联反应的单碳资源。
• Formation of 8-Hydroxyphenanthridines by Microwave-Mediated IMDAF Reactions; Synthesis Directed towards Lycorine Alkaloids
  作者：Håkon Saetren Gulbrandsen、Halvard Serigstad、Matthew Lovell Read、Ilah Joos、Lise-Lotte Gundersen

  DOI：10.1002/ejoc.201901000

  日期：2019.9.22

  8‐Hydroxyphenathridines have been synthesized from N‐propargyl‐ortho‐furylanilines by a one‐pot intramolecular Diels–Alder reaction on furans (IMDAF) reaction and aromatization. N‐Propargyl‐7‐furylindol(in)es also underwent IMDAF cyclization to give (4,5‐dihydro)7H‐pyrrolo[3,2,1‐de]phenanthridin‐9‐ols These are structurally closely related to bioactive lycorine alkaloids.

  通过一锅内呋喃分子内Diels-Alder反应（IMDAF）和芳构化反应，由N-炔丙基-邻-呋喃基苯胺合成了8-羟基苯并吡啶。N-炔丙基-7-呋喃啉（in）也经历了IMDAF环化反应，得到（4,5-二氢）7 H-吡咯并[3,2,1- de ]菲啶-9-醇这些在结构上与生物活性的赖氨酸密切相关生物碱。