2,4-dichloro-5,6-dihydrophenanthridine | 1421503-90-3

• 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-dichloro-5,6-dihydrophenanthridine
• 英文别名: 2,4-Dichloro-5,6-dihydrophenanthridine
• CAS: 1421503-90-3
• 化学式: C₁₃H₉Cl₂N
• 分子量: 250.127
• InChiKey: BNZMOFRNWUVDJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-5,6-dihydrophenanthridine 在 氧气 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 以88 mg的产率得到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
• 作为产物：
  描述：

  2-溴-4,6-二氯苯胺 在 盐酸 、 18-冠醚-6 、 palladium diacetate 、 potassium hydride 、 potassium carbonate 、 三苯基膦 作用下， 以 乙醇 、 水 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 6.17h， 生成 2,4-dichloro-5,6-dihydrophenanthridine
  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

• 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。
• Synthesis of Phenanthridine Derivatives by Microwave-Mediated Cyclization of <i>o</i>-Furyl(allylamino)arenes
  作者：Matthew Lovell Read、Lise-Lotte Gundersen

  DOI：10.1021/jo3027033

  日期：2013.2.1

  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.