3-chloro-5,6-dihydrobenzo[c][1,5]naphthyridine | 1421503-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-chloro-5,6-dihydrobenzo[c][1,5]naphthyridine
• 英文别名: 3-Chloro-5,6-dihydrobenzo[c][1,5]naphthyridine
• CAS: 1421503-94-7
• 化学式: C₁₂H₉ClN₂
• 分子量: 216.67
• InChiKey: DEFGUHWKYDEFHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 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：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-5,6-dihydrobenzo[c][1,5]naphthyridine 在 氧气 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以70 mg的产率得到3-chlorobenzo[c][1,5]naphthyridine
  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-3-氨基-5-氯吡啶 在 盐酸 、 15-冠醚-5 、 palladium diacetate 、 sodium 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 26.17h， 生成 3-chloro-5,6-dihydrobenzo[c][1,5]naphthyridine
  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

• 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.