2-(2-(allyloxy)-3-chlorophenyl)furan | 1421504-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-(allyloxy)-3-chlorophenyl)furan
• 英文别名: 2-(3-Chloro-2-prop-2-enoxyphenyl)furan；2-(3-chloro-2-prop-2-enoxyphenyl)furan
• CAS: 1421504-03-1
• 化学式: C₁₃H₁₁ClO₂
• 分子量: 234.682
• InChiKey: ITPWHHINEKXPDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-(allyloxy)-3-chlorophenyl)furan 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以39%的产率得到4-chloro-6H-benzo[c]chromene
  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：

  3-氯-2-氟溴苯 在 bis-triphenylphosphine-palladium(II) chloride 、 15-冠醚-5 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 21.17h， 生成 2-(2-(allyloxy)-3-chlorophenyl)furan
  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.