1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin | 439214-91-2

• 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: 1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin
• 英文别名: 1-(2,6-dichloro-phenyl)-3,4-dihydro-1H-quinazolin-2-one；1-(2,6-dichlorophenyl)-3,4-dihydroquinazolin-2(1H)-one；1-(2,6-dichlorophenyl)-3,4-dihydroquinazolin-2-one
• CAS: 439214-91-2
• 化学式: C₁₄H₁₀Cl₂N₂O
• 分子量: 293.152
• InChiKey: YHOHXMVUVUZHCI-UHFFFAOYSA-N

物化性质

• 沸点：
  490.5±45.0 °C(Predicted)
• 密度：
  1.409±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin 在 palladium on activated charcoal 硫酸 、 氢气 、 potassium nitrate 作用下， 以 乙醇 为溶剂， 反应 34.0h， 生成 6-Amino-1-(2,6-dichloro-phenyl)-3,4-dihydro-1H-quinazolin-2-one
  参考文献：
  名称：

  A novel Pd-catalyzed cyclization reaction of ureas for the synthesis of dihydroquinazolinone p38 kinase inhibitors

  摘要：

  A series of potent p38 inhibitors based on the dihydroquinazoline scaffold was synthesized using a novel Pd-catalyzed cyclization reaction of aryl-benzyl ureas. Optimization of this compound class led to compound 20, which inhibits p38alpha in vitro with IC50 = 14 nM and is active in the mouse TNFalpha-release model. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.006
• 作为产物：
  描述：

  双氯芬酸 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 以63%的产率得到1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin
  参考文献：
  名称：

  A novel Pd-catalyzed cyclization reaction of ureas for the synthesis of dihydroquinazolinone p38 kinase inhibitors

  摘要：

  A series of potent p38 inhibitors based on the dihydroquinazoline scaffold was synthesized using a novel Pd-catalyzed cyclization reaction of aryl-benzyl ureas. Optimization of this compound class led to compound 20, which inhibits p38alpha in vitro with IC50 = 14 nM and is active in the mouse TNFalpha-release model. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.006

文献信息

• A novel Pd-catalyzed cyclization reaction of ureas for the synthesis of dihydroquinazolinone p38 kinase inhibitors
  作者：Achim Schlapbach、Richard Heng、Franco Di Padova

  DOI：10.1016/j.bmcl.2003.11.006

  日期：2004.1

  A series of potent p38 inhibitors based on the dihydroquinazoline scaffold was synthesized using a novel Pd-catalyzed cyclization reaction of aryl-benzyl ureas. Optimization of this compound class led to compound 20, which inhibits p38alpha in vitro with IC50 = 14 nM and is active in the mouse TNFalpha-release model. (C) 2003 Elsevier Ltd. All rights reserved.