6-bromo-N-butyl-N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]benzo[d][1,3]dioxole-5-carboxamide | 1307741-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-bromo-N-butyl-N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]benzo[d][1,3]dioxole-5-carboxamide
• CAS: 1307741-67-8
• 化学式: C₂₁H₁₈BrF₆NO₄
• 分子量: 542.273
• InChiKey: WIZHZCGGERUQES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-bromo-N-butyl-N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]benzo[d][1,3]dioxole-5-carboxamide 在 palladium diacetate 、 caesium carbonate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 2,4-滴二甲胺盐 为溶剂， 反应 3.0h， 以78%的产率得到5-butyl-2-(1',1',1',3',3',3'-hexafluoro-2'-hydroxypropan-2'-yl)-[1,3] dioxolo[4,5-j] phenanthridin-6(5H)-one
  参考文献：
  名称：

  Fused heterocyclic amido compounds as anti-hepatitis C virus agents

  摘要：

  We identified a fused heteroaromatic amido structure based on the phenanthridine skeleton as a superior scaffold for candidate drugs with potent anti-HCV activity. Among the compounds synthesized, a phenanthridine analogue with a 1,3-dioxolyl group (24) possessed the most potent anti-HCV activity (EC50 value: 50 nM), with acceptable cytotoxicity. The structural development and structure-activity relationships of these compounds are described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.002
• 作为产物：
  描述：

  2-(4-(butylamino)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol 、 6-溴苯并[d][1,3]二氧代-5-羧酸 在 (氯亚甲基)二甲基氯化铵 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以80%的产率得到6-bromo-N-butyl-N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]benzo[d][1,3]dioxole-5-carboxamide
  参考文献：
  名称：

  Fused heterocyclic amido compounds as anti-hepatitis C virus agents

  摘要：

  We identified a fused heteroaromatic amido structure based on the phenanthridine skeleton as a superior scaffold for candidate drugs with potent anti-HCV activity. Among the compounds synthesized, a phenanthridine analogue with a 1,3-dioxolyl group (24) possessed the most potent anti-HCV activity (EC50 value: 50 nM), with acceptable cytotoxicity. The structural development and structure-activity relationships of these compounds are described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.002