5-nitro-3'-(trifluoromethyl)<1,1'-biphenyl>-2-ol | 79287-44-8

• 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: 5-nitro-3'-(trifluoromethyl)<1,1'-biphenyl>-2-ol
• 英文别名: 5-nitro-3'-trifluoromethylbiphenyl-2-ol；4-Nitro-2-[3-(trifluoromethyl)phenyl]phenol
• CAS: 79287-44-8
• 化学式: C₁₃H₈F₃NO₃
• 分子量: 283.207
• InChiKey: DPQICEOQLZNIGL-UHFFFAOYSA-N

物化性质

• 熔点：
  185-187 °C
• 沸点：
  389.0±42.0 °C(Predicted)
• 密度：
  1.426±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-nitro-3'-(trifluoromethyl)<1,1'-biphenyl>-2-ol 在 镍 氨 、 氢气 作用下， 以 乙醇 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Barlin, Gordon B.; Tian, Fu-Li; Kotecka, Barbara, Australian Journal of Chemistry, 1992, vol. 45, # 11, p. 1845 - 1855

  摘要：

  DOI：
• 作为产物：
  描述：

  3-三氟甲基苯丙酮 、 sodium nitromalonaldehyde 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以60%的产率得到5-nitro-3'-(trifluoromethyl)<1,1'-biphenyl>-2-ol
  参考文献：
  名称：

  Antimalarial drugs. 60. Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N.omega.-oxides

  摘要：

  A series of 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl] [1,1'-biphenyl]-2-ols and N omega-oxides was prepared from the substituted 1-phenyl-2-propanones proceeding through the 5-nitro[1,1'-biphenyl]-2-ols, the corresponding amino, and acetamido derivatives to the N-[5-[(alkylamino)methyl]-6-hydroxy[1,1'-biphenyl]-3-yl]acetamides and final condensation with 4,7-dichloroquinoline or the N-oxide. In a quantitative structure-activity relationship study first run on 28 and later expanded to 40 substituted phenyl analogues and their N omega-oxides, increasing antimalarial potency vs. Plasmodium berghei in mice was found to be correlated with decreasing size (sigma MR) and electron donation (sigma sigma) of the phenyl ring substituents. A significant correlation with N omega-oxidation could not be demonstrated. Initial high activity against P. berghei infections in mice led to expanded studies that demonstrated in addition excellent activity against resistant strains of parasite, activity in primate models, and pharmacokinetic properties apparently allowing protection against infection for extended periods of time even after oral administration. Such properties encourage the clinical trial of a member of this class in man.

  DOI：

  10.1021/jm00156a009

文献信息

• WERBEL L. M.; COOK P. D.; ELSLAGER E. F.; HUNG J. H.; JOHNSON J. L.; KEST+, J. MED. CHEM., 29,(1986) N 6, 924-939
  作者：WERBEL L. M.、 COOK P. D.、 ELSLAGER E. F.、 HUNG J. H.、 JOHNSON J. L.、 KEST+

  DOI：——

  日期：——