4'-chloro-5-nitro<1,1'-biphenyl>-2-ol | 85841-96-9

• 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: 4'-chloro-5-nitro<1,1'-biphenyl>-2-ol
• 英文别名: 2-(4-chlorophenyl)-4-nitrophenol；4'-chloro-5-nitrobiphenyl-2-ol
• CAS: 85841-96-9
• 化学式: C₁₂H₈ClNO₃
• 分子量: 249.653
• InChiKey: DAQAFMKPVACEHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4'-chloro-5-nitro<1,1'-biphenyl>-2-ol 在 镍 氢气 、 三溴化硼 、 铜 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 4,4'''-dichloro<1,1':3',1'':3'',1'''-quaterphenyl>-4'',6'-diol
  参考文献：
  名称：

  Hung; Werbel, European Journal of Medicinal Chemistry, 1983, vol. 18, # 1, p. 61 - 66

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴-4-硝基苯甲醚 在 四(三苯基膦)钯 、 吡啶盐酸盐 作用下， 以 甲苯 为溶剂， 生成 4'-chloro-5-nitro<1,1'-biphenyl>-2-ol
  参考文献：
  名称：

  New non peptidic C5a receptor antagonists

  摘要：

  A series of phenylguanidines which bind to the C5a receptor has been developed. The lead compound 1 (IC50=30 mu M), discovered through random screening, has been modified to provide 32 (RPR121154) with submicromolar activity. This compound was shown to further elicit functional antagonism in a human neutrophil C5a stimulated respiratory burst assay. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00124-8

文献信息

• 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
  作者：Leslie M. Werbel、P. Dan Cook、Edward F. Elslager、Jocelyn H. Hung、Judith L. Johnson、Stephen J. Kesten、Dennis J. McNamara、Daniel F. Ortwine、Donald F. Worth

  DOI：10.1021/jm00156a009

  日期：1986.6

  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.
• Barlin, Gordon B.; Jiravinyu, Chuenjit, Australian Journal of Chemistry, 1990, vol. 43, # 7, p. 1301 - 1307
  作者：Barlin, Gordon B.、Jiravinyu, Chuenjit

  DOI：——

  日期：——
• CuI-Mediated Sequential Iodination/Cycloetherification of <i>o</i>-Arylphenols: Synthesis of 2- or 4-Iododibenzofurans and Mechanistic Studies
  作者：Jiaji Zhao、Qi Zhang、Lanying Liu、Yimiao He、Jing Li、Juan Li、Qiang Zhu

  DOI：10.1021/ol302562a

  日期：2012.10.19

  An efficient synthesis of 2- or 4-iododibenzofurans through Cul-mediated sequential iodination/cycloetherification of two aromatic C-H bonds in o-arylphenols has been developed. Both the preexisting electron-withdrawing groups (NO2, CN, and CHO) and the newly introduced iodide are readily modified for a focused dibenzofuran library synthesis. Mechanistic studies and DFT calculations suggest that a Cu(III)-mediated rate-limiting C-H activation step is involved in cycloetherification.
• Cu-Catalyzed Oxidative C(sp²)–H Cycloetherification of <i>o</i>-Arylphenols for the Preparation of Dibenzofurans
  作者：Jiaji Zhao、Yong Wang、Yimiao He、Lanying Liu、Qiang Zhu

  DOI：10.1021/ol203442a

  日期：2012.2.17

  A new process involving copper-catalyzed aerobic C(sp(2))-H activation, followed by cycloetherification, has been developed. This reaction serves as a direct method for the preparation of multisubstituted dibenzofurans starting with o-arylphenols. The presence of a strong para-electron-withdrawing group (e.g., NO2) on the phenol is essential for the success of the reaction.
• BARLIN, GORDON B.;JIRAVINYU, CHUENJIT, AUSTRAL. J. CHEM., 43,(1990) N, C. 1301-1307
  作者：BARLIN, GORDON B.、JIRAVINYU, CHUENJIT

  DOI：——

  日期：——