4-chloro-2'-hydroxybiphenyl | 64181-76-6

• 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-2'-hydroxybiphenyl
• 英文别名: 4'-chlorobiphenyl-2-ol；2-(4-chlorophenyl)phenol；4'-chloro-[1,1'-biphenyl]-2-ol；2'-hydroxy-4-chlorobiphenyl；4'-Chlor-2-hydroxy-biphenyl
• CAS: 64181-76-6
• 化学式: C₁₂H₉ClO
• 分子量: 204.656
• InChiKey: DSSULPPMTATCMP-UHFFFAOYSA-N

物化性质

• 保留指数：
  1680

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-chloro-2'-hydroxybiphenyl 在 sodium dithionite 、 水 、 sodium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 5.0h， 生成 N-[5-(sec-Butylamino-methyl)-4'-chloro-6-hydroxy-biphenyl-3-yl]-acetamide
  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
• 作为产物：
  描述：

  6-(4-chlorophenyl)-2-cyclohexen-1-one 在 氢溴酸 、 碘 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 生成 4-chloro-2'-hydroxybiphenyl
  参考文献：
  名称：

  非甾体抗炎药。3. 4'-氯-5-甲氧基-3-联苯基乙酸的位置异构体的合成及其抗炎和镇痛活性。

  摘要：

  4'-氯-5-甲氧基-3-联苯基乙酸的位置异构体3a-i [1（DKA-9），R = 4-ClPh; R'= MeO]是一种新开发的非甾体类抗炎药，已使用角叉菜胶诱导的大鼠爪水肿和AcOH扭体试验进行了抗炎和镇痛作用的评估。在这些测定中，与其他异构体相比，在结构上非常相似于1（R = 4-ClPh，R'= MeO）的3-和4-联苯基乙酸3a，d。但是，所测试的化合物均没有一个比1更具活性（R = 4-ClPh； R'= MeO）。在这一系列化合物中，良好的抗炎活性的结构要求似乎与镇痛活性的要求平行。

  DOI：

  10.1021/jm00140a019

文献信息

• 3-Hydroxypyrimidine-2,4-diones as Selective Active Site Inhibitors of HIV Reverse Transcriptase-Associated RNase H: Design, Synthesis, and Biochemical Evaluations
  作者：Jing Tang、Feng Liu、Eva Nagy、Lena Miller、Karen A. Kirby、Daniel J. Wilson、Bulan Wu、Stefan G. Sarafianos、Michael A. Parniak、Zhengqiang Wang

  DOI：10.1021/acs.jmedchem.5b01879

  日期：2016.3.24

  achieve selective RNase H inhibition. Biochemical studies showed the two subtypes with an N-1 methyl group (9 and 10) inhibited RNase H in low micromolar range without siginificantly inhibiting RT polymerase, whereas the N-1 unsubstituted subtype 11 inhibited RNase H in submicromolar range and RT polymerase in low micromolar range. Subtype 11 also exhibited substantially reduced inhibition in the HIV-1

  人类免疫缺陷病毒（HIV）逆转录酶（RT）相关的核糖核酸酶H（RNase H）仍然是未经验证的抗病毒靶标。特异性靶向HIV RNase H的主要挑战来自对RT聚合酶（pol）和整合酶（IN）链转移（ST）抑制作用的普遍缺乏选择性。我们在此报告了三种新颖的3-羟基嘧啶-2,4-二酮（HPD）亚型的合成和生化评估，这些亚型经过精心设计以实现选择性RNase H抑制。生化研究表明，具有N-1甲基的两个亚型（9和10）在低微摩尔范围内抑制RNase H，而未显着抑制RT聚合酶，而N-1未取代的亚型11在亚微摩尔范围内抑制RNase H，在低微摩尔范围内抑制RT聚合酶。亚型11在HIV-1 INST分析中也表现出明显降低的抑制作用，在细胞生存力分析中没有明显的细胞毒性，这表明它可能适合进一步的结构-活性关系（SAR），以鉴定具有抗病毒活性的RNase H抑制剂。
• Sustainable H2O/ethyl lactate system for ligand-free Suzuki–Miyaura reaction
  作者：Jie-Ping Wan、Chunping Wang、Rihui Zhou、Yunyun Liu

  DOI：10.1039/c2ra21632a

  日期：——

  A sustainable catalyst system consisted of H2O/ethyl lactate (EL), Pd(OAc)2 and K2CO3 has been developed as a generally applicable protocol for Suzuki–Miyaura reactions using various aryl bromides and iodides to incorporate arylboronic acids under ligand-free conditions. This protocol is advantageous owing to the employment of water and non-toxic, biomass available ethyl lactate as green media. In addition, as a co-solvent with water, ethyl lactate displayed evident superiority over conventional polar organic solvents such as DMF, DMSO and dioxane etc., which implied the additional potential function of EL as a ligand in these reactions.

  开发了一种可持续的催化体系，由H2O/乳酸乙酯（EL）、Pd(OAc)2和K2CO3组成，作为一种普遍适用的方案，用于在无配体条件下使用各种芳基溴和碘化物进行铃木-宫浦反应，以引入芳基硼酸。这一方案具有优势，因为它采用了水和无毒、可从生物质中获得的乳酸乙酯作为绿色溶剂。此外，作为水的共溶剂，乳酸乙酯在性能上明显优于传统极性有机溶剂，如DMF、DMSO和二氧六环等，这意味着EL在这些反应中还具有额外的潜在配体功能。
• Strongly Directing Substituents in the Radical Arylation of Substituted Benzenes
  作者：Josefa Hofmann、Timothy Clark、Markus R. Heinrich

  DOI：10.1021/acs.joc.6b01840

  日期：2016.10.21

  radical arylation reactions has grown rapidly in recent years, poor regioselectivities and the need to use a large excess of the radical-accepting arene have hindered their application to substituted benzenes. We now describe experimental and computational investigations into the substituent effects that lead to regioselective addition based on the recent discovery of anilines as outstanding substrates

  尽管近年来人们对自由基芳基化反应的普遍兴趣迅速增长，但区域选择性差，以及需要使用大量过量的能接受自由基的芳烃阻碍了它们在取代苯中的应用。现在我们基于对苯胺作为自由基芳基化的杰出底物的最新发现，描述对导致区域选择性加成的取代基效应的实验和计算研究。
• Regioselective Radical Arylation of Anilines with Arylhydrazines
  作者：Hannelore Jasch、Julia Scheumann、Markus R. Heinrich

  DOI：10.1021/jo301980j

  日期：2012.12.7

  arylhydrazines and anilines via radical arylation reactions under simple oxidative conditions. The strong directing effect of the free and unprotonated amino functionality leads to high regioselectivities, and anilines have been shown to be significantly better aryl radical acceptors than nitrobenzenes or phenyl ethers. The methodology is also applicable to phenols, which react best as phenolates under

  取代的2-氨基联苯已由芳基肼和苯胺在简单的氧化条件下通过自由基芳基化反应制得。游离的和未质子化的氨基官能团的强引导作用导致高的区域选择性，并且苯胺已被证明是比硝基苯或苯基醚更好的芳基自由基受体。该方法还适用于在强碱性条件下以酚盐形式反应最好的酚。最后，苯胺和苯胺盐在各种条件下的自由基芳基化反应首次证明，还可以通过重新芳构化步骤来控制区域选择性，并且向取代的苯中添加芳基甚至是可逆的。
• Palladium-catalyzed direct arylation of phenols with aryl iodides
  作者：Rongrong Long、Xufei Yan、Zhiqing Wu、Zhengkai Li、Haifeng Xiang、Xiangge Zhou

  DOI：10.1039/c5ob00132c

  日期：——

  An efficient protocol of palladium-catalyzed direct para-arylation of unfunctionalized phenols with aryl iodides under mild conditions was reported.

  一种高效的钯催化直接对未官能化酚进行芳基碘化的方法在温和条件下被报道。