2-(4-甲基苯基)吡啶-3-醇 | 36739-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-(4-甲基苯基)吡啶-3-醇
• 英文名称: 2-(p-tolyl)pyridin-3-ol
• 英文别名: 2-(4-Methylphenyl)pyridin-3-ol
• CAS: 36739-30-7
• 化学式: C₁₂H₁₁NO
• mdl: MFCD00466480
• 分子量: 185.225
• InChiKey: MFAQZCMCEFTNIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  199-200 °C
• 沸点：
  383.3±27.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-甲基苯基)吡啶-3-醇 在 叔丁基锂 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 、 正戊烷 为溶剂， 反应 1.16h， 生成 3-(2-p-tolylpyridin-3-yl)phenol
  参考文献：
  名称：

  重复两步法合成低聚芳烃的Negishi偶联策略

  摘要：

  开发了一种新颖的重复性两步法合成低聚芳烃的方法，该方法基于Negishi将氧化锌苯酚或氧化锌吡啶氧化物与芳基三氟甲磺酸酯交叉偶联，然后对羟基进行三氟甲磺酸酯化。优化了反应条件以制备芳基锌化合物和钯催化的交叉偶联步骤。

  DOI：

  10.1016/j.tetlet.2006.06.048
• 作为产物：
  描述：

  2-(4-甲基苯基)吡啶 在 Escherichia coli with modified biphenyl dioxygenase genes 作用下， 以 乙醇 为溶剂， 以9.0 mg的产率得到2-(4-甲基苯基)吡啶-3-醇
  参考文献：
  名称：

  Hydroxylation of various molecules including heterocyclic aromatics using recombinant Escherichia coli cells expressing modified biphenyl dioxygenase genes

  摘要：

  Various molecules, in which heterocyclic aromatics are linked with phenyl or benzyl groups, were converted to their corresponding cis-dihydrodiols by recombinant Escherichia coli cells expressing modified biphenyl dioxygenase genes. Heterocyclic aromatic compounds with substituted phenyl or aliphatic moieties were also biotransformed to the hydroxylated products by the cells. Many of the converted products were novel compounds. These compounds are potentially useful as versatile starting materials for the chemical synthesis of pharmaceuticals and biologically active organic molecules. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01253-x

文献信息

• Frozen aryldiazonium chlorides in radical reactions with alkenes and arenes
  作者：Daniel Thon、Michael C.D. Fürst、Lisa-Marie Altmann、Markus R. Heinrich

  DOI：10.1016/j.tet.2018.05.089

  日期：2018.9

  Frozen aryldiazonium chlorides have been investigated in radical alkene and arene functionalizations. Through freezing at – 84 °C, aryldiazonium chlorides, which otherwise show significant decomposition in aqueous solution after several hours at room temperature, can be stored for at least 20 days. In addition, the slow melting of aryldiazonium-containing ice cubes can serve as an alternative to syringe

  已经在自由基烯烃和芳烃官能化中研究了冷冻的芳基重氮氯化物。通过在– 84°C下冷冻，芳基重氮氯化物在室温下几个小时后会在水溶液中显着分解，因此可以储存至少20天。另外，如果需要将重氮盐受控地添加到反应混合物中，则含芳基重氮鎓的冰块的缓慢熔化可以代替通常使用的注射泵。
• Regioselective Radical Arylation of 3-Hydroxypyridines
  作者：Michael C. D. Fürst、Leonard R. Bock、Markus R. Heinrich

  DOI：10.1021/acs.joc.6b00894

  日期：2016.7.1

  The titanium(III)-mediated radical arylation of 3-hydroxypyridines was found to proceed with high regioselectivity for the 2-position. Using aryldiazonium chlorides, which were prepared from the corresponding anilines, as aryl radical sources, a range of 3-hydroxy-2-phenylpyridines were obtained in moderate to good yields under simple reaction conditions. Reactions of ortho-carboxylic ester substituted

  发现3-羟基吡啶的钛（III）介导的自由基芳基化以对2-位的高区域选择性进行。使用由相应的苯胺制备的芳基重氮氯化物作为芳基自由基源，在简单的反应条件下以中等至良好的收率获得了一系列的3-羟基-2-苯基吡啶。邻羧酸酯取代的苯基重氮盐的反应直接提供了三环苯并吡喃并吡啶并酮。
• Iridium-Catalyzed Selective Hydrogenation of 3-Hydroxypyridinium Salts: A Facile Synthesis of Piperidin-3-ones
  作者：Wen-Xue Huang、Bo Wu、Xiang Gao、Mu-Wang Chen、Baomin Wang、Yong-Gui Zhou

  DOI：10.1021/acs.orglett.5b00276

  日期：2015.4.3

  homogeneous iridium catalyst, providing a direct access to 2- and 4-substituted piperidin-3-one derivatives with high yields, which are important organic synthetic intermediates and the prevalent structural motifs in pharmaceutical agents. Mild reaction conditions, high chemoselectivity, and easy scalability make this reaction highly practical for the synthesis of piperidin-3-ones.

  已经使用均相铱催化剂实现了3-羟基吡啶鎓盐的选择性加氢，可以高产率直接获得2-和4-取代的哌啶-3-酮衍生物，这些衍生物是重要的有机合成中间体，并且在结构上很普遍。药剂。温和的反应条件，高的化学选择性和容易的可扩展性使该反应在合成哌啶3-3-酮中具有很高的实用性。
• Design, Synthesis, and Biological Evaluation of Novel 2‐(Pyridin‐3‐yloxy)acetamide Derivatives as Potential Anti‐ <scp>HIV</scp> ‐1 Agents
  作者：Boshi Huang、Xiao Li、Peng Zhan、Erik De Clercq、Dirk Daelemans、Christophe Pannecouque、Xinyong Liu

  DOI：10.1111/cbdd.12657

  日期：2016.2

  Through a structure‐based molecular hybridization and bioisosterism approach, a series of novel 2‐(pyridin‐3‐yloxy)acetamide derivatives were designed, synthesized, and evaluated for their anti‐HIV activities in MT‐4 cell cultures. Biological results showed that three compounds (Ia, Ih, and Ij) exhibited moderate inhibitory activities against wild‐type (wt) HIV‐1 strain (IIIB) with EC50 values ranging

  通过基于结构的分子杂交和生物立体异构方法，设计，合成了一系列新颖的2-（吡啶-3-基氧基）乙酰胺衍生物，并评估了它们在MT-4细胞培养物中的抗HIV活性。生物结果表明，三种化合物（IA，小时，和IJ）显示出对野生型（wt）HIV-1毒株（III中等抑制活性乙）与EC 50个值范围为8.18 μ米到41.52 μ米。其中，IJ是最活跃的类似物具有的EC 50的值8.18 μ米。为了进一步确定结合靶标，选择了四种化合物来进行HIV-1 RT抑制测定。此外，还详细讨论了三种活性化合物Ia，Ih和Ij的初步结构-活性关系（SAR）分析和一些预测的理化性质。还进行了分子对接研究，以研究Ij和先导化合物GW678248在RT的结合口袋中的结合方式，这为进一步合理设计非核苷类逆转录酶抑制剂提供了有益的信息。
• Method for producing a heterocyclic compound and an aromatic carboxylic acid having one or more hydroxyl groups, and modified aromatic ring dioxygenase
  申请人：——

  公开号：US20040086983A1

  公开（公告）日：2004-05-06

  An objective of the present invention is to provide a method of producing hydroxylated heterocyclic compounds and hydroxylated aromatic carboxylic acids by bioengineering technique, and modified enzymes which can be used for this method. A method of producing hydroxylated heterocyclic compounds or hydroxylated aromatic carboxylic acids comprises reacting an aromatic ring dioxygenase with heterocyclic compounds or aromatic carboxylic acids to hydroxylate these compounds. An enzyme according to the present invention is an aromatic ring dioxygenase comprising an &agr;-subunit consisting of the amino acid sequence of SEQ ID NO: 2, which is modified according to the &agr;-subunit of the biphenyl dioxygenase derived from the strain Burkholderia cepacia LB400, a &bgr;-subunit consisting of the amino acid sequence of SEQ ID NO: 4, and a ferredoxin consisting of the amino acid sequence of SEQ ID NO: 6, and a ferredoxin reductase consisting of the amino acid sequence of SEQ ID NO: 8.

  本发明的目的是提供一种通过生物工程技术生产羟基化杂环化合物和羟基化芳香族羧酸的方法，以及可用于该方法的改良酶。生产羟基化杂环化合物或羟基化芳香族羧酸的方法包括使芳香环二加氧酶与杂环化合物或芳香族羧酸反应，使这些化合物羟基化。根据本发明的一种酶是一种芳香环二加氧酶，它包括一个由 SEQ ID NO: 2 的氨基酸序列组成的&agr;-亚基，它是根据从菌株中得到的联苯二加氧酶的&agr;-亚基修饰的 伯克霍尔德氏菌 LB400，由 SEQ ID NO: 4 的氨基酸序列组成的&bgr;-亚基，由 SEQ ID NO: 6 的氨基酸序列组成的铁毒素，以及由 SEQ ID NO: 8 的氨基酸序列组成的铁毒素还原酶。