2-(2-hydroxy-5-nitrophenyl)pyridine | 33400-82-7

• 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
• 英文名称: 2-(2-hydroxy-5-nitrophenyl)pyridine
• 英文别名: 4-nitro-2-(pyridin-2-yl)phenol；4-Nitro-2-pyridin-2-ylphenol
• CAS: 33400-82-7
• 化学式: C₁₁H₈N₂O₃
• mdl: MFCD00483296
• 分子量: 216.196
• InChiKey: JZTWSPJNEZBBNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 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：
  78.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxy-5-nitrophenyl)pyridine 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-(2-Mercapto-5-nitrophenyl)pyridine
  参考文献：
  名称：

  Abramovitch, Rudolph A.; Inbasekaran, Muthiah N.; Miller, Adrian L., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 509 - 512

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-甲氧基苯基)吡啶 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.83h， 生成 2-(2-hydroxy-5-nitrophenyl)pyridine
  参考文献：
  名称：

  Tautomers of azine derivatives. 21. Tautomerism in 2-(2-hydroxyaryl)azines

  摘要：

  DOI：

  10.1007/bf00506851

文献信息

• Squaric Acid Derivatives as Protein Kinase Inhibitors
  申请人：Mederski Werner

  公开号：US20080312244A1

  公开（公告）日：2008-12-18

  Compounds of the formula I, in which R, X, R 1 , R 2 , R 3 , R 4 and R 5 have the meanings indicated in Claim 1 , are inhibitors of CHK1 CHK2 and SGK kinases and can be employed, inter alia, for the treatment of cancer.

  公式I的化合物，其中R、X、R1、R2、R3、R4和R5的含义如权利要求书中所示，是CHK1、CHK2和SGK激酶的抑制剂，可用于治疗癌症。
• A facile synthetic route for antineoplastic drug GDC-0449
  作者：Meng Cao、Hua-You Hu、Hu-Cheng Zhao、Xi-Quan Zhang、Hong-Mei Gu、Ling Yang、Jin Cai、Peng Wang、Bing Hu、Min Ji

  DOI：10.2478/s11696-014-0581-3

  日期：2014.1.1

  In the current study a facile synthetic route for preparing antineoplastic drug GDC-0449 is investigated. Starting with pyridine-1-oxide and 1-iodo-3-nitrobenzene, the intermediate product 2-(2-chloro-5-nitrophenyl) pyridine was prepared by cross-coupling, deoxidation and halogenation. The final compound was then synthesised by reduction of the nitro group followed by amidation. This synthetic route avoids the use of unstable organometallic or organic boride compounds; it employs relatively inexpensive and bench-stable reagents, involves readily controllable reaction conditions, and achieves a relatively high yield.

  在当前研究中，探讨了一种用于制备抗肿瘤药物GDC-0449的简便合成路线。从吡啶-1-氧化物和1-碘-3-硝基苯开始，通过交叉偶联、脱氧和卤代反应制备了中间产物2-(2-氯-5-硝基苯基)吡啶。然后通过还原硝基团和酰胺化合成了最终化合物。这种合成路线避免了使用不稳定的有机金属化合物或有机硼化合物；它采用相对廉价和台面稳定的试剂，涉及易于控制的反应条件，并实现了相对较高的产率。
• 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.
• Palladium-Catalyzed Aryl C(sp²)–H Bond Hydroxylation of 2-Arylpyridine Using TBHP as Oxidant
  作者：Jiawei Dong、Ping Liu、Peipei Sun

  DOI：10.1021/acs.joc.5b00167

  日期：2015.3.6

  An efficient synthesis of phenols via Pd-catalyzed, pyridyl-directed homogeneous hydroxylation of the aryl C-H bond was developed, in which tert-butyl hydroperoxide was used as the sole oxidant. The method had a broad group tolerance and was available for both electron-rich and electron-deficient substrates. The reaction of a series of 2-arylpyridine derivatives gave the ortho-hydroxylation products in moderate to good yields.
• Base-catalyzed rearrangement of N-(aryloxy)pyridinium salts. Effect of a 3-substituent in the pyridine ring upon orientation. Synthesis of novel tricyclic rings
  作者：Rudolph A. Abramovitch、Muthiah N. Inbasekaran、Shozo Kato、Teresa A. Radzikowska、Piotr Tomasik

  DOI：10.1021/jo00153a014

  日期：1983.3