5-(furan-2-yl)-3-phenyl-1H-pyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(furan-2-yl)-3-phenyl-1H-pyrazole
• 英文别名: 5-(2-furyl)-3-phenylpyrazole；3-furan-2-yl-5-phenyl-1(2)H-pyrazole；3-Phenyl-5--pyrazol；3(5)-Phenyl-5(3)furyl-2-pyrazol；3-Phenyl-5-(fur-2-yl)-pyrazolin
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: ZXRRQXOVEKCBQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(呋喃-2-基)-3-苯基丙烷-1,3-二酮 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 5-(furan-2-yl)-3-phenyl-1H-pyrazole
  参考文献：
  名称：

  Decoupling Activation of Heme Biosynthesis from Anaerobic Toxicity in a Molecule Active in Staphylococcus aureus

  摘要：

  Small molecules active in the pathogenic bacterium Staphylococcus aureus are valuable tools for the study of its basic biology and pathogenesis, and many molecules may provide leads for novel therapeutics. We have previously reported a small molecule, 1, which activates endogenous heme biosynthesis in S. aureus, leading to an accumulation of intracellular heme. In addition to this novel activity, 1 also exhibits toxicity towards S. aureus growing under fermentative conditions. To determine if these activities are linked and establish what features of the molecule are required for activity, we synthesized a library of analogs around the structure of 1 and screened them for activation of heme biosynthesis and anaerobic toxicity to investigate structure activity relationships. The results of this analysis suggest that these activities are not linked. Furthermore, we have identified the structural features that promote each activity and have established two classes of molecules: activators of heme biosynthesis and inhibitors of anaerobic growth. These molecules will serve as useful probes for their respective activities without concern for the off target effects of the parent compound.

  DOI：

  10.1021/acschembio.5b00934

文献信息

• One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling–intramolecular cyclization
  作者：Narasimha Swamy Thirukovela、Ramesh Balaboina、Vinayak Botla、Ravinder Vadde、Sreekantha Babu Jonnalagadda、Chandra Sekhar Vasam

  DOI：10.1039/c9cy01335k

  日期：——

  Catalyst efficacy of in situ generated Pd-nanoparticles (PdNPs) in the regioselective one-pot synthesis of 3,5-di & 3,4,5-trisubstituted pyrazoles and 3,5-disubstituted isoxazoles in environmentally benign PEG-400/H2O medium, which involves the sequential (i) Cu-free acyl-Sonogashira coupling (ASC) and (ii) intramolecular ynone–amine cyclization under PTC conditions was described. The results of controlled

  在环境友好的PEG-400 / H 2中原位生成的Pd-纳米颗粒（PdNPs）在区域选择性一锅合成3,5-di和3,4,5-三取代的吡唑和3,5-二取代的异恶唑的催化剂效力描述了一种O介质，它涉及（i）在PTC条件下无Cu的酰基-Sonogashira偶联（ASC）和（ii）分子内的ynone-amine环化。受控实验的结果支持两个连续的催化循环（ASC /环化）的操作，并通过一锅法通过与炔酮结合的钯实现互补/相反的区域选择性。而且，就地一锅法反应序列的第一个催化循环后回收的PdNPs已连续五次再次使用。此外，在进行上述研究之前，某些常见的Pd-N-杂环卡宾（Pd-NHC）配合物在水和有机物中催化相同的一锅两步反应顺序（无铜ASC /环化）的功效还优化了溶剂。还可以从水中的Pd-NHC上方原位生成PdNP，但由于它们的尺寸较大，因此无法重复使用。
• A highly efficient heterogeneous palladium-catalyzed cascade three-component reaction of acid chlorides, terminal alkynes and hydrazines leading to pyrazoles
  作者：Qiurong Chen、Fang Yao、Lin Yin、Mingzhong Cai

  DOI：10.1016/j.jorganchem.2015.12.037

  日期：2016.2

  MCM-41-immobilized palladium(II) complex [MCM-41-2N–Pd(OAc)2] and 1.0 mol% of CuI, acid chlorides were coupled with terminal alkynes in Et3N at 50 °C to give α,β-unsaturated ynones, which were converted in situ into pyrazoles by the cycloaddition of hydrazines at room temperature with acetonitrile as cosolvent. The cascade reactions generated a variety of pyrazole derivatives in moderate to good yields, and

  在0.5摩尔％的3-（2-氨基乙基氨基）丙基官能化的MCM-41固定的钯（II）配合物[MCM-41-2N-Pd（OAc）2 ]和1.0摩尔％的CuI的存在下，酰氯将其与末端炔烃在50°C的Et 3 N中偶合，得到α，β-不饱和炔酮，通过在室温下以乙腈为助溶剂将肼环加成，将其原位转化为吡唑。级联反应以中等至良好的产率生成了多种吡唑衍生物，并且这种非均相钯催化剂显示出比PdCl 2（PPh 3）2更高的催化活性，并且可以被回收并重复使用至少10次连续试验而活性没有降低。
• Compostions and Methods for Controlling Nematodes
  申请人：Williams Deryck J.

  公开号：US20090048311A1

  公开（公告）日：2009-02-19

  Compositions and processes for controlling nematodes are described herein, e.g., nematodes that infest plants or animals. The compounds include oxazoles, oxadiazoles and thiadiazoles.

  本文描述了用于控制线虫的组合物和过程，例如侵害植物或动物的线虫。这些化合物包括噁唑、噁二唑和噻二唑。
• [EN] COMPOSITIONS AND METHODS FOR IMPROVING AGRONOMIC CHARACTERISTICS OF PLANTS<br/>[FR] COMPOSITIONS ET PROCÉDÉS DESTINÉS À AMÉLIORER DES CARACTÉRISTIQUES AGRONOMIQUES DE PLANTES
  申请人：MONSANTO TECHNOLOGY LLC

  公开号：WO2016100766A1

  公开（公告）日：2016-06-23

  Compounds, compositions and methods for improving one or more agronomic characteristics of desired crop plants are described herein. The compounds include oxazoles, oxadiazoles and thiadiazoles.

  本文描述了改善所需作物植物一种或多种农艺特性的化合物、组合物和方法。这些化合物包括噁唑、噁二唑和噻二唑。
• Fast and Efficient Continuous Flow Method for the Synthesis of Ynones and Pyrazoles
  作者：Mohanraj Kandasamy、Balaji Ganesan、Min-Yuan Hung、Wei-Yu Lin

  DOI：10.1002/ejoc.201900468

  日期：2019.6.2

  An efficient method for the synthesis of ynones and polysubstituted pyrazoles in a continuous flow system through the generation of activated lithium acetylide. This system serves as a powerful strategy for a rapid, easy, and transition metal free process performed under mild reaction conditions, which provides a better reagent controll compared to the available benchtop methods.

  通过生成活化的乙炔锂，在连续流动系统中合成炔酮和多取代的吡唑的有效方法。该系统是在温和的反应条件下进行快速，简便和无过渡金属过程的有力策略，与台式方法相比，该方法可提供更好的试剂控制。