1-(4-氟苯基)-2-(吡啶-2-基)乙酮 | 366-62-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-氟苯基)-2-(吡啶-2-基)乙酮
• 英文名称: 1-(4-fluorophenyl)-2-(pyridin-2-yl)ethanone
• 英文别名: 2-(4-Fluor-phenacyl)-pyridin；1-(4-Fluorophenyl)-2-pyridin-2-ylethanone
• CAS: 366-62-1
• 化学式: C₁₃H₁₀FNO
• 分子量: 215.227
• InChiKey: HSXYDJFTGOBXIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-氟苯基)-2-(吡啶-2-基)乙酮 在 盐酸 、 ammonium acetate 、 sodium nitrite 、 亚磷酸三乙酯 作用下， 以 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 4-[4-(4-fluorophenyl)-5-(2-pyridyl)-1H-imidazol-2-yl]benzonitrile
  参考文献：
  名称：

  Identification of Novel Inhibitors of the Transforming Growth Factor β1 (TGF-β1) Type 1 Receptor (ALK5)

  摘要：

  Screening of our internal compound collection for inhibitors of the transforming growth factor beta1 (TGF-beta1) type I receptor (ALK5) identified several hits. Optimization of the dihydropyrroloimidazole hit 2 by introduction of a 2-pyridine and 3,4-methylenedioxyphenyl group gave 7, a selective ALK5 inhibitor. With this information, optimization of the triarylimidazole hit 8 gave the selective inhibitor 14, which inhibits TGF-beta1-induced fibronectin mRNA formation while displaying no measurable cytotoxicity in the 48 h XTT assay.

  DOI：

  10.1021/jm010493y
• 作为产物：
  描述：

  (Z)-1-(4-Fluoro-phenyl)-2-pyridin-2-yl-ethenol 以 氘代氯仿 为溶剂， 生成 1-(4-氟苯基)-2-(吡啶-2-基)乙酮
  参考文献：
  名称：

  Kolehmainen, Erkki; Osmiaowski, Borys; Nissinen, Maija, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 11, p. 2185 - 2191

  摘要：

  DOI：

文献信息

• Sequence‐Dependent Stereodivergent Allylic Alkylation/Fluorination of Acyclic Ketones
  作者：Xi‐Jia Liu、Shicheng Jin、Wen‐Yun Zhang、Qiang‐Qiang Liu、Chao Zheng、Shu‐Li You

  DOI：10.1002/anie.201912882

  日期：2020.1.27

  The stereodivergent iridium-catalyzed allylic alkylation and fluorination of acyclic ketones is described. α-Pyridyl-α-fluoroketones with vicinal tertiary and quaternary stereocenters were obtained in moderate to excellent yields and stereoselectivities. Distinct from known stereodivergent synthesis, for which two different chiral catalysts are required in general, herein we report a sequence-dependent

  描述了立体发散的铱催化的烯丙基烷基化和无环酮的氟化。获得具有邻近的叔和四级立体中心的α-吡啶基-α-氟代酮，具有中等至极好的收率和立体选择性。与通常需要两种不同的手性催化剂的已知立体发散性合成不同，本文中我们报道了序列依赖性立体发散性合成。仅使用一种手性Ir催化剂，通过简单地调节不对称烯丙基烷基化和氟化的顺序并改变Ir催化剂的绝对构型，就可以从相同的起始原料制备产物的所有四种可能的立体异构体。
• Highly efficient asymmetric bioreduction of 1-aryl-2-(azaaryl)ethanones. Chemoenzymatic synthesis of lanicemine
  作者：Ramón Liz、Elisa Liardo、Francisca Rebolledo

  DOI：10.1039/c9ob01616c

  日期：——

  1-Aryl-2-(azaaryl)ethanols with ee > 99% have been prepared by KRED-catalyzed reduction of the ketone precursors. A chemoenzymatic synthesis of lanicemine is described.

  1-芳基-2-(氮杂芳基)乙醇，ee > 99%，通过KRED催化的酮前体还原制备。描述了一种兰尼西明的化学酶合成方法。
• Synthesis of functionalised 4H-quinolizin-4-ones via tandem Horner–Wadsworth–Emmons olefination/cyclisation
  作者：Calum W. Muir、Alan R. Kennedy、Joanna M. Redmond、Allan J. B. Watson

  DOI：10.1039/c3ob40578h

  日期：——

  4H-Quinolizin-4-ones are a unique class of heterocycle with valuable physicochemical properties and which are emerging as key pharmacophores for a range of biological targets. A tandem Horner–Wadsworth–Emmons olefination/cyclisation method has been developed to allow facile access to substituted 4H-quinolizin-4-ones encoded with a range of functional groups.

  4H-喹啉-4-酮是一类独特的杂环化合物，具有宝贵的物理化学性质，并且正在成为多种生物靶点的重要药效团。已经开发了一种串联的霍纳-瓦兹沃斯-埃蒙斯烯化/环化方法，以便容易获得具有多种功能基团的取代4H-喹啉-4-酮。
• Pyrazolopyridines
  申请人：SmithKline Beecham Corporation

  公开号：US06498166B1

  公开（公告）日：2002-12-24

  The invention provides the compounds of formula (I) wherein: R0 and R1 are independently selected from H, halogen, C1-6alkyl, C1-6alkoxy, or C1-6alkoxy substituted by one or more fluorine atoms; R2 is halogen, CN, CONR4R5, CO2H, CO2C1-6alkyl, or NHSO2R4; R3 is C1-6alkyl or NH2; and R4 and R5 are independently selected from H, C1-6alkyl, phenyl, phenyl substituted by one or more atoms or groups (selected from halogen, C1-6alkyl, C1-6alkoxy, or C1-6alkoxy substituted by one or more fluorine atoms), or together with the nitrogen atom to which they are attached form a saturated 4 to 8 membered ring; and pharmaceutically acceptable derivatives thereof. Compounds of formula (I) are potent and selective inhibitors of COX-2 and are of use in the treatment of the pain, fever, inflammation of a variety of conditions and diseases.

  该发明提供了以下式（I）的化合物：其中：R0和R1分别选择自H、卤素、C1-6烷基、C1-6烷氧基或由一个或多个氟原子取代的C1-6烷氧基；R2是卤素、CN、CONR4R5、CO2H、CO2C1-6烷基或NHSO2R4；R3是C1-6烷基或NH2；以及R4和R5分别选择自H、C1-6烷基、苯基、苯基取代一个或多个原子或基团（选择自卤素、C1-6烷基、C1-6烷氧基或由一个或多个氟原子取代的C1-6烷氧基），或与它们连接的氮原子一起形成饱和的4到8成员环；以及其药用可接受的衍生物。式（I）的化合物是强效和选择性的COX-2抑制剂，可用于治疗各种疾病和疾病的疼痛、发热、炎症。
• Mild Metal-Free Sequential Dual Oxidative Amination of C(sp³)–H bonds: Efficient Synthesis of Imidazo[1,5-<i>a</i>]pyridines
  作者：Yizhe Yan、Yonghui Zhang、Zhenggen Zha、Zhiyong Wang

  DOI：10.1021/ol4008487

  日期：2013.5.3

  A metal-free sequential dual oxidative amination of C(sp3)–H bonds under ambient conditions was the first developed, affording imidazo[1,5-a]pyridines in good to excellent yields. The reaction was involved in two oxidative C–N couplings and one oxidative dehydrogenation process with six hydrogen atoms removed.

  首次开发了在环境条件下无金属的C（sp 3）-H键的顺序双氧化胺化反应，可提供咪唑并[1,5- a ]吡啶，并具有良好或优异的收率。该反应涉及两个氧化C–N偶联和一个氧化脱氢过程，其中去除了六个氢原子。