2-氟-3-氧代-3-苯基丙腈 | 343271-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-氟-3-氧代-3-苯基丙腈
• 英文名称: 2-fluoro-3-oxo-3-phenylpropanenitrile
• CAS: 343271-85-2
• 化学式: C₉H₆FNO
• 分子量: 163.151
• InChiKey: KDBUXQMYUUDVDV-UHFFFAOYSA-N

物化性质

• 沸点：
  276.6±25.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-氟-3-氧代-3-苯基丙腈 在 一水合肼 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 、 三氯氧磷 作用下， 以 二苯醚 、 联苯 、 乙醚 、 乙醇 、 水 为溶剂， 反应 38.0h， 生成 3-fluoro-2-phenyl-N-(pyridin-3-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine
  参考文献：
  名称：

  Simple approach to the synthesis of 3-fluoro pyrazolo[1,5-a]pyrimidine analogues

  摘要：

  A simple method for the synthesis of novel 3-fluoro pyrazolo[1,5-a]pyrimidine analogues has been developed starting from fluoro acetonitrile and benzoyl chloride. The desired compounds are synthesized from a 3-amino-4-fluoro pyrazole intermediate. The versatility of the approach was demonstrated by the synthesis of a small library of pyrazolo[1,5-a]pyrimidine. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.015
• 作为产物：
  描述：

  苯甲酰乙腈 在 1-乙烯基-3-丁基咪唑氯盐 、 Selectfluor 作用下， 反应 15.0h， 以29%的产率得到2-氟-3-氧代-3-苯基丙腈
  参考文献：
  名称：

  Mild and selective α-fluorination of carbonyl compounds (ketones, 1,3-diketones, β-ketoesters, α-nitroketones, and β-ketonitriles) with Selectfluor (F-TEDA-BF4) in imidazolium ILs [BMIM/PF6 or BMIM/NTf2] with Brønsted-acidic IL [PMIM(SO3H)/OTf] as promoter

  摘要：

  Structurally diverse ketones, 1,3-diketones, and beta-ketoesters, were selectively monofluorinated with Selectfluor (F-TEDA-BF4) (1 equiv) in [BMIM][PF6] as solvent and [PMIM(SO3H)][OTf] as promoter under mild conditions. In selected cases, the monofluorinated products were transformed to the gem-difluoro derivatives by employing an additional equivalent of Selectfluor, and gem-difluoro-derivatives were synthesized directly from the substrates by employing 2 equiv of Selectfluor. The method was extended to monofluorination of representative alpha-nitroketones and beta-ketonitriles using [BMIM][NTf2] without the need for promoters. The described method offers the added advantage of recycling and reuse of the IL solvent.

  DOI：

  10.1016/j.tetlet.2015.07.084

文献信息

• [EN] THIENO [2, 3-B] PYRIDINE DERIVATIVES AS VIRAL REPLICATION INHIBITORS<br/>[FR] DÉRIVÉS DE LA THIÉNO [2, 3-B] PYRIDINE EN TANT QU'INHIBITEURS DE RÉPLICATION VIRALE
  申请人：UNIV LEUVEN KATH

  公开号：WO2010130842A1

  公开（公告）日：2010-11-18

  The present invention relates to a series of compounds of formula (A) having antiviral activity, more specifically HIV (Human Immunodeficiency Virus) replication inhibiting properties. The invention also relates to methods for the preparation of such compounds, as well as to novel intermediates useful in one or more steps of such syntheses. The invention also relates to pharmaceutical compositions comprising an effective amount of such compounds as active ingredients. This invention further relates to the use of such compounds as medicines or in the manufacture of a medicament useful for the treatment of animals suffering from viral infections, in particular HIV infection. This invention further relates to methods for the treatment of viral infections in animals by the administration of a therapeutical amount of such compounds, optionally combined with one or more other drugs having anti-viral activity.

  本发明涉及一系列具有抗病毒活性的化合物(A)的公式，更具体地说是具有抑制HIV（人类免疫缺陷病毒）复制的特性。该发明还涉及制备这类化合物的方法，以及在这类合成的一个或多个步骤中有用的新中间体。该发明还涉及包含有效量这类化合物作为活性成分的药物组合物。本发明进一步涉及将这类化合物用作药物或用于制造用于治疗患有病毒感染的动物，尤其是HIV感染的药物。本发明还涉及通过给予这类化合物的治疗量，可选地与一个或多个具有抗病毒活性的其他药物结合，来治疗动物的病毒感染的方法。
• New Synthesis of Fluorinated Pyrazoles
  作者：Riccardo Surmont、Guido Verniest、Norbert De Kimpe

  DOI：10.1021/ol1019713

  日期：2010.10.15

  A new synthesis of fluorinated pyrazoles, a class of compounds with potential in medicinal chemistry, is described. The treatment of benzoylfluoroacetonitrile with hydrazine yielded the expected new 3-amino-4-fluoropyrazole, while the analogous reaction of α-cyano-α,α-difluoroketones with hydrazine in refluxing isopropanol surprisingly gave rise to 3-unsubstituted 4-fluoropyrazoles via an unprecedented

  描述了一种氟化吡唑的新合成方法，它是一类在药物化学中具有潜力的化合物。用肼处理苯甲酰氟乙腈可得到预期的新的3-氨基-4-氟吡唑，而α-氰基-α，α-二氟酮与肼在异丙醇回流中的类似反应令人惊讶地通过空前的反应生成了3-未取代的4-氟吡唑机制。中间体肼加合物的分离导致该转化的机理基础。
• A Pd-Catalyzed [4 + 2] Annulation Approach to Fluorinated N-Heterocycles
  作者：Víctor García-Vázquez、Larry Hoteite、Christopher P. Lakeland、David W. Watson、Joseph P. A. Harrity

  DOI：10.1021/acs.orglett.1c00752

  日期：2021.4.2

  3-Fluoro- and trifluoromethylthio-piperidines represent important building blocks for discovery chemistry. We report a simple and efficient method to access analogs of these compounds that are armed with rich functionality allowing them to be chemoselectively derivatized with high diastereocontrol.

  3-氟和三氟甲硫基哌啶是发现化学的重要组成部分。我们报告了一种简单有效的方法，可访问具有丰富功能的这些化合物的类似物，从而可以通过非对映异构体的高度化学控制对其进行化学选择性衍生化。
• Potential antiarthritic agents. 2. Benzoylacetonitriles and .beta.-aminocinnamonitriles
  作者：David N. Ridge、J. William Hanifin、Linda A. Harten、Bernard D. Johnson、Judith Menschik、Gabriela Nicolau、Adolph E. Sloboda、Doris E. Watts

  DOI：10.1021/jm00197a020

  日期：1979.11

  Benzoylacetonitrile and beta-aminocinnamonitrile are shown to possess potent antiinflammatory activity in the rat adjuvant arthritis model. In a series of phenyl-substituted analogues, only o-, m-, and p-fluorobenzoylacetonitrile and m- and p-fluoro-beta-aminocinnamonitrile retained activity. Additionally, beta-amino-2- and beta-amino-3-thiopheneacrylonitrile and beta-oxo-2- and beta-oxo-3-thiophenepropionitrile

  在大鼠佐剂性关节炎模型中，苯甲酰乙腈和β-氨基肉桂腈显示出有效的抗炎活性。在一系列苯基取代的类似物中，仅邻，间和对氟苯甲酰基乙腈以及间和对氟β-氨基肉桂腈保留了活性。另外，β-氨基-2-和β-氨基-3-噻吩丙烯腈以及β-氧代-2-和β-氧代-3-噻吩丙腈表现出相似的活性。不认为这些试剂通过前列腺素合成酶抑制起作用。还描述了苯甲酰基乙腈的代谢特征。
• Synthesis of Novel 4-Fluoro-2H-pyrazol-3-ylamines
  作者：Giuseppe Cocconcelli、Chiara Ghiron、Simon Haydar、Iolanda Micco、Riccardo Zanaletti

  DOI：10.1080/00397910903277912

  日期：2010.8.5

  A new and efficient synthesis for the preparation of novel 4-fluoro-2H-pyrazol-3-ylamines is described. It involves the reaction of an acyl chloride with fluoroacetonitrile and sequential ring closure of the α-fluoro-β-ketonitrile with hydrazine. Utilizing this synthetic protocol, we have synthesized a variety of 4-fluoro-2H-pyrazol-3-ylamines with different steric and electronic demands.

  描述了一种用于制备新型 4-氟-2H-吡唑-3-基胺的新型有效合成方法。它涉及酰氯与氟乙腈的反应以及 α-氟-β-酮腈与肼的连续闭环反应。利用该合成方案，我们合成了各种具有不同空间和电子需求的 4-fluoro-2H-pyrazol-3-ylamines。