2-氟-1-(3-氟-4-甲氧基苯基)乙酮 | 501426-62-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-氟-1-(3-氟-4-甲氧基苯基)乙酮
• 英文名称: 2,3'-difluoro-4'-methoxyacetophenone
• 英文别名: 2-fluoro-1-(3-fluoro-4-methoxyphenyl)ethanone；2-Fluoro-1-(3-fluoro-4-methoxyphenyl)ethan-1-one
• CAS: 501426-62-6
• 化学式: C₉H₈F₂O₂
• 分子量: 186.158
• InChiKey: QDYRWKURPIEHFM-UHFFFAOYSA-N

物化性质

• 熔点：
  82–84°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氟-4-甲氧基苯乙酮 在 甲醇 、 Selectfluor 、 水 作用下， 反应 1.25h， 以59%的产率得到2-氟-1-(3-氟-4-甲氧基苯基)乙酮
  参考文献：
  名称：

  微波辅助氟化：取代的1-芳基酮的侧链氟化的改进方法

  摘要：

  已经开发了一种两步一锅微波（MW）辅助将1-蒽酮氟化为相应的1-芳基-2-氟乙酮的方法。第一步利用Selectfluor™作为甲醇中的氟化剂，形成1-芳基-2-氟乙酮及其相应的二甲基乙缩醛。在第二步中，添加水，并且Selectfluor™在二甲基乙缩醛的水解裂解中充当路易斯酸。与热合成相比，MW辅助方法可减少氟化反应和二甲基乙缩醛反应的反应时间。而且，一锅法减少了试剂和溶剂的消耗。该方法最适合于制备含有可钝化亲电芳族取代基的取代基的1-芳基-2-氟乙酮，但高度缺电子的酮如1-（3，5-二硝基苯基）乙酮反应更慢。使用富含电子的芳族酮进行的反应具有较低的区域选择性，并且还产生了氟代芳族产物。

  DOI：

  10.1016/j.tet.2009.09.070

文献信息

• PYRAZOLONE DERIVATIVE AND PDE INHIBITOR CONTAINING THE SAME AS ACTIVE INGREDIENT
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：EP2168960A1

  公开（公告）日：2010-03-31

  It is to provide a novel pyrazolone derivative represented by the following general formula (1), which is useful as a pharmaceutical and has a phosphodiesterase inhibitory action: wherein R1,R2: C1-6 alkyl; R3,R4: H, X, C1-6 alkoxy; Z:O, S; A:AA, BB, wherein AA represents wherein BB represents wherein R5: H, C1-6 alkyl ; R6,R7: C1-6 alkyl.

  提供一种新颖的吡唑酮衍生物， represented by the following general formula (1)，该衍生物可用作药物，并具有磷酸二酯酶抑制作用： 其中 R1，R2：C1-6烷基；R3，R4：H，X，C1-6烷氧基；Z：O，S；A：AA，BB，其中AA代表 其中BB代表 其中R5：H，C1-6烷基；R6，R7：C1-6烷基。
• PYRIDAZINONE DERIVATIVE AND PDE INHIBITOR CONTAINING THE SAME AS ACTIVE INGREDIENT
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：EP2168959A1

  公开（公告）日：2010-03-31

  It is to provide a novel pyridazinone derivative represented by the following general formula (1), which is useful as a pharmaceutical and has a phosphodiesterase inhibitory action: wherein R1 represents H or C1-6 alkyl, each of R2 and R3 represents H, X, C1-6 alkoxy, Z represents O or S, and A represents AA or BB, wherein AA represents: and BB represents: wherein R4 represents H or C1-6 alkyl, and each of R5 and R6 represents C1-6 alkyl.

  提供一种新颖的吡啶并酮衍生物，其通式如下（1），可用作药物，并具有磷酸二酯酶抑制作用： 其中R1代表H或C1-6烷基，R2和R3各自代表H、X、C1-6烷氧基，Z代表O或S，A代表AA或BB，其中AA代表： 而BB代表： 其中R4代表H或C1-6烷基，R5和R6各自代表C1-6烷基。
• Electrophilic and nucleophilic side chain fluorination of para-substituted acetophenones
  作者：Erik Fuglseth、Thor Håkon Krane Thvedt、Maria Førde Møll、Bård Helge Hoff

  DOI：10.1016/j.tet.2008.05.060

  日期：2008.7

  para-Substituted alpha-fluoroacetophenones have been synthesised by three different routes. Electrophilic fluorination of trimethylsilyl enol ethers of acetophenones using Selectfluor (F-TEDA-BF4, 1-chloromethyl-4-fluoro- 1,4-diazoniabicyclo[ 2.2.2]octane bis-(tetrafluoroborate)) gave high to moderate yield depending on the electronic properties of the substituents. F-TEDA-BF4 mediated fluorination of acetophenones in methanol resulted in a mixture of alpha-fluoroacetophenones and the corresponding 2-fluoro- 1,1 -dimethyl acetals. The dimethyl acetals were hydrolysed using trifluoroacetic acid in water to maximise the yield of the product. Nucleophilic fluorination of alpha-bromoacetophenones using tetrabutylammoniurn hydrogen bifluoride (TBABF) led to moderate yield when having electron-donating substituents, whereas low yields were experienced when more electron-withdrawing substituents were introduced. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis, Structure−Activity Relationship, and Evaluation of SR141716 Analogues:  Development of Central Cannabinoid Receptor Ligands with Lower Lipophilicity
  作者：Reeti Katoch-Rouse、Olga A. Pavlova、Tara Caulder、Alexander F. Hoffman、Alexey G. Mukhin、Andrew G. Horti

  DOI：10.1021/jm020157x

  日期：2003.2.1

  Exploration of the central CB1 cannabinoid receptors using positron emission tomography (PET) will allow for an understanding of the pharmacological and physiological role played by these receptors in the CNS. Current tracers are highly lipophilic compounds that exhibit very high nonspecific to specific binding ratios and as a result are inapt for use in humans. We have synthesized a series of less lipophilic analogues of SR141716 to serve as potential radioligands. Binding affinities of the series and a functional electrophysiological assay of three of our compounds have been presented.
• Microwave assisted fluorination: an improved method for side chain fluorination of substituted 1-arylethanones
  作者：Thor Håkon Krane Thvedt、Erik Fuglseth、Eirik Sundby、Bård Helge Hoff

  DOI：10.1016/j.tet.2009.09.070

  日期：2009.11

  microwave (MW) assisted fluorination of 1-arylethanones to their corresponding 1-aryl-2-fluoroethanones has been developed. The first step utilises Selectfluor™ as a fluorinating agent in methanol forming 1-aryl-2-fluoroethanones and their corresponding dimethyl acetals. In the second step, water is added and Selectfluor™ acts as a Lewis acid in the hydrolytic cleavage of the dimethyl acetals. Compared to

  已经开发了一种两步一锅微波（MW）辅助将1-蒽酮氟化为相应的1-芳基-2-氟乙酮的方法。第一步利用Selectfluor™作为甲醇中的氟化剂，形成1-芳基-2-氟乙酮及其相应的二甲基乙缩醛。在第二步中，添加水，并且Selectfluor™在二甲基乙缩醛的水解裂解中充当路易斯酸。与热合成相比，MW辅助方法可减少氟化反应和二甲基乙缩醛反应的反应时间。而且，一锅法减少了试剂和溶剂的消耗。该方法最适合于制备含有可钝化亲电芳族取代基的取代基的1-芳基-2-氟乙酮，但高度缺电子的酮如1-（3，5-二硝基苯基）乙酮反应更慢。使用富含电子的芳族酮进行的反应具有较低的区域选择性，并且还产生了氟代芳族产物。