methyl 2,2-difluoro-5-phenylpentanoate | 1093167-46-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2,2-difluoro-5-phenylpentanoate
• 英文别名: Benzenepentanoic acid, alpha,alpha-difluoro-, methyl ester
• CAS: 1093167-46-4
• 化学式: C₁₂H₁₄F₂O₂
• 分子量: 228.239
• InChiKey: RBCCFZJHQBZIDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,2-difluoro-5-phenylpentanoate 在 (三氟甲基)三甲基硅烷 、 cesium fluoride 作用下， 以 乙二醇二甲醚 为溶剂， 生成 1,1,1,3,3-pentafluoro-6-phenylhexane-2,2-diol
  参考文献：
  名称：

  Synthesis of Polyfluoro Ketones for Selective Inhibition of Human Phospholipase A₂ Enzymes

  摘要：

  The development of selective inhibitors for individual PLA(2) enzymes is necessary in order to target PLA(2)-specific signaling pathways, but it is challenging due to the observed promiscuity of known PLA(2) inhibitors. In the current work, we present the development and application of a variety of synthetic routes to produce pentafluoro, tetrafluoro, and trifluoro derivatives of activated carbonyl groups in order to screen for selective inhibitors and characterize the chemical properties that can lead to selective inhibition. Our results demonstrate that the pentafluoroethyl ketone functionality favors selective inhibition of the GVIA iPLA(2), a very important enzyme for which specific, potent, reversible inhibitors are needed. We find that 1,1,1,2,2-pentafluoro-7-phenyl-heptan-3-one (FKGK11) is a selective inhibitor of GVIA iPLA(2) (X-1(50) = 0.0073). Furthermore, we conclude that the introduction of an additional fluorine atom at the alpha' position of a trifluoromethyl ketone constitutes an important strategy for the development of new potent GVIA iPLA(2) inhibitors.

  DOI：

  10.1021/jm800649q
• 作为产物：
  描述：

  methyl 2-oxo-5-phenylpentanoate 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到methyl 2,2-difluoro-5-phenylpentanoate
  参考文献：
  名称：

  Synthesis of Polyfluoro Ketones for Selective Inhibition of Human Phospholipase A₂ Enzymes

  摘要：

  The development of selective inhibitors for individual PLA(2) enzymes is necessary in order to target PLA(2)-specific signaling pathways, but it is challenging due to the observed promiscuity of known PLA(2) inhibitors. In the current work, we present the development and application of a variety of synthetic routes to produce pentafluoro, tetrafluoro, and trifluoro derivatives of activated carbonyl groups in order to screen for selective inhibitors and characterize the chemical properties that can lead to selective inhibition. Our results demonstrate that the pentafluoroethyl ketone functionality favors selective inhibition of the GVIA iPLA(2), a very important enzyme for which specific, potent, reversible inhibitors are needed. We find that 1,1,1,2,2-pentafluoro-7-phenyl-heptan-3-one (FKGK11) is a selective inhibitor of GVIA iPLA(2) (X-1(50) = 0.0073). Furthermore, we conclude that the introduction of an additional fluorine atom at the alpha' position of a trifluoromethyl ketone constitutes an important strategy for the development of new potent GVIA iPLA(2) inhibitors.

  DOI：

  10.1021/jm800649q

文献信息

• Photoredox Catalysis Mediated Application of Methyl Fluorosulfonyldifluoroacetate as the CF₂CO₂R Radical Source
  作者：Wei Yu、Xiu-Hua Xu、Feng-Ling Qing

  DOI：10.1021/acs.orglett.6b02580

  日期：2016.10.7

  A new application of trifluoromethylating reagent, methyl fluorosulfonyldifluoroacetate (FO2SCF2CO2Me, Chen’s reagent), as the carbomethoxydifluoromethylating reagent under visible light photoredox conditions is reported. The visible-light-induced reaction of FO2SCF2CO2Me with unactivated alkenes, styrenes, or heteroarenes affords a variety of carbomethoxydifluoromethylated products.

  报道了三氟甲基化试剂，氟磺酰基二氟乙酸甲酯（FO 2 SCF 2 CO 2 Me，Chen氏试剂）在可见光光氧化还原条件下作为羧甲氧基二氟甲基化试剂的新应用。FO 2 SCF 2 CO 2 Me与未活化的烯烃，苯乙烯或杂芳烃的可见光诱导反应产生了多种甲氧基二氟甲基化产物。
• Synthesis of Polyfluoro Ketones for Selective Inhibition of Human Phospholipase A₂ Enzymes
  作者：Constantinos Baskakis、Victoria Magrioti、Naomi Cotton、Daren Stephens、Violetta Constantinou-Kokotou、Edward A. Dennis、George Kokotos

  DOI：10.1021/jm800649q

  日期：2008.12.25

  The development of selective inhibitors for individual PLA(2) enzymes is necessary in order to target PLA(2)-specific signaling pathways, but it is challenging due to the observed promiscuity of known PLA(2) inhibitors. In the current work, we present the development and application of a variety of synthetic routes to produce pentafluoro, tetrafluoro, and trifluoro derivatives of activated carbonyl groups in order to screen for selective inhibitors and characterize the chemical properties that can lead to selective inhibition. Our results demonstrate that the pentafluoroethyl ketone functionality favors selective inhibition of the GVIA iPLA(2), a very important enzyme for which specific, potent, reversible inhibitors are needed. We find that 1,1,1,2,2-pentafluoro-7-phenyl-heptan-3-one (FKGK11) is a selective inhibitor of GVIA iPLA(2) (X-1(50) = 0.0073). Furthermore, we conclude that the introduction of an additional fluorine atom at the alpha' position of a trifluoromethyl ketone constitutes an important strategy for the development of new potent GVIA iPLA(2) inhibitors.