4-(4-benzyloxyphenyl)-1,1,1-trifluorobutan-2-one | 221912-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-benzyloxyphenyl)-1,1,1-trifluorobutan-2-one
• 英文别名: 4-(4-benzyloxyphenyl)-1,1,1-trifluoro-2-butanone；1,1,1-trifluoro-4-(4-benzyloxy-phenyl)-2-butanone；4-[4-(Benzyloxy)phenyl]-1,1,1-trifluorobutan-2-one；1,1,1-trifluoro-4-(4-phenylmethoxyphenyl)butan-2-one
• CAS: 221912-94-3
• 化学式: C₁₇H₁₅F₃O₂
• 分子量: 308.3
• InChiKey: CPWKNIBKQUNVFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-benzyloxyphenyl)-1,1,1-trifluorobutan-2-one 在 三甲基氯硅烷 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到4-(4-Benzyloxyphenyl)-1, 1,1-trifluoro-2-trimethylsilyloxy-2-butene
  参考文献：
  名称：

  Alpha-and beta-substituted trifluoromethyl ketones as phospholipase inhibitors

  摘要：

  提供了抑制细胞质磷脂酶A2酶的抑制剂，可用于控制各种炎症性疾病。本发明的抑制剂具有一般公式，其中X、Z、R1、R2、R3、R4、Ra和Rb如规范中所定义。

  公开号：

  US06414179B1
• 作为产物：
  描述：

  3-<4-(benzyloxy)phenyl>-propanoyl chloride 、 三氟乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 4-(4-benzyloxyphenyl)-1,1,1-trifluorobutan-2-one
  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

• Alpha-and beta- substituted trifluoromethyl ketones as phospholipase inhibitors
  申请人：——

  公开号：US20020065246A1

  公开（公告）日：2002-05-30

  Inhibitors of the cytosolic phospholipase A2 enzymes are provided which are of use in controlling a wide variety of inflammatory diseases. The inhibitors of the present invention have the general formula 1 where X, Z, R 1 , R 2 , R 3 , R 4 , R a and R b are as defined in the specification.

  提供了细胞质磷脂酶A2酶的抑制剂，可用于控制各种炎症性疾病。本发明的抑制剂具有一般公式1，其中X、Z、R1、R2、R3、R4、Ra和Rb如规范中所定义。
• PERFLUOROKETONE COMPOUNDS AND USES THEREOF
  申请人：David Samuel

  公开号：US20100048727A1

  公开（公告）日：2010-02-25

  Novel perfluoroketone compounds of formula [I] and [Ia] are described. Also described are uses thereof, such as for inhibition of phospholipase A 2 activity. Therapeutic uses thereof are also described, such as for the treatment of neural conditions and/or inflammatory conditions, such as demyelinating (e.g., multiple sclerosis) and neural injury (e.g., spinal cord injury).

  本文描述了化学式[I]和[Ia]的新型全氟酮化合物。还描述了它们的用途，例如用于抑制磷脂酶A2活性。还描述了它们的治疗用途，例如用于治疗神经疾病和/或炎症疾病，如脱髓鞘（例如多发性硬化症）和神经损伤（例如脊髓损伤）。
• US6414179B1
  申请人：——

  公开号：US6414179B1

  公开（公告）日：2002-07-02
• [EN] PERFLUOROKETONE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE PERFLUOROCÉTONE ET LEURS UTILISATIONS
  申请人：UNIV MCGILL

  公开号：WO2008122119A1

  公开（公告）日：2008-10-16

  [EN] Novel perfluoroketone compounds of formula [I] and [Ia] are described Also described are uses thereof, such as for inhibition of phospholipase A₂ activity. Therapeutic uses thereof are also described, such as for the treatment of neural conditions and / or inflammatory conditions, such as demeyelmatmg (e.g., multiple sclerosis) and neural injury (e.g., spinal cord injury).
  [FR] L'invention concerne de nouveaux composés de perfluorocétone. Elle concerne également leurs utilisations, par exemple, pour inhiber l'activité de phospholipase A2. Elle concerne également leurs utilisations thérapeutiques, par exemple, pour traiter des états neuraux et/ou inflammatoires, tels que la démyélinisation (par exemple, la sclérose en plaques) et la lésion neurale (par exemple, la lésion de la moëlle épinière).
• 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.