1,1,1,3-tetrafluoro-heptadecan-2-one | 1071001-36-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1,1,3-tetrafluoro-heptadecan-2-one
• 英文别名: 1,1,1,3-tetrafluoro-2-heptadecanone；1,1,1,3-Tetrafluoroheptadecan-2-one
• CAS: 1071001-36-9
• 化学式: C₁₇H₃₀F₄O
• 分子量: 326.418
• InChiKey: HCIDRHZIAMIVIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,1,1,3-tetrafluoroheptadecane-2,2-diol 在 (三氟甲基)三甲基硅烷 、 cesium fluoride 、 盐酸 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 36.5h， 以58%的产率得到1,1,1,3-tetrafluoro-heptadecan-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

• 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）。
• [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).