3-(2,2,2-三氟乙酰基)四氢吡喃-4-酮 | 158351-87-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(2,2,2-三氟乙酰基)四氢吡喃-4-酮
• 英文名称: 3-(trifluoroacetyl)tetrahydro-4H-pyran-4-one
• 英文别名: 3-(Trifluoroacetyl)oxan-4-one；3-(2,2,2-trifluoroacetyl)oxan-4-one
• CAS: 158351-87-2
• 化学式: C₇H₇F₃O₃
• 分子量: 196.126
• InChiKey: GHXRMWZXTQUELM-UHFFFAOYSA-N

物化性质

• 沸点：
  230.2±40.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(2,2,2-三氟乙酰基)四氢吡喃-4-酮 在 copper(I) oxide 、 N,N-二甲基甘氨酸 、 caesium carbonate 、 一水合肼 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 13.0h， 生成 1-({2,6-difluoro-4-[3-(trifluoromethyl)-6,7-dihydropyrano[4,3-c]pyrazol-1(4H)-yl]phenyl}methyl)-2-pyrrolidinone
  参考文献：
  名称：

  Integration of Lead Optimization with Crystallography for a Membrane-Bound Ion Channel Target: Discovery of a New Class of AMPA Receptor Positive Allosteric Modulators

  摘要：

  A novel series of AMPAR positive modulators is described that were identified by high throughput screening. The molecules of the series have been optimized from a high quality starting point hit to afford excellent developability, tolerability, and efficacy profiles, leading to identification of a clinical candidate. Unusually for an ion channel target, this optimization was integrated with regular generation of ligand-bound crystal structures and uncovered a novel chemotype with a unique and highly conserved mode of interaction via a trifluoromethyl group.

  DOI：

  10.1021/jm100679e
• 作为产物：
  描述：

  四氢吡喃酮 、 三氟乙酸乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到3-(2,2,2-三氟乙酰基)四氢吡喃-4-酮
  参考文献：
  名称：

  COMPOUNDS WHICH POTENTIATE AMPA RECEPTOR AND USES THEREOF IN MEDICINE

  摘要：

  提供式(I)的化合物，以及其盐和溶剂合物：还公开了制备过程、药物组合物以及将其用作药物的用途，例如用于治疗由谷氨酸受体功能减少或失衡引起的疾病或症状，如精神分裂症或认知障碍。

  公开号：

  US20100137276A1

文献信息

• [EN] COMPOUNDS WHICH POTENTIATE AMPA RECEPTOR AND USES THEREOF IN MEDICINE<br/>[FR] COMPOSÉS QUI POTENTIALISENT LE RÉCEPTEUR AMPA ET LEURS UTILISATIONS EN MÉDECINE
  申请人：GLAXO GROUP LTD

  公开号：WO2009053448A1

  公开（公告）日：2009-04-30

  The invention provides compounds of formula (I) and salts thereof wherein R1, R2, R3, R4 and X are as defined in the description. Processes for preparation, pharmaceutical compositions, and uses thereof as a medicament, for example in the treatment of a disease or condition mediated by a reduction or imbalance in glutamate receptor function, such as schizophrenia or cognition impairment, are also disclosed.

  该发明提供了式（I）的化合物及其盐，其中R1、R2、R3、R4和X如描述中所定义。还公开了制备方法、药物组合物以及将其用作药物的用途，例如在治疗由谷氨酸受体功能减少或失衡介导的疾病或症状，如精神分裂症或认知障碍。
• PYRIMIDINE DERIVATIVE
  申请人：NIPPON SODA CO., LTD.

  公开号：EP0665224A1

  公开（公告）日：1995-08-02

  A compound represented by general formula (I) and excellent in herbicidal and agrohorticultural antibacterial activities, wherein R¹ and R² represent each hydrogen, alkyl, etc., or alternatively they may be combined together to represent oxo, thioxo, etc., or a spiro ring selected from among (a), (b), etc.; R³ and R⁵ represent each hydrogen, halogen, alkyl, etc., and R⁴ represents hydrogen, halogen, amino, etc., provided that R³ and R⁵ are different from each other when R⁴ is hydrogen and that R⁴ may be combined with R³ or R⁵ and the pyrimidine ring to represent a condensed ring represented by (c) or (d); R⁶ and R⁷ represent each hydrogen, halogen, alkyl, etc., provided that the case wherein both R⁶ and R⁷ represent hydrogen is excluded; R⁸ represents halogen, alkyl, etc.; and n represents 0, 1, 2 or 3; provided that when both R¹ and R² represent hydrogen, then R⁴ is combined with R³ or R⁵ and the pyrimidine group to represent the above condensed ring.

  一种由通式(I)表示并具有优异除草和农用园艺抗菌活性的化合物，其中 R¹ 和 R² 各自代表氢、烷基等，或者它们可以组合在一起代表氧代、硫代等，或者代表选自(a)、(b)等的螺环；R³ 和 R⁵ 各自代表氢、卤素、烷基等，R⁴ 代表氢、卤素、氨基等、当 R⁴ 为氢时，R³ 和 R⁵ 互不相同，且 R⁴ 可与 R³ 或 R⁵ 以及嘧啶环结合，以表示由 (c) 或 (d) 所代表的缩合环；R⁶ 和 R⁷ 各自代表氢、卤素、烷基等、R⁶ 和 R⁷ 分别代表氢、卤素、烷基等，但不包括 R⁶ 和 R⁷ 都代表氢的情况；R⁸ 代表卤素、烷基等；n 代表 0、1、2 或 3；但当 R¹ 和 R² 都代表氢时，R⁴ 与 R³ 或 R⁵ 和嘧啶基结合代表上述缩合环。
• WO2008/113795
  申请人：——

  公开号：——

  公开（公告）日：——
• Fused 3-Hydroxy-3-trifluoromethylpyrazoles Inhibit Mutant Huntingtin Toxicity
  作者：Salvatore La Rosa、Tiziana Benicchi、Laura Bettinetti、Ilaria Ceccarelli、Enrica Diodato、Cesare Federico、Pasquale Fiengo、Davide Franceschini、Ozgun Gokce、Freddy Heitz、Giulia Lazzeroni、Ruth Luthi-Carter、Letizia Magnoni、Vincenzo Miragliotta、Carla Scali、Michela Valacchi

  DOI：10.1021/ml400251g

  日期：2013.10.10

  Here, we describe the selection and optimization of a chemical series active in both a full-length and a fragment-based Huntington's disease (HD) assay. Twenty-four thousand small molecules were screened in a phenotypic HD assay, identifying a series of compounds bearing a 3-hydroxy-3-trifluoromethylpyrazole moiety as able to revert the toxicity induced by full-length mutant Htt by up to 50%. A chemical exploration around the series led to the identification of compound 4f, which demonstrated to be active in a Htt171-82Qrat primary striatal neuron assay and a PC12-Exon-1 based assay. This compound was selected for testing in R6/2 mice, in which it was well-tolerated and showed a positive effect on body weight and a positive trend in preventing ventricular volume enlargment. These studies provide strong rationale for further testing the potential benefits of 3-hydroxy-3-trifluoromethylpyrazoles in treating HD.
• [EN] COMPOUNDS WHICH POTENTIATE AMPA RECEPTOR AND USES THEREOF IN MEDICINE<br/>[FR] COMPOSÉS DE POTENTIALISATION DU RÉCEPTEUR AMPA ET UTILISATIONS EN MÉDECINE
  申请人：GLAXO GROUP LTD

  公开号：WO2008053031A1

  公开（公告）日：2008-05-08

  [EN] Compounds of formula (I), and salts and solvates thereof are provided. Processes for preparation, pharmaceutical compositions, and uses thereof as a medicament, for example in the treatment of a disease or condition mediated by a reduction or imbalance in glutamate receptor function, such as schizophrenia or cognition impairment, are also disclosed.
  [FR] La présente invention concerne des composés de formule (I), leurs sels et leurs solvates. L'invention concerne également des procédés de préparation, des compositions pharmaceutiques, et leurs utilisations en tant que médicament, par exemple dans le traitement d'une maladie ou d'une affection induite par une réduction ou un déséquilibre de la fonction du récepteur du glutamate, telle que la schizophrénie ou un trouble cognitif.