(S)-5-(fluoromethyl)pyrrolidin-2-one | 72479-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-5-(fluoromethyl)pyrrolidin-2-one
• 英文别名: (5S)-5-(fluoromethyl)pyrrolidin-2-one
• CAS: 72479-03-9
• 化学式: C₅H₈FNO
• mdl: MFCD16990739
• 分子量: 117.123
• InChiKey: WQNMHLGUIXQTED-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-5-(fluoromethyl)pyrrolidin-2-one 在 盐酸 作用下， 反应 6.0h， 以95%的产率得到(S)-(+)-4-Amino-5-fluoropentanoic Acid Hydrochloride
  参考文献：
  名称：

  Syntheses of (S)-5-substituted 4-aminopentanoic acids: a new class of .gamma.-aminobutyric acid transaminase inactivators

  摘要：

  DOI：

  10.1021/jo01293a011
• 作为产物：
  描述：

  L-焦谷氨酸甲酯 在 sodium tetrahydroborate 、 四溴化碳 、 silver fluoride 、 三苯基膦 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 (S)-5-(fluoromethyl)pyrrolidin-2-one
  参考文献：
  名称：

  The fluorine-NHC gauche effect: a structural and computational study

  摘要：

  Herein, we report the synthesis and X-ray structural analysis of a collection of fluorinated metal N-heterocyclic carbenes (Ag, Au, Pd, Rh, Ir) and their precursor salts. The common structural feature of these species is a flanking fluoroethyl group, which is either freely rotating or embedded within a bicyclic framework. Solid state analysis confirmed a gauche conformational preference in all cases with the fluorine adopting a syn clinal arrangement (phi([NCCF])similar to 60 degrees) with respect to the triazolium nitrogen at the vicinal position of the NHC. A density functional theory analysis was employed to quantify these effects and evaluate the influence of electronic modulation of the carbenic carbon [(C=N+); neutral carbene (C:); metal-bound carbene (C=M)], on the relative gauche/anti preference, thus highlighting the potential of this conformational phenomenon as a useful molecular design strategy for controlling the topology of organometallic complexes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.071

文献信息

• [EN] TETRACYCLINE ANALOGS<br/>[FR] ANALOGUES DE TÉTRACYCLINE
  申请人：TETRAPHASE PHARMACEUTICALS INC

  公开号：WO2012021712A1

  公开（公告）日：2012-02-16

  The present invention is directed to a compound represented by Structural Formula (I), or a pharmaceutically acceptable salt thereof. The variables for Structural Formula (I) are defined herein. Also described is a pharmaceutical composition comprising the compound of Structural Formula (I) and its therapeutic use.

  本发明涉及一种由结构式(I)表示的化合物，或其药用可接受的盐。结构式(I)的变量在此定义。还描述了一种包括结构式(I)化合物及其治疗用途的药物组合物。
• AMIDE DERIVATIVE INHIBITOR AND PREPARATION METHOD AND APPLICATION THEREOF
  申请人：Jiangsu Hansoh Pharmaceutical Group Co., Ltd.

  公开号：EP3590931A1

  公开（公告）日：2020-01-08

  An amide derivative inhibitor and a preparation method and an application thereof. Specifically relating to the compound shown in general formula (I), a preparation method for same, a pharmaceutical composition comprising said compound, and an application of same as an ASK inhibitor for the treatment of neurodegenerative disease, cardiovascular disease, inflammation, autoimmune and metabolic disease, each of the substituents in the general formula (I) being as defined in the description.

  一种酰胺衍生物抑制剂及其制备方法和应用。具体涉及到一般式(I)所示的化合物，其制备方法，包含该化合物的药物组合物，以及将其作为ASK抑制剂用于治疗神经退行性疾病、心血管疾病、炎症、自身免疫和代谢疾病的应用，一般式(I)中的每个取代基如描述中所定义。
• SILVERMAN R. B.; LEVY M. A., J. ORG. CHEM., 1980, 45, NO 5, 815-818
  作者：SILVERMAN R. B.、 LEVY M. A.

  DOI：——

  日期：——
• The fluorine-NHC gauche effect: a structural and computational study
  作者：Susann Paul、W. Bernd Schweizer、Graham Rugg、Hans Martin Senn、Ryan Gilmour

  DOI：10.1016/j.tet.2013.02.071

  日期：2013.7

  Herein, we report the synthesis and X-ray structural analysis of a collection of fluorinated metal N-heterocyclic carbenes (Ag, Au, Pd, Rh, Ir) and their precursor salts. The common structural feature of these species is a flanking fluoroethyl group, which is either freely rotating or embedded within a bicyclic framework. Solid state analysis confirmed a gauche conformational preference in all cases with the fluorine adopting a syn clinal arrangement (phi([NCCF])similar to 60 degrees) with respect to the triazolium nitrogen at the vicinal position of the NHC. A density functional theory analysis was employed to quantify these effects and evaluate the influence of electronic modulation of the carbenic carbon [(C=N+); neutral carbene (C:); metal-bound carbene (C=M)], on the relative gauche/anti preference, thus highlighting the potential of this conformational phenomenon as a useful molecular design strategy for controlling the topology of organometallic complexes. (C) 2013 Elsevier Ltd. All rights reserved.
• Syntheses of (S)-5-substituted 4-aminopentanoic acids: a new class of .gamma.-aminobutyric acid transaminase inactivators
  作者：Richard B. Silverman、Mark A. Levy

  DOI：10.1021/jo01293a011

  日期：1980.2