3,3-二氟-5-(羟甲基)-(5S)-2-吡咯烷酮 | 255903-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 3,3-二氟-5-(羟甲基)-(5S)-2-吡咯烷酮
• 英文名称: (5S)-3,3-difluoro-5-hydroxymethyl-2-pyrrolidinone
• 英文别名: (S)-3,3-Difluoro-5-(hydroxymethyl)pyrrolidin-2-one；(5S)-3,3-difluoro-5-(hydroxymethyl)pyrrolidin-2-one
• CAS: 255903-84-5
• 化学式: C₅H₇F₂NO₂
• 分子量: 151.113
• InChiKey: CMRXZAKSZIVSCC-VKHMYHEASA-N

物化性质

• 沸点：
  304.1±42.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3,3-二氟-5-(羟甲基)-(5S)-2-吡咯烷酮 在 咪唑 、 4-二甲氨基吡啶 、 N,O-双三甲硅基乙酰胺 、 三乙基硼氢化锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  Synthesis, evaluation of anti-HIV-1 and anti-HCV activity of novel 2′,3′-dideoxy-2′,2′-difluoro-4′-azanucleosides

  摘要：

  A series of 2',3'-dideoxy-2',2'-difluoro-4'-azanucleosides of both pyrimidine and purine nucleobases were synthesized in an efficient manner starting from commercially available L-pyroglutamic acid via glycosylation of difluorinated pyrrolidine derivative 15. Several 4'-azanucleosides were prepared as a separable mixture of alpha- and beta-anomers. The 6-chloropurine analogue was obtained as a mixture of N-7 and N-9 regioisomers and their structures were identified based on NOESY and HMBC spectral data. Among the 4'-azanucleosides tested as HIV-1 inhibitors in primary human lymphocytes, four compounds showed modest activity and the 5-fluorouracil analogue (18d) was found to be the most active compound (EC50 = 36.9 mu M) in this series. None of the compounds synthesized in this study demonstrated anti-HCV activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.026
• 作为产物：
  描述：

  (5S)-2,2-dimethyl-7,7-difluoro-8-oxo-1-aza-3-oxa-bicyclo[3.3.0]octane 在 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 16.0h， 生成 3,3-二氟-5-(羟甲基)-(5S)-2-吡咯烷酮
  参考文献：
  名称：

  [EN] FUSED BICYCLIC PYRAZOLE DERIVATIVES AND METHODS OF USE THEREOF FOR THE TREATMENT OF HERPESVIRUSES
  [FR] DÉRIVÉS BICYCLIQUES FUSIONNÉS DE PYRAZOLE ET LEURS MÉTHODES D'UTILISATION POUR LE TRAITEMENT DE VIRUS HERPÉTIQUES

  摘要：

  本发明涉及式(I)的新型融合双环吡唑衍生物及其药学上可接受的盐，其中R1、R2、R3、R4、R5和R6如本文所定义。本发明还涉及包含至少一种融合双环吡唑衍生物的组合物，以及使用融合双环吡唑衍生物治疗或预防患者的疱疹病毒感染的方法。

  公开号：

  WO2022132686A1

文献信息

• Certain chemical entities, compositions, and methods
  申请人：Qian Xiangping

  公开号：US20090275537A1

  公开（公告）日：2009-11-05

  Chemical entities that modulate smooth muscle myosin and/or non-muscle myosin, pharmaceutical compositions and methods of treatment of diseases and conditions associated with smooth muscle myosin and/or non-muscle myosin are described.

  本文描述了调节平滑肌肌球蛋白和/或非肌肉肌球蛋白的化学实体、制药组合物以及治疗与平滑肌肌球蛋白和/或非肌肉肌球蛋白相关的疾病和病状的方法。
• CERTAIN CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS
  申请人：QIAN Xiangping

  公开号：US20120135964A1

  公开（公告）日：2012-05-31

  Chemical entities that modulate smooth muscle myosin and/or non-muscle myosin, pharmaceutical compositions and methods of treatment of diseases and conditions associated with smooth muscle myosin and/or non-muscle myosin are described.

  本文描述了调节平滑肌肌球蛋白和/或非肌肉肌球蛋白的化学实体、制药组合物和治疗与平滑肌肌球蛋白和/或非肌肉肌球蛋白相关的疾病和病状的方法。
• Reactivity Enhancement for Chiral Dirhodium(II) Tetrakis(Carboxamidates)
  作者：Michael P. Doyle、Wenhao Hu、Iain M. Phillips、Christopher J. Moody、Adrian G. Pepper、Alexandra G. Z. Slawin

  DOI：10.1002/1615-4169(20010129)343:1<112::aid-adsc112>3.0.co;2-m

  日期：2001.1.29

  Difluorinated Ligands from azetidinone-4-carboxylates and pyrrolidinone-5-carboxylate have been prepared, substituted onto dirhodium(II), and the reactivities and selectivities of the resulting catalysts have been examined. The fluorinated catalysts exhibit enhanced reactivity towards diazo decomposition but diminished enantioselectivities for cyclopropanation. Selectivity for ylide formation and rearrangement or Si-H insertion is enhanced or similar to that with unfluorinated analogues.
• Synthesis of <scp>l</scp>-4,4-Difluoroglutamic Acid via Electrophilic Difluorination of a Lactam
  作者：David W. Konas、James K. Coward

  DOI：10.1021/ol991150l

  日期：1999.12.1

  An enantiomerically pure bicyclic lactam proved to be an excellent substrate for electrophilic difluorination using N-fluorobenzenesulfonimide. The resulting difluorinated lactam can be easily converted into L-4,4-difluoroglutamic acid. To the best of our knowledge, this is the first example of a synthetically useful electrophilic difluorination of an unactivated lactam.