5-n-decyloxy-2-pyrrolidinone | 119984-62-2

• 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: 5-n-decyloxy-2-pyrrolidinone
• 英文别名: 5-n-decyloxy-pyrrolidin-2-one；5-decoxypyrrolidin-2-one
• CAS: 119984-62-2
• 化学式: C₁₄H₂₇NO₂
• 分子量: 241.374
• InChiKey: TYYNDOIJBZEHKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 5-n-decyloxy-2-pyrrolidinone 在 氢氧化钾 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以73%的产率得到1-Benzyl-5-decyloxy-pyrrolidin-2-one
  参考文献：
  名称：

  Amnesia-reversal activity of a series of 5-alkoxy-1-arylcarbonyl-2-pyrrolidinones and 5-alkoxy-1-arylmethyl-2-pyrrolidinones

  摘要：

  A series of 5-alkoxy-1-arylcarbonyl-2-pyrrolidinones (1-27) were prepared by condensation of arylcarbonyl chlorides with 5-alkoxy-2 pyrrolidinones in the presence of butyl lithium in tetrahydrofuran. Alkylation of these intermediates with substituted benzyl bromides or chlorides, under solid/liquid phase-transfer conditions (KOH/Bu4NBr) in tetrahydrofuran, yielded 5-alkoxy-1-arylmethyl-2-pyrrolidinones (28-48). In the first series, the compounds with a 5-n-pentyloxy group had maximal ECS-induced amnesia reversing activity in mice, and in the second series, those with a 5-n-octyloxy group. In both series, substitutions on the phenyl ring had detrimental effects. The two most promising compounds 1-benzoyl-5-n-pentyloxy-2-pyrrolidinone (14) and 1-benzyl-5-n-octyloxy-2-pyrrolidinone (37) were more potent than piracetam and aniracetam and active over broader dose ranges: 50-200 and 50-400 mg/kg, po. Both compounds also reversed scopolamine-induced amnesia in mice, from 50 to 400 mg/kg, po (14) and from 100 to 400 mg/kg, po (37). Finally, 37 showed remarkable activity in protecting the mouse brain against chemically induced hypoxia, with a minimal effective dose of 50 mg/kg, ip, or 100 mg/kg, ip, in NaNO2- or KCN-induced hypoxia.

  DOI：

  10.1016/0223-5234(91)90102-s
• 作为产物：
  描述：

  5-羟基-2-吡咯烷酮 、 癸醇 在 120H 作用下， -10.0~60.0 ℃ 、7.11 kPa 条件下， 反应 27.0h， 以3.5 g of the expected product is obtained的产率得到5-n-decyloxy-2-pyrrolidinone
  参考文献：
  名称：

  Derivatives of 1-benzyl-2-oxo-5-alkoxy-pyrrolidine, and medicament

  摘要：

  本发明涉及一种用于治疗患有智力或神经虚弱症、记忆力减退、衰老或心理应力的化合物，其化学式为（I）##STR1##其中R'代表氢、线性、支链或含有高达12个碳原子的环烷基，含有2至8个碳原子的烯基，含有1至6个碳原子的酰基或含有7至15个碳原子的芳基烷基，而R代表含有高达14个碳原子的芳基，可能被取代，或可能被取代的单环或多环杂环芳基基团，但如果R为未取代的苯基，则R'不代表甲基或乙基；还包括含有这些化合物的治疗组合物和使用方法。

  公开号：

  US04882350A1

文献信息

• Nouveaux dérivés de 1-benzyl 2-oxo 5-alcoxy pyrrolidine, leur procédé de préparation, leur application comme médicaments et les compositions les renfermant
  申请人：ROUSSEL-UCLAF

  公开号：EP0296978B1

  公开（公告）日：1991-09-11
• US4882350A
  申请人：——

  公开号：US4882350A

  公开（公告）日：1989-11-21
• Amnesia-reversal activity of a series of 5-alkoxy-1-arylcarbonyl-2-pyrrolidinones and 5-alkoxy-1-arylmethyl-2-pyrrolidinones
  作者：E Toja、C Gorini、C Zirotti、F Barzaghi、G Galliani

  DOI：10.1016/0223-5234(91)90102-s

  日期：1991.6

  A series of 5-alkoxy-1-arylcarbonyl-2-pyrrolidinones (1-27) were prepared by condensation of arylcarbonyl chlorides with 5-alkoxy-2 pyrrolidinones in the presence of butyl lithium in tetrahydrofuran. Alkylation of these intermediates with substituted benzyl bromides or chlorides, under solid/liquid phase-transfer conditions (KOH/Bu4NBr) in tetrahydrofuran, yielded 5-alkoxy-1-arylmethyl-2-pyrrolidinones (28-48). In the first series, the compounds with a 5-n-pentyloxy group had maximal ECS-induced amnesia reversing activity in mice, and in the second series, those with a 5-n-octyloxy group. In both series, substitutions on the phenyl ring had detrimental effects. The two most promising compounds 1-benzoyl-5-n-pentyloxy-2-pyrrolidinone (14) and 1-benzyl-5-n-octyloxy-2-pyrrolidinone (37) were more potent than piracetam and aniracetam and active over broader dose ranges: 50-200 and 50-400 mg/kg, po. Both compounds also reversed scopolamine-induced amnesia in mice, from 50 to 400 mg/kg, po (14) and from 100 to 400 mg/kg, po (37). Finally, 37 showed remarkable activity in protecting the mouse brain against chemically induced hypoxia, with a minimal effective dose of 50 mg/kg, ip, or 100 mg/kg, ip, in NaNO2- or KCN-induced hypoxia.
• Derivatives of 1-benzyl-2-oxo-5-alkoxy-pyrrolidine, and medicament
  申请人：Roussel Uclaf

  公开号：US04882350A1

  公开（公告）日：1989-11-21

  Compounds useful in the treatment of patients suffering from intellectual or nervous asthenias, memory failures, senescence or metal strain of the formula (I) ##STR1## in which R' represents hydrogen, linear, branched or cyclic alkyl containing up to 12 carbon atoms, alkenyl containing from 2 to 8 carbon atoms, acyl containing from 1 to 6 carbon atoms or aralkyl containing from 7 to 15 carbon atoms and R represents aryl containing up to 14 carbon atoms, possibly substituted, or a mono- or polycyclic heterocyclic aromatic radical possibly substituted, provided that if R is unsubstituted phenyl, R' does not represent methyl or ethyl; also therapeutic compositions containing those compounds and method of use.

  本发明涉及一种用于治疗患有智力或神经虚弱症、记忆力减退、衰老或心理应力的化合物，其化学式为（I）##STR1##其中R'代表氢、线性、支链或含有高达12个碳原子的环烷基，含有2至8个碳原子的烯基，含有1至6个碳原子的酰基或含有7至15个碳原子的芳基烷基，而R代表含有高达14个碳原子的芳基，可能被取代，或可能被取代的单环或多环杂环芳基基团，但如果R为未取代的苯基，则R'不代表甲基或乙基；还包括含有这些化合物的治疗组合物和使用方法。