5-(2,2-dimethyl)propyloxy-2-pyrrolidinone | 119984-41-7

• 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-(2,2-dimethyl)propyloxy-2-pyrrolidinone
• 英文别名: 5-neopentyloxy pyrrolidin-2-one；5-(2,2-dimethylpropoxy)pyrrolidin-2-one
• CAS: 119984-41-7
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: XPTYFBYDLJXYEY-UHFFFAOYSA-N

物化性质

• 沸点：
  298.3±33.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  苯甲酰氯 、 5-(2,2-dimethyl)propyloxy-2-pyrrolidinone 在 正丁基锂 作用下， 生成 1-benzoyl 5-neopentyloxy 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-乙氧基-2-吡咯烷酮 、 新戊醇 在 新戊醇 、 Hg 、 正己烷 作用下， 反应 4.25h， 以3.2 g of the expected product is obtained的产率得到5-(2,2-dimethyl)propyloxy-2-pyrrolidinone
  参考文献：
  名称：

  Derivatives of 1-benzoyl 2-oxo 5-alkoxy pyrrolidine, their preparation,

  摘要：

  本发明涉及一种治疗智力或神经衰弱、记忆力减退、衰老或精神紧张的化合物，其化学式为（I）：##STR1##其中R'表示氢、含有多达12个碳原子的线性、支链或环烷基、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，R代表含有多达14个碳原子的芳基（可选取代）或单环或多环的杂环芳基基团（可选取代）；还包括含有这些化合物的治疗组合物和使用方法。

  公开号：

  US04948804A1

文献信息

• Dérivés de la 1-benzoyl 2-oxo 5-alcoxy pyrrolidine, leur préparation, leur application comme médicament et les compositions les renfermant
  申请人：ROUSSEL-UCLAF

  公开号：EP0296979A2

  公开（公告）日：1988-12-28

  L'invention a pour objet les composés de formule (I) : dans laquelle R′ représente un atome d'hydrogène, un radical alcoyle, linéaire, ramifié ou cyclique renfermant jusqu'à 12 atomes de carbone, un radical alcényle renfermant de 2 à 8 atomes de carbone, un radical acyle renfermant de 1 à 6 atomes de carbone ou un radical aralcoyle renfermant de 7 à 15 atomes de carbone et R représente un radical aryle renfermant jusqu'à 14 atomes de carbone éventuellement subtitué ou un radical hétérocyclique aromatique mono ou polycyclique éventuellement substitué, leur préparation, leur application comme médicaments et les compositions les renfermant.

  本发明的目的是式(I)化合物： 其中 R′代表氢原子、含最多 12 个碳原子的直链、支链或环状烷基、含 2 至 8 个碳原子的烯基、含 1 至 6 个碳原子的酰基或含 7 至 15 个碳原子的芳基，R 代表任选取代的芳基、含有 1 至 6 个碳原子的酰基或含有 7 至 15 个碳原子的芳烷基，R 代表含有最多 14 个碳原子的任选取代的芳基或任选取代的单环或多环芳香杂环基。
• US4948804A
  申请人：——

  公开号：US4948804A

  公开（公告）日：1990-08-14
• Derivatives of 1-benzoyl 2-oxo 5-alkoxy pyrrolidine, their preparation,
  申请人：Roussel Uclaf

  公开号：US04948804A1

  公开（公告）日：1990-08-14

  Compounds useful in the treatment of patients suffering from intellectual or nervous asthenias, memory failures, senescence or mental 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, optionally substituted, or a mono- or polycryclic heterocyclic aromatic radical, optionally substituted; also therapeutic compositions containing those compounds and method of use.

  用于治疗智力或神经衰弱、记忆丧失、衰老或精神紧张患者的化合物，其公式为(I)：##STR1## 其中R'代表氢、线型、支链或环烷基，含有最多12个碳原子，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个碳原子的芳烷基；R代表含有最多14个碳原子的芳基，可选地被取代，或者是一个单环或多环的杂环芳基，可选地被取代；还包括含有这些化合物的治疗组合物及其使用方法。
• 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.