5-异丙氧基吡咯烷-2-酮 | 111712-02-8

• 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: 5-异丙氧基吡咯烷-2-酮
• 英文名称: 5-isopropyloxy pyrrolidin-2-one
• 英文别名: 5-isopropoxy-2-pyrrolidinone；5-isopropoxy-pyrrolidin-2-one；5-isopropyloxy pyrrolidine-2-one；5-isopropoxy pyrrolidin-2-one；5-propan-2-yloxypyrrolidin-2-one
• CAS: 111712-02-8
• 化学式: C₇H₁₃NO₂
• mdl: MFCD19217369
• 分子量: 143.186
• InChiKey: QAKFPYIAROCGIF-UHFFFAOYSA-N

物化性质

• 沸点：
  278.3±33.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 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：

  3-三氟甲基苯磺酰氯 、 5-异丙氧基吡咯烷-2-酮 在 正丁基锂 作用下， 生成 5-(1-Methylethoxy)-1-((3-(trifluoromethyl)phenyl)sulfonyl)-2-pyrrolidinone
  参考文献：
  名称：

  Amnesia-reversal activity of a series of 5-alkoxy-1-arylsulfonyl-2-pyrrolidinones

  摘要：

  A series of 5-alkoxy-1-arylsulfonyl-2-pyrrolidinones were prepared by condensation of arylsulfonyl chlorides with 5-alkoxy-2-pyrrolidinones. Most compounds reversed electroconvulsive shock-induced amnesia in mice, showing the typical inverted U-shaped dose-response curve. The results for 58 compounds indicate that the potency is maximal when there is a 5-ethoxy group and progressively declines as the ether alkyl chain is either elongated or shortened. Substitution on the phenyl ring or its replacement with heterocyclic rings or its hydrogenation decreases the activity. The most promising compounds, with anti-amnesic properties superior in many respects (greater potency, greater efficacy and broader active dose-range) to those of piracetam and aniracetam were further evaluated for reversing scopolamine-induced amnesia and for their anti-hypoxic activity. 5-Ethoxy-1-phenylsulfonyl-2-pyrrolidinone (1) and 5-(1-methylethoxy)-1-/3-(trifluoromethyl) phenylsulfonyl/-2-pyrrolidinone (41) were selected for further evaluation because of their potent anti-amnesic and/or antihypoxic activity.

  DOI：

  10.1016/0223-5234(91)90101-r
• 作为产物：
  描述：

  丁二酰亚胺 在 盐酸 、 氢氧化钾 、 sodium borohydrid 作用下， 以 异丙醇 为溶剂， 生成 5-异丙氧基吡咯烷-2-酮
  参考文献：
  名称：

  1-styrenesulphonyl-2-oxo-5-hydroxy pyrrolidines and their use for memory

  摘要：

  治疗智力或神经衰弱、记忆力减退或老年以及过度智力疲劳患者的治疗化合物，具有公式(I)：##STR1## 其中R.sub.1代表一个含最多8个碳原子的直链或支链烷基，一个含1到6个碳原子的酰基，或一个含3到6个碳原子的环烷基，R代表一个含最多14个碳原子的芳基，未取代或取代的，或一个未取代或取代的单环或多环杂环基团。还包括含有该化合物的治疗组合物、制备该化合物的方法以及使用方法。

  公开号：

  US04810722A1

文献信息

• 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。
• 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。
• 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。
• 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.
• Dérivés de la 1-benzène sulfonyl 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：EP0229566B1

  公开（公告）日：1992-05-06