4-acetoxy-2-pyrrolidinone | 64097-45-6

• 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: 4-acetoxy-2-pyrrolidinone
• 英文别名: 4-acetoxy-2-pyrrolidone；4-acetoxy-pyrrolidin-2-one；5-oxo-3-pyrrolidinyl acetate；4-Acetoxy-2-pyrrolidinon；(+-)-4-(Acetyloxy)-2-pyrrolidinone；(5-oxopyrrolidin-3-yl) acetate
• CAS: 64097-45-6
• 化学式: C₆H₉NO₃
• mdl: MFCD01687422
• 分子量: 143.142
• InChiKey: KKACRYNIWXDYAE-UHFFFAOYSA-N

物化性质

• 熔点：
  88-90 °C(Solv: isopropanol (67-63-0))
• 沸点：
  304.7±35.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-acetoxy-2-pyrrolidinone 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 六甲基磷酰三胺 、 paraffin 为溶剂， 反应 4.0h， 以50%的产率得到ethyl (4-acetoxy-2-oxopyrrolidin-1-yl)acetate
  参考文献：
  名称：

  Pellegata; Pinza; Pifferi, Farmaco, Edizione Scientifica, 1981, vol. 36, # 10, p. 845 - 855

  摘要：

  DOI：
• 作为产物：
  描述：

  4-acetamido-3-hydroxybutyramide 在 盐酸 作用下， 以 水 为溶剂， 以87%的产率得到4-acetoxy-2-pyrrolidinone
  参考文献：
  名称：

  Structure elucidation of pantherine, a flycidal alkaloid from Amanita pantherina (DC.) Fr.

  摘要：

  通过光谱实验及与合成化合物的化学关联，鉴定出Pantherine为5-氨基甲基-3-羟基异恶唑。

  DOI：

  10.1248/cpb.33.1083

文献信息

• Lipase-Catalyzed Practical Synthesis of (<i>R</i>)-1-Benzyl-3-hydroxy-2,5-pyrrolidinedione and Its Related Compounds
  作者：Hiroshi Tomori、Kuniko Shibutani、Katsuyuki Ogura

  DOI：10.1246/bcsj.69.207

  日期：1996.1

  investigated by the use of the enzymatic hydrolysis of its acetate (2a). Among several hydrolases examined here, lipase PS from Pseudomonas cepaciagave the best result: In a mixed solvent (1 : 1 v/v) of dioxane and a phosphate buffer (pH 7), the hydrolysis took place smoothly with a high enantioselectivity (E > 3000). Several 3-alkanoyl derivatives of 1 were subjected to the lipase PS-catalyzed hydrolysis

  通过使用其乙酸酯 (2a) 的酶促水解，研究了制备 (R)-1-苄基-3-羟基-2,5-吡咯烷二酮 (1) 的实用方法。在这里检测的几种水解酶中，洋葱假单胞菌的脂肪酶 PS 的结果最好：在二恶烷和磷酸盐缓冲液 (pH 7) 的混合溶剂 (1:1 v/v) 中，水解以高对映选择性 (E > 3000）。1 的几种 3-烷酰基衍生物经过脂肪酶 PS 催化水解。烷酰基的链长不会显着影响反应速率或对映选择性。相比之下，1-苯甲酰基衍生物的水解缓慢进行，对映选择性低（E = 19）。
• 1-(P-Methoxy p-hydroxy, and p-benzyloxy benzoyl)-2-pyrrolidinones
  申请人：Hoffmann-La Roche Inc.

  公开号：US04369139A1

  公开（公告）日：1983-01-18

  1-(p-methoxybenzoyl)-2-pyrrolidinone and intermediates useful in its preparation are described. The 1-(p-methoxybenzoyl)-2-pyrrolidinone is useful in the prevention of cerebral insufficiency.

  本文描述了1-(对甲氧基苯甲酰基)-2-吡咯烷酮及其制备中间体。1-(对甲氧基苯甲酰基)-2-吡咯烷酮可用于预防脑功能不足。
• N-Tert-Butoxycarbonyl-2-Pyrrolidinones and Production Method Thereof
  申请人：Hirata Norihiko

  公开号：US20100280259A1

  公开（公告）日：2010-11-04

  N-tert-butoxycarbonyl-2-pyrrolidinones represented by the following formula (1). In the formula (1), R1, R2, R3, R4, R5 and R6 independently represent a hydrogen atom, a halogen atom, a cyano group, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, which may have a substituent, a linear, branched or cyclic alkenyl group having 2 to 10 carbon atoms, which may have a substituent, or the like, R1 and R2 may be linked to form a >C═O group along with the carbon atom to which both are attached, R3 and R4 may be linked to form a >C═O group along with the carbon atom to which both are attached, R5 and R6 may be linked to form a >C═O group along with the carbon atom to which both are attached, or any two among R1, R2, R3, R4, R5 and R6 may be linked to form a polymethylene group having 1 to 4 carbon atoms which may have a substituent.

  以下公式（1）表示N-tert-丁氧羰基-2-吡咯酮。在公式（1）中，R1，R2，R3，R4，R5和R6独立地表示氢原子，卤素原子，氰基，具有1到10个碳原子的线性，支链或环状烷基，可以具有取代基，具有2到10个碳原子的线性，支链或环状烯基，可以具有取代基，或类似物，R1和R2可以连接形成>C═O基团，同时与它们附着的碳原子，R3和R4可以连接形成>C═O基团，同时与它们附着的碳原子，R5和R6可以连接形成>C═O基团，同时与它们附着的碳原子，或者R1，R2，R3，R4，R5和R6中的任意两个可以连接形成具有1到4个碳原子的聚亚甲基基团，可以具有取代基。
• N-TERT-BUTOXYCARBONYL-2-PYRROLIDINONES AND PRODUCTION METHOD THEREOF
  申请人：Hirata Norihiko

  公开号：US20090163722A1

  公开（公告）日：2009-06-25

  N-tert-butoxycarbonyl-2-pyrrolidinones represented by the following formula (1). In the formula (1), R1, R2, R3, R4, R5 and R6 independently represent a hydrogen atom, a halogen atom, a cyano group, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, which may have a substituent, a linear, branched or cyclic alkenyl group having 2 to 10 carbon atoms, which may have a substituent, or the like, R1 and R2 may be linked to form a >C═O group along with the carbon atom to which both are attached, R3 and R4 may be linked to form a >C═O group along with the carbon atom to which both are attached, R5 and R6 may be linked to form a >C═O group along with the carbon atom to which both are attached, or any two among R1, R2, R3, R4, R5 and R6 may be linked to form a polymethylene group having 1 to 4 carbon atoms which may have a substituent.

  下列化学式（1）代表的是N-叔丁氧羰基-2-吡咯酮。 在化学式（1）中，R1、R2、R3、R4、R5和R6各自独立地代表氢原子、卤素原子、氰基、具有1到10个碳原子的直链、支链或环状烷基，可能具有取代基，具有2到10个碳原子的直链、支链或环状烯基，可能具有取代基，或者类似物。R1和R2可以连接形成>C═O基团，同时与两者连接的碳原子相连。R3和R4可以连接形成>C═O基团，同时与两者连接的碳原子相连。R5和R6可以连接形成>C═O基团，同时与两者连接的碳原子相连。或者，在R1、R2、R3、R4、R5和R6中的任意两个可以连接形成具有1到4个碳原子的聚亚甲基基团，可能具有取代基。
• Chemical compounds
  申请人：ISF SOCIETA PER AZIONI

  公开号：EP0207680A2

  公开（公告）日：1987-01-07

  Compounds of Structure (1): in which R' is H, C1-5 alkyl (straight or branched), or phenyl; W is a bond, -NHC.HR6CO- or -NHCHR6CONH-CHR7CO-, where R6 and R7, which can be the same or different are H or C1-6 alkyl (straight or branched); R2 is H, C1-5 alkyl (straight or branched), aryl or a benzyl group optionally substituted by C1-5 alkyl (straight or branched), C1-4, alkoxy (straight or branched) or hydroxy; R3 and R4, which can be the same or different, are H, C1-5 alkyl (straight or branched) or phenyl, or R3 and R4 can together form a 1,4-butylene or 1,5-pentylene group; R6 is H or -CHR8CONR9R10, where R8, R9 and R'°, which can be the same or different, are H or C1-5 alkyl (straight or branched); R" and R12, which can be the same or different, are H, C1-5 alkyl (straight or branched), or acyl or together with the nitrogen atom shown form a 2-oxo-pyrrolidino group optionally substituted in the 4-position by a hydroxy or C1-5 (straight or branched) alkoxy group, or a 5-oxo-1-imidazolidine group optionally substituted at the 2- position by one or two C1-5 alkyl groups or a 1,4-butylene or 1,5-pentylene group, or optionally substituted at the 4-position by C1-5 alkyl, or a pharmaceutically acceptable salt thereof, processes and intermediates for making them, pharmaceutical compositions containing them and their use as nootropic agents.

  结构 (1) 的化合物： 其中 R' 是 H、C1-5 烷基（直链或支链）或苯基； W 是键、-NHC.HR6CO- 或 -NHCHR6CONH-CHR7CO-，其中 R6 和 R7（可以相同或不同）是 H 或 C1-6 烷基（直链或支链）； R2 是 H、C1-5 烷基（直链或支链）、芳基或任选被 C1-5 烷基（直链或支链）、C1-4、烷氧基（直链或支链）或羟基取代的苄基； R3 和 R4（可以相同或不同）是 H、C1-5 烷基（直链或支链）或苯基，或 R3 和 R4 可共同形成 1，4-丁烯或 1，5-戊烯基团； R6 是 H 或 -CHR8CONR9R10，其中 R8、R9 和 R'° 可以相同或不同，是 H 或 C1-5 烷基（直链或支链）； R "和 R12（可以相同或不同）是 H、C1-5 烷基（直链或支链）或酰基，或与所示的氮原子一起形成 2-氧代吡咯烷基，可选择在 4 位被羟基或 C1-5（直链或支链）烷氧基取代、或 5-氧代-1-咪唑烷基，可选择在 2-位被一个或两个 C1-5 烷基或 1,4-丁烯或 1,5-戊烯基取代，或可选择在 4-位被 C1-5 烷基取代，或其药学上可接受的盐、制造它们的工艺和中间体、含有它们的药物组合物，以及它们作为促智剂的用途。