4-(苄氧基)吡咯烷-2-酮 | 192942-82-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(苄氧基)吡咯烷-2-酮
• 英文名称: 4-Benzyloxypyrrolidine-2-on
• 英文别名: 4-phenylmethoxypyrrolidin-2-one
• CAS: 192942-82-8；769961-93-5
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: QRSLXQGZVSHEQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  4-(苄氧基)吡咯烷-2-酮 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以78%的产率得到3-苯甲氧基吡咯烷
  参考文献：
  名称：

  Cumyl: A Better N-Protecting Group of α-Diazo Acetamides for Intra­molecular C-H Insertion Reaction and its Application in the Synthesis of ­Pregabalin and 3-Benzyloxy Pyrrolidine

  摘要：

  通过 N-cumyl δ±-重氮乙酰胺的分子内 C-H 插入，以优异的区域选择性高效合成了δ-内酰胺。报告了制备普瑞巴林（总收率 79%）和 3-苄氧基吡咯烷（总收率 21%）的简明路线。

  DOI：

  10.1055/s-2004-829568
• 作为产物：
  描述：

  2-苄氧基乙醇 在 dirhodium tetraacetate N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 三苯基膦 、 三氟乙酸 、 potassium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.25h， 生成 4-(苄氧基)吡咯烷-2-酮
  参考文献：
  名称：

  Cumyl: A Better N-Protecting Group of α-Diazo Acetamides for Intra­molecular C-H Insertion Reaction and its Application in the Synthesis of ­Pregabalin and 3-Benzyloxy Pyrrolidine

  摘要：

  通过 N-cumyl δ±-重氮乙酰胺的分子内 C-H 插入，以优异的区域选择性高效合成了δ-内酰胺。报告了制备普瑞巴林（总收率 79%）和 3-苄氧基吡咯烷（总收率 21%）的简明路线。

  DOI：

  10.1055/s-2004-829568

文献信息

• Process For Production of Aralkyloxypyrrolidine Derivative
  申请人：Takeda Toshihiro

  公开号：US20080306283A1

  公开（公告）日：2008-12-11

  The present invention provides a process for producing a 3-aralkyloxypyrrolidine derivative which is important for production of pharmaceutical products and the like. In the present invention, a N-protected-3-hydroxypyrrolidine is converted into a N-protected-3-aralkyloxypyrrolidine by allowing an aralkyl halide to act in the presence of a base and at least one of a metal halide and a phase-transfer catalyst followed by deprotecting a N-protecting group to convert it to a 3-aralkyloxypyrrolidine derivative and subsequently treating the derivative in a solvent containing a polar solvent, thereby obtaining the 3-aralkyloxypyrrolidine derivative as a crystal. According to the present invention, a 3-aralkyloxypyrrolidine derivative of high purity can be produced conveniently and efficiently on an industrial scale.

  本发明提供了一种生产3-芳基氧基吡咯烷衍生物的方法，该方法对于制药产品的生产等非常重要。在本发明中，将N-保护-3-羟基吡咯烷转化为N-保护-3-芳基氧基吡咯烷，通过在碱和至少一个金属卤化物和相转移催化剂的存在下使芳基卤化物起作用，然后去保护N-保护基，将其转化为3-芳基氧基吡咯烷衍生物，随后在含有极性溶剂的溶剂中处理该衍生物，从而得到3-芳基氧基吡咯烷衍生物的晶体。根据本发明，可以在工业规模上方便高效地生产高纯度的3-芳基氧基吡咯烷衍生物。
• 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。
• Stereospecific Nitrogen Insertion Using Amino Diphenylphosphinates: An Aza-Baeyer–Villiger Rearrangement
  作者：Mike Ong、Marlene Arnold、Alexander W. Walz、Johannes M. Wahl

  DOI：10.1021/acs.orglett.2c02361

  日期：2022.8.26

  Amino diphenylphosphinates, which are commercially available or easily prepared from hydroxylamine, undergo ring expansion of cyclobutanones toward γ-lactams under mild conditions. A reaction pathway profoundly different from the common Beckmann reaction is achieved through the ambivalent character of the aminating agent. Thus, rearrangement occurs from a Criegee-like intermediate prior to the formation

  可商购或容易从羟胺制备的氨基二苯基次膦酸盐在温和条件下经受环丁酮向γ-内酰胺的扩环。通过胺化剂的矛盾特征实现了与常见贝克曼反应截然不同的反应途径。因此，重排从类似 Criegee 的中间体发生在肟物种形成之前，机械实验证实了这一点。基于这一观察，分析了相邻组的迁移能力，发现其与母体 Baeyer-Villiger 反应一致，呈现区域选择性（高达 >99:1 rr）、立体特异性（>99% 对映体特异性）和化学选择性(>99%) 插入过程可能。N-烷基化类似物。
• N-TERT-BUTOXYCARBONYL-2-PYRROLIDINONES AND PROCESS FOR PRODUCING THE SAME
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2008999A1

  公开（公告）日：2008-12-31

  N-tert-butoxycarbonyl-2-pyrrolidinones of the following formula (1): [wherein, R1, R2, R3, R4, R5 and R6 represent each independently a hydrogen atom, halogen atom, cyano group, optionally substituted linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, optionally substituted linear, branched or cyclic alkenyl group having 2 to 10 carbon atoms, optionally substituted aryl group having 6 to 20 carbon atoms, optionally substituted amino group, -ORa group, or -SRb group, Ra and Rb represent each independently a hydrogen atom, alkylcarbonyl group having 2 to 10 carbon atoms, arylcarbonyl group having 7 to 20 carbon atoms, aralkyl group having 7 to 20 carbon atoms, alkoxyalkyl group having 2 to 10 carbon atoms, trialkylsilyl group having 3 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, alternatively, R1 and R2 may be connected to form a >C=O group together with a carbon atom to which they are connected, R3 and R4 may be connected to form a >C=O group together with a carbon atom to which they are connected, R5 and R6 may be connected to form a >C=O group together with a carbon atom to which they are connected, any two of R1, R2, R3, R4, R5 and R6 may be connected to form an optionally substituted polymethylene group having 1 to 4 carbon atoms, one or no-mutually-adjacent two methylene groups constituting the polymethylene group may be substituted by an oxygen atom, one or two ethylene groups constituting the polymethylene group may be substituted by a vinylene group, no-mutually-adjacent two methylene groups constituting the polymethylene group may be mutually connected via an oxygen atom, methylene group, ethylene group or vinylene group.].

  下式(1)的 N-叔丁氧羰基-2-吡咯烷酮： [其中，R1、R2、R3、R4、R5 和 R6 各自独立地代表氢原子、卤素原子、氰基、任选取代的具有 1 至 10 个碳原子的直链、支链或环状烷基、任选取代的具有 2 至 10 个碳原子的直链、支链或环状烯基、任选取代的具有 6 至 20 个碳原子的芳基、任选取代的氨基、-Ra和 Rb 各自独立地代表氢原子、具有 2 至 10 个碳原子的烷基羰基、具有 7 至 20 个碳原子的芳基羰基、具有 7 至 20 个碳原子的芳烷基、具有 2 至 10 个碳原子的烷氧基烷基、具有 3 至 10 个碳原子的三烷基硅基、具有 1 至 10 个碳原子的烷基、具有 6 至 20 个碳原子的芳基、 或者，R1 和 R2 连接在一起，形成一个 >C=O 基团，R3 和 R4 连接在一起，形成一个 >C=O 基团，R5 和 R6 连接在一起，形成一个 >C=O 基团，R7 和 R8 连接在一起，形成一个 >C=O 基团，R8 和 R9 连接在一起，形成一个 >C=O 基团，R1 和 R2 连接在一起，形成一个 >C=O 基团，R3 和 R4 连接在一起，形成一个 >C=O 基团，R5 和 R6 连接在一起，形成一个 >C=O 基团、 R1、R2、R3、R4、R5 和 R6 中的任意两个可连接成具有 1 至 4 个碳原子的任选取代的聚亚甲基，构成聚亚甲基的一个或不相邻的两个亚甲基可被一个氧原子取代、构成聚亚甲基的一个或两个亚乙基基团可被亚乙烯基团取代，构成聚亚甲基的不相邻的两个亚甲基基团可通过氧原子、亚甲基基团、亚乙基基团或亚乙烯基团相互连接。].