tert-Butyl (+/-)-4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidin-2-one-1-carboxylate | 360042-78-0

• 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: tert-Butyl (+/-)-4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidin-2-one-1-carboxylate
• 英文别名: 1-(tert-butoxycarbonyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one；Tert-butyl 4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxopyrrolidine-1-carboxylate
• CAS: 360042-78-0
• 化学式: C₂₁H₂₉NO₅
• 分子量: 375.465
• InChiKey: FBLIRTIXRAHTLL-UHFFFAOYSA-N

物化性质

• 熔点：
  81-83 °C
• 沸点：
  523.4±50.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-Butyl (+/-)-4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidin-2-one-1-carboxylate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以100%的产率得到咯利普兰
  参考文献：
  名称：

  Synthesis of 4-Aryl-2-pyrrolidones and β-Aryl-γ-amino-butyric Acid (GABA) Analogues by Heck Arylation of 3-Pyrrolines with Arenediazonium Tetrafluoroborates. Synthesis of (±)-Rolipram on a Multigram Scale and Chromatographic Resolution by Semipreparative Chiral Simulated Moving Bed Chromatography

  摘要：

  We report herein a new, practical, and economic synthesis of the phosphodiesterase inhibitor Rolipram on a multigram. scale as well as the synthesis of new 4-aryl pyrrolidones and beta-aryl-gamma-amino butyric acids (GABA derivatives) employing an efficient Heck-Matsuda arylation of 3-pyrroline with aryldiazonium tetrafluoroborates. Racemic Rolipram was resolved into its enantiomers using chiral simulated moving bed chromatography having the low-cost microcrystalline cellulose triacetate as a chiral stationary phase.

  DOI：

  10.1021/jo0484880
• 作为产物：
  描述：

  N-Boc-3-吡咯啉 在 palladium diacetate 、 四丙基高钌酸铵 、 水 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.75h， 生成 tert-Butyl (+/-)-4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidin-2-one-1-carboxylate
  参考文献：
  名称：

  Synthesis of 4-Aryl-2-pyrrolidones and β-Aryl-γ-amino-butyric Acid (GABA) Analogues by Heck Arylation of 3-Pyrrolines with Arenediazonium Tetrafluoroborates. Synthesis of (±)-Rolipram on a Multigram Scale and Chromatographic Resolution by Semipreparative Chiral Simulated Moving Bed Chromatography

  摘要：

  We report herein a new, practical, and economic synthesis of the phosphodiesterase inhibitor Rolipram on a multigram. scale as well as the synthesis of new 4-aryl pyrrolidones and beta-aryl-gamma-amino butyric acids (GABA derivatives) employing an efficient Heck-Matsuda arylation of 3-pyrroline with aryldiazonium tetrafluoroborates. Racemic Rolipram was resolved into its enantiomers using chiral simulated moving bed chromatography having the low-cost microcrystalline cellulose triacetate as a chiral stationary phase.

  DOI：

  10.1021/jo0484880

文献信息

• First Highly Regio- and Diastereoselective [3+2] Cycloaddition of Chiral Nonracemic Fischer Carbene Complexes with Azomethine Ylides: An Enantioselective Synthesis of (+)-Rolipram
  作者：José Barluenga、Manuel A. Fernández-Rodríguez、Enrique Aguilar、Félix Fernández-Marí、Alejandro Salinas、Bernardo Olano

  DOI：10.1002/1521-3765(20010817)7:16<3533::aid-chem3533>3.0.co;2-e

  日期：2001.8.17

  A new procedure for the synthesis of 1,3,4-trisubstituted and 1,4-disubstituted pyrrolidin-2-one derivatives in an enantioselective fashion is reported. The 1,3-dipolar cycloaddition of (+/-)-menthol and (-)-8-phenylmenthol derived Fischer alkoxy alkenyl carbene complexes with in situ generated functionalized azomethine ylides gives the corresponding cycloadducts as chelated tetracarbonyl Fischer carbene

  报道了以对映选择性的方式合成1,3,4-三取代和1,4-二取代的吡咯烷-2-酮衍生物的新方法。（+/-）-薄荷醇和（-）-8-苯基薄荷醇的1，3-偶极环加成与原位产生的官能化的偶氮甲亚胺的费希尔烷氧基烯基卡宾卡宾配合物产生相应的环加合物，为螯合的四羰基菲舍尔卡宾配合物。在所有情况下仅检测到一种区域异构体，并且当使用（-）-8-苯基薄荷醇衍生的卡宾时，反应的非对映选择性非常高。环加合物的氧化和进一步转化提供了容易获得吡咯烷基-2-酮的途径。利用这种新开发的方法，可以很容易地通过四个步骤以20％的总产率制备抗炎和抗抑郁药（+）-咯利普兰。