Tert-butyl 4-(3,4-dimethoxyphenyl)-2-oxopyrrolidine-1-carboxylate | 432049-61-1

• 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-(3,4-dimethoxyphenyl)-2-oxopyrrolidine-1-carboxylate
• 英文别名: tert-butyl 4-(3,4-dimethoxyphenyl)-2-oxopyrrolidine-1-carboxylate
• CAS: 432049-61-1
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: WYEINTVAHPAXID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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-(3,4-dimethoxyphenyl)-2-oxopyrrolidine-1-carboxylate 在 盐酸 作用下， 以 水 为溶剂， 反应 18.0h， 以86%的产率得到4-Amino-3-(3,4-dimethoxy-phenyl)-butyric acid; hydrochloride
  参考文献：
  名称：

  Heck arylations of N -acyl-3-pyrroline and N -acyl-1,2,5,6-tetrahydropyridine with aryldiazonium salts. Short syntheses of aryl γ- and δ-lactams, baclofen, homobaclofen and analogues

  摘要：

  Heck arylation of N-acyl-3-pyrrolines and an N-acyl-tetrahydropyridine with aryldiazonium tetrafluoroborates under phosphine-free conditions proceeded smoothly to give alpha-hydroxycarbamates (hemiaminals) or alpha-alkoxycarbamates which were oxidized to the desired gamma- and delta-lactams. Acidic hydrolysis of the gamma-lactams produced a series of arylated GABA derivatives, including baclofen, a useful therapeutic drug. in only three steps with ail overall yield of 63 76%, Starting from N-acyl-tetrahydropyridine, aryl-delta-lactams and higher homologues of baclofen can be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02267-5
• 作为产物：
  描述：

  N-Boc-3-吡咯啉 在 palladium diacetate pyridinium chlorochromate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 Tert-butyl 4-(3,4-dimethoxyphenyl)-2-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  Heck arylations of N -acyl-3-pyrroline and N -acyl-1,2,5,6-tetrahydropyridine with aryldiazonium salts. Short syntheses of aryl γ- and δ-lactams, baclofen, homobaclofen and analogues

  摘要：

  Heck arylation of N-acyl-3-pyrrolines and an N-acyl-tetrahydropyridine with aryldiazonium tetrafluoroborates under phosphine-free conditions proceeded smoothly to give alpha-hydroxycarbamates (hemiaminals) or alpha-alkoxycarbamates which were oxidized to the desired gamma- and delta-lactams. Acidic hydrolysis of the gamma-lactams produced a series of arylated GABA derivatives, including baclofen, a useful therapeutic drug. in only three steps with ail overall yield of 63 76%, Starting from N-acyl-tetrahydropyridine, aryl-delta-lactams and higher homologues of baclofen can be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02267-5

文献信息

• Microwave-Assisted Heck Arylations of Non-Activated<i>N</i>-Acyl-3-pyrrolines with Arenediazonium Tetrafluoroborates
  作者：Fernanda G. Finelli、Marla N. Godoi、Carlos R. D. Correia

  DOI：10.5935/0103-5053.20150051

  日期：——

  Successful Heck-Matsuda arylations of non-activated olefins applying microwave irradiation as an alternative heating mode are presented. Cleaner reactions were performed with arenediazonium tetrafluoroborates bearing electron-donating and electron-withdrawing groups in good to excellent yields with reaction times reduced from 3.5-18 h to 12-30 min.
• Heck arylations of N -acyl-3-pyrroline and N -acyl-1,2,5,6-tetrahydropyridine with aryldiazonium salts. Short syntheses of aryl γ- and δ-lactams, baclofen, homobaclofen and analogues
  作者：Marcos José S. Carpes、Carlos Roque D. Correia

  DOI：10.1016/s0040-4039(01)02267-5

  日期：2002.1

  Heck arylation of N-acyl-3-pyrrolines and an N-acyl-tetrahydropyridine with aryldiazonium tetrafluoroborates under phosphine-free conditions proceeded smoothly to give alpha-hydroxycarbamates (hemiaminals) or alpha-alkoxycarbamates which were oxidized to the desired gamma- and delta-lactams. Acidic hydrolysis of the gamma-lactams produced a series of arylated GABA derivatives, including baclofen, a useful therapeutic drug. in only three steps with ail overall yield of 63 76%, Starting from N-acyl-tetrahydropyridine, aryl-delta-lactams and higher homologues of baclofen can be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.