3-溴-N-[(2-羟基-5-氧代吡咯烷-2-基)甲基]-2,6-二甲氧基苯甲酰胺 | 125558-31-8

• 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: 3-溴-N-[(2-羟基-5-氧代吡咯烷-2-基)甲基]-2,6-二甲氧基苯甲酰胺
• 中文别名: 2-亚氨基-3,4-二甲基-5-苯基噻唑烷茶叶碱-7-基乙酸酯
• 英文名称: 5-<(3-bromo-2,6-dimethoxybenzamido)methyl>-5-hydroxy-2-pyrrolidone
• 英文别名: 5-[(3-bromo-2,6-dimethoxybenzamido)methyl]-5-hydroxy-2-pyrrolidone；5-((3-Bromo-2,6-dimethoxybenzamido)methyl)-5-hydroxy-2-pyrrolidone；3-bromo-N-[(2-hydroxy-5-oxopyrrolidin-2-yl)methyl]-2,6-dimethoxybenzamide
• CAS: 125558-31-8
• 化学式: C₁₄H₁₇BrN₂O₅
• 分子量: 373.203
• InChiKey: QCIQHIFWWFPRHS-UHFFFAOYSA-N

物化性质

• 熔点：
  147-148 °C
• 沸点：
  571.4±50.0 °C(Predicted)
• 密度：
  1.513±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-溴-2,6-二甲氧基苯甲酰氯 在 盐酸 、 4-二甲氨基吡啶 、 氨 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 3-溴-N-[(2-羟基-5-氧代吡咯烷-2-基)甲基]-2,6-二甲氧基苯甲酰胺
  参考文献：
  名称：

  Synthesis of 5-Substituted 5-Hydroxy-2-pyrrolidones, Metabolites of the Antipsychotic Benzamide Remoxipride.

  摘要：

  This paper describes the synthesis of 5-[(3-bromo-2,6-dimethoxybenzamido)-methyl]-5-hydroxy-2-pyrrolidon e (3) and its 1-ethyl analogue 2, two urinary metabolites of the dopamine D-2 antagonist remoxipride [1, (S)-3-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2, 6-dimethoxybenzamide]. Two synthetic schemes leading to a common intermediate, 5-benzamido-4-oxopentanoic acid 4, were developed. This key intermediate permits conversion into either metabolite. Reaction of 4 with isobutyl chloroformate furnished a mixed carbonic anhydride, which upon treatment with ethylamine or ammonia gave the 4-oxopentanamides 5 and 6, respectively. Ring-closure afforded the corresponding 5-hydroxy-2-pyrrolidones 2 and 3.

  DOI：

  10.3891/acta.chem.scand.43-0476

文献信息

• GAWELL, LARS;HAGBERG, CURT-ERIC;HOGBERG, THOMAS;WIDMAN, MARIANNE, ACTA CHEM. SCAND., 43,(1989) N, C. 476-480
  作者：GAWELL, LARS、HAGBERG, CURT-ERIC、HOGBERG, THOMAS、WIDMAN, MARIANNE

  DOI：——

  日期：——
• Synthesis of 5-Substituted 5-Hydroxy-2-pyrrolidones, Metabolites of the Antipsychotic Benzamide Remoxipride.
  作者：Lars Gawell、Curt-Eric Hagberg、Thomas Högberg、Marianne Widman、Kjell Ankner、Ulf Junggren、Bo Lamm、Peter Nordberg、Magnus Erickson、Inger Grundevik、Inger Hagin、Kurt-Jürgen Hoffman、Svante Johansson、Sam Larsson、Ingalil Löfberg、Kristina Ohlson、Björn Persson、Inger Skånberg、Lija Tekenbergs-Hjelte

  DOI：10.3891/acta.chem.scand.43-0476

  日期：——

  This paper describes the synthesis of 5-[(3-bromo-2,6-dimethoxybenzamido)-methyl]-5-hydroxy-2-pyrrolidon e (3) and its 1-ethyl analogue 2, two urinary metabolites of the dopamine D-2 antagonist remoxipride [1, (S)-3-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2, 6-dimethoxybenzamide]. Two synthetic schemes leading to a common intermediate, 5-benzamido-4-oxopentanoic acid 4, were developed. This key intermediate permits conversion into either metabolite. Reaction of 4 with isobutyl chloroformate furnished a mixed carbonic anhydride, which upon treatment with ethylamine or ammonia gave the 4-oxopentanamides 5 and 6, respectively. Ring-closure afforded the corresponding 5-hydroxy-2-pyrrolidones 2 and 3.