N-ethyl-5-(3-bromo-2,6-dimethoxybenzamido)-4-oxopentanamide | 125558-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-ethyl-5-(3-bromo-2,6-dimethoxybenzamido)-4-oxopentanamide
• 英文别名: 3-bromo-N-[5-(ethylamino)-2,5-dioxopentyl]-2,6-dimethoxybenzamide
• CAS: 125558-33-0
• 化学式: C₁₆H₂₁BrN₂O₅
• 分子量: 401.257
• InChiKey: VKXYKKZTFZNFRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  93.73
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-ethyl-5-(3-bromo-2,6-dimethoxybenzamido)-4-oxopentanamide 在 氨 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以100%的产率得到3-溴-N-[(1-乙基-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
• 作为产物：
  描述：

  3-溴-2,6-二甲氧基苯甲酰氯 在 N-甲基吗啉 、 硫酸 、 三乙胺 、 lithium diisopropyl amide 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.75h， 生成 N-ethyl-5-(3-bromo-2,6-dimethoxybenzamido)-4-oxopentanamide
  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：——