4-(5-甲氧基嘧啶-4-基)哌嗪-1-羧酸乙酯 | 1027025-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 4-(5-甲氧基嘧啶-4-基)哌嗪-1-羧酸乙酯
• 英文名称: Ethyl 4-(5-methoxypyrimidin-4-yl)piperazine-1-carboxylate
• CAS: 1027025-80-4
• 化学式: C₁₂H₁₈N₄O₃
• 分子量: 266.3
• InChiKey: QXMUZXLLQSHWQA-UHFFFAOYSA-N

物化性质

• 沸点：
  425.1±45.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(5-甲氧基嘧啶-4-基)哌嗪-1-羧酸乙酯 生成 5-甲氧基-4-(哌嗪-1-基)嘧啶
  参考文献：
  名称：

  J. Org. Chem. 1997, 62, 9192-9202

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基-5-甲氧基嘧啶 在 三乙胺 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 4-(5-甲氧基嘧啶-4-基)哌嗪-1-羧酸乙酯
  参考文献：
  名称：

  An Efficient Fischer Indole Synthesis of Avitriptan, a Potent 5-HT_1D Receptor Agonist

  摘要：

  An efficient synthesis of the antimigraine drug candidate avitriptan (1, BMS 180048) is reported. The key step is a two-phase Fischer indolization reaction between hydrazine 6 and 5-chlorovaleraldehyde, 20, to give the chloropropylindole 35, which is susceptible to acid-catalyzed degradation under the reaction conditions required for its formation. Sequential coupling of 35 with piperazine, 26, and 4-chloro-5-methoxypyrimidine, 24, gives the title compound in 40-45% overall yield. Significant improvements in the syntheses of the known starting materials, hydrazine 6, 5-chlorovaleraldehyde, 20, and 4-chloro-5-methoxypyrimidine, 24, were also achieved.

  DOI：

  10.1021/jo971368q

文献信息

• An Efficient Fischer Indole Synthesis of Avitriptan, a Potent 5-HT_1D Receptor Agonist
  作者：Paul R. Brodfuehrer、Bang-Chi Chen、Thomas R. Sattelberg、Patrick R. Smith、Jayachandra P. Reddy、Derron R. Stark、Sandra L. Quinlan、J. Gregory Reid、John K. Thottathil、Shaopeng Wang

  DOI：10.1021/jo971368q

  日期：1997.12.1

  An efficient synthesis of the antimigraine drug candidate avitriptan (1, BMS 180048) is reported. The key step is a two-phase Fischer indolization reaction between hydrazine 6 and 5-chlorovaleraldehyde, 20, to give the chloropropylindole 35, which is susceptible to acid-catalyzed degradation under the reaction conditions required for its formation. Sequential coupling of 35 with piperazine, 26, and 4-chloro-5-methoxypyrimidine, 24, gives the title compound in 40-45% overall yield. Significant improvements in the syntheses of the known starting materials, hydrazine 6, 5-chlorovaleraldehyde, 20, and 4-chloro-5-methoxypyrimidine, 24, were also achieved.
• J. Org. Chem. 1997, 62, 9192-9202
  作者：

  DOI：——

  日期：——