1-(4-fluorophenyl)-4-isopropyl-5-styryl-1H-pyrazole-3-carboxylic acid ethyl ester | 1260620-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-fluorophenyl)-4-isopropyl-5-styryl-1H-pyrazole-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 1-(4-fluorophenyl)-5-(2-phenylethenyl)-4-propan-2-ylpyrazole-3-carboxylate；ethyl 1-(4-fluorophenyl)-5-(2-phenylethenyl)-4-propan-2-ylpyrazole-3-carboxylate
• CAS: 1260620-81-2
• 化学式: C₂₃H₂₃FN₂O₂
• 分子量: 378.446
• InChiKey: WASVJNRHVFMNDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)-4-isopropyl-5-styryl-1H-pyrazole-3-carboxylic acid ethyl ester 在 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 1-(4-fluorophenyl)-5-formyl-4-isopropyl-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  Development of an Early Enabling Synthesis for PF-03052334-02: A Novel Hepatoselective HMG-CoA Reductase Inhibitor

  摘要：

  Early process development work toward a promising pyrazole-based HMG-CoA reductase inhibitor is described. PF-03052334-02 (1) was prepared in 14 synthetic steps with a 21% overall yield, highlighted by a modified three-step hydroxypyrazole formation in which the yield was improved from 37% to 73%, a Suzuki/ozonolysis pathway that streamlined the downstream chemistry, and a reversed Wittig olefination strategy that improved the key coupling step from 50% to 95% yield. Multiple process hazards and most chromatography steps were removed, and a highly effective active pharmaceutical ingredient (API) salt formation, purification, and isolation protocol was also developed.

  DOI：

  10.1021/op100268e