(3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-2-(4H-1,2,4-triazol-4-yl)butan-1-ol | 1474024-76-4

• 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: (3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-2-(4H-1,2,4-triazol-4-yl)butan-1-ol
• 英文别名: (3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-2-(1,2,4-triazol-4-yl)butan-1-ol
• CAS: 1474024-76-4
• 化学式: C₁₆H₁₄F₃N₅O
• 分子量: 349.315
• InChiKey: JNNOHDCZPCEHPU-VQVVDHBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (R)-4-(1-(2-(2,4-difluorophenyl)oxiran-2-yl)vinyl)-5-fluoropyrimidine 在 2,4,6-三异丙基苯磺酰基肼 、 碳酸氢钠 、 lithium chloride 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 23.0h， 生成 (3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-2-(4H-1,2,4-triazol-4-yl)butan-1-ol
  参考文献：
  名称：

  An Enantioselective Synthesis of Voriconazole

  摘要：

  A new seven-step sequence to access voriconazole, a clinically used antifungal agent, was developed. The initial catalytic asymmetric cyanosilylation is the key to constructing the consecutive tetra- and trisubstituted stereogenic centers. The fluoropyrimidine unit frequently triggered unexpected side reactions, but careful amendment of the reaction sequence allowed for the concise enantioselective synthesis.

  DOI：

  10.1021/jo4019528

文献信息

• An Enantioselective Synthesis of Voriconazole
  作者：Keiji Tamura、Makoto Furutachi、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.1021/jo4019528

  日期：2013.11.15

  A new seven-step sequence to access voriconazole, a clinically used antifungal agent, was developed. The initial catalytic asymmetric cyanosilylation is the key to constructing the consecutive tetra- and trisubstituted stereogenic centers. The fluoropyrimidine unit frequently triggered unexpected side reactions, but careful amendment of the reaction sequence allowed for the concise enantioselective synthesis.