(S)-1,1-bis(4-fluorophenyl)-1-hydroxy-3,3-dimethylbutan-2-aminium trifluoroacetate | 1284303-90-7

• 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: (S)-1,1-bis(4-fluorophenyl)-1-hydroxy-3,3-dimethylbutan-2-aminium trifluoroacetate
• 英文别名: (2S)-2-amino-1,1-bis(4-fluorophenyl)-3,3-dimethylbutan-1-ol;2,2,2-trifluoroacetic acid
• CAS: 1284303-90-7
• 化学式: C₂HF₃O₂*C₁₈H₂₁F₂NO
• 分子量: 419.392
• InChiKey: WBXGWWRHGPFRPU-NTISSMGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  L-叔亮氨酸甲酯盐酸盐 、 4-氟苯基溴化镁 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.58h， 生成 (S)-1,1-bis(4-fluorophenyl)-1-hydroxy-3,3-dimethylbutan-2-aminium trifluoroacetate
  参考文献：
  名称：

  Enantioselective Diels–Alder Reaction of 1,2-Dihydropyridines with Aldehydes Using β-Amino Alcohol Organocatalyst

  摘要：

  The enantioselective Diels Alder reaction of 1,2-dihydropyridines with aldehydes using an easily prepared optically active beta-amino alcohol catalyst was found to provide optically active isoquinuclidines, an efficient synthetic intermediate of pharmaceutically important compounds such as oseltamivir phosphate, with a satisfactory chemical yield and enantioselectivity (up to 96%, up to 98% ee). In addition, the obtained highly optically pure isoquinuclidine was easily converted to an optically active piperidine having four successive carbon centers.

  DOI：

  10.1021/jo501433c

文献信息

• A highly enantioselective Diels–Alder reaction of 1,2-dihydropyridine using a simple β-amino alcohol organocatalyst for a practical synthetic methodology of oseltamivir intermediate
  作者：Chonticha Suttibut、Yoshihito Kohari、Ko Igarashi、Hiroto Nakano、Masafumi Hirama、Chigusa Seki、Haruo Matsuyama、Koji Uwai、Nobuhiro Takano、Yuko Okuyama、Kenichi Osone、Mitsuhiro Takeshita、Eunsang Kwon

  DOI：10.1016/j.tetlet.2011.06.109

  日期：2011.9

  An easily prepared chiral amino alcohol catalyst was found to provide an efficient synthetic intermediate of oseltamivir with excellent chemical yield and enantioselectivity (up to 98% yield and up to 98% ee) in enantioselective Diels-Alder reactions of 1,2-dihydropylidines with acroleins. (C) 2011 Elsevier Ltd. All rights reserved.