(S)-1-hydroxy-3,3-dimethyl-1,1-diphenylbutan-2-amininium trifluoroacetate | 1284303-78-1

• 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-hydroxy-3,3-dimethyl-1,1-diphenylbutan-2-amininium trifluoroacetate
• 英文别名: (S)-1-hydroxy-3,3-dimethyl-1,1-diphenylbutan-2-amine trifluoroacetate；(2S)-2-amino-3,3-dimethyl-1,1-diphenylbutan-1-ol;2,2,2-trifluoroacetic acid
• CAS: 1284303-78-1
• 化学式: C₂HF₃O₂*C₁₈H₂₃NO
• 分子量: 383.411
• InChiKey: LUZSPQPROBZYTJ-NTISSMGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  27
• 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：
  7

反应信息

• 作为产物：
  描述：

  (S)-(-)-2-氨基-3,3-二甲基-1,1-二苯基-1-丁醇 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 0.08h， 以100%的产率得到(S)-1-hydroxy-3,3-dimethyl-1,1-diphenylbutan-2-amininium 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
• 作为试剂：
  描述：

  1-(phenoxycarbonyl)-1,2-dihydropyridine 、 丙烯醛 在 (S)-1-hydroxy-3,3-dimethyl-1,1-diphenylbutan-2-amininium trifluoroacetate 、 sodium tetrahydroborate 作用下， 以 水 、 乙腈 、 乙醇 为溶剂， 以98%的产率得到(1S,4S,7S)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2011.06.109