(S)-1-hydroxy-1,1,3-triphenylpropan-2-aminium trifluoroacetate | 1284303-86-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (S)-1-hydroxy-1,1,3-triphenylpropan-2-aminium trifluoroacetate
• 英文别名: (2S)-2-amino-1,1,3-triphenylpropan-1-ol;2,2,2-trifluoroacetic acid
• CAS: 1284303-86-1
• 化学式: C₂HF₃O₂*C₂₁H₂₁NO
• 分子量: 417.428
• InChiKey: PHGXSLBKIZVLAG-BDQAORGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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-1,1,3-三苯基-1-丙醇 、 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-1,1,3-triphenylpropan-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
• 作为试剂：
  描述：

  1-(phenoxycarbonyl)-1,2-dihydropyridine 在 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 (S)-1-hydroxy-1,1,3-triphenylpropan-2-aminium trifluoroacetate 、 sodium perchlorate 作用下， 以 水 、 乙腈 、 叔丁醇 为溶剂， 反应 25.5h， 生成
  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.
• Enantioselective Diels–Alder Reaction of 1,2-Dihydropyridines with Aldehydes Using β-Amino Alcohol Organocatalyst
  作者：Yoshihito Kohari、Yuko Okuyama、Eunsang Kwon、Taniyuki Furuyama、Nagao Kobayashi、Teppei Otuki、Jun Kumagai、Chigusa Seki、Koji Uwai、Gang Dai、Tatsuo Iwasa、Hiroto Nakano

  DOI：10.1021/jo501433c

  日期：2014.10.17

  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.