(1R,2R)-3-(tert-butyldimethylsilyloxy)-1-methylamino-1-phenylpropan-2-ol | 363620-51-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,2R)-3-(tert-butyldimethylsilyloxy)-1-methylamino-1-phenylpropan-2-ol
• 英文别名: (1R,2R)-3-[tert-butyl(dimethyl)silyl]oxy-1-(methylamino)-1-phenylpropan-2-ol
• CAS: 363620-51-3
• 化学式: C₁₆H₂₉NO₂Si
• 分子量: 295.497
• InChiKey: BVRLOTYDIDLSMK-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R)-3-(tert-butyldimethylsilyloxy)-1-methylamino-1-phenylpropan-2-ol 在 吡啶 、 potassium fluoride 、 氢氧化钾 、 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 sodium iodide 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二甲基亚砜 、 丙酮 为溶剂， 反应 50.0h， 生成 左旋伪麻黄碱
  参考文献：
  名称：

  Asymmetric synthesis of (−)-pseudoephedrine from (2S,3S)-3-phenyloxiran-2-ylmethanol. Stereospecific interchange of amino and alcohol functions

  摘要：

  A ring-opening reaction of N-methylaziridines with Boc(2)O/NaI has been applied to the asymmetric synthesis of pseudoephedrine. 3-Methylamino-3-phenyl-1,2-propanediol 1, derived from (2S,3S)-3-phenyloxiran-2-ylmethanol, was converted into the oxazolidin-2-one 4, a precursor of pseudoephedrine. The reaction occurs with a stereospecific interchange of amino and alcohol functions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00228-2
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 (2R,3R)-3-(methylamino)-3-phenyl-1,2-propanediol 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以81%的产率得到(1R,2R)-3-(tert-butyldimethylsilyloxy)-1-methylamino-1-phenylpropan-2-ol
  参考文献：
  名称：

  Asymmetric synthesis of (−)-pseudoephedrine from (2S,3S)-3-phenyloxiran-2-ylmethanol. Stereospecific interchange of amino and alcohol functions

  摘要：

  A ring-opening reaction of N-methylaziridines with Boc(2)O/NaI has been applied to the asymmetric synthesis of pseudoephedrine. 3-Methylamino-3-phenyl-1,2-propanediol 1, derived from (2S,3S)-3-phenyloxiran-2-ylmethanol, was converted into the oxazolidin-2-one 4, a precursor of pseudoephedrine. The reaction occurs with a stereospecific interchange of amino and alcohol functions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00228-2

文献信息

• Experimental and theoretical DFT study of the reaction of 3-amino-1,2-diols with dichloromethane and paraformaldehyde
  作者：A. Hamdach、E.M. El Hadrami、C. Hajji、E. Zaballos-García、J. Sepulveda-Arques、R.J. Zaragozá

  DOI：10.1016/j.tet.2004.07.090

  日期：2004.11

  The reactions of 3-phenyl-3-methylamino-1,2-propanediol 1a and 3-[(tert-butyldimethylsilyl)oxy]-1-methylamino-1-phenyl-2-propanol 1b with (CH2O)n and CH2Cl2 are appropriate procedures for the preparation of 1,3-oxazines or 1,3-oxazolidines under proper selection of kinetic or thermodynamic reaction conditions. The reaction of 1b with (CH2O)n or CH2Cl2, affords the oxazolidine 2b under kinetic conditions and then this compound can be slowly converted into 5-[(tert-butyldimethylsilyl)oxy]-3-methyl-4-phenyl-3,4,5,6-tetrahydro-2H-1,3-oxazine 3b under thermodynamic control. The mechanism proposed for this transformation and the effect of polar solvents on the acceleration of the reaction has been studied theoretically (DFT level). (C) 2004 Published by Elsevier Ltd.
• Asymmetric synthesis of (−)-pseudoephedrine from (2S,3S)-3-phenyloxiran-2-ylmethanol. Stereospecific interchange of amino and alcohol functions
  作者：Ma̱ Luisa Testa、Chakib Hajji、Elena Zaballos-Garcı́a、Ana Belén Garcı́a-Segovia、José Sepúlveda-Arques

  DOI：10.1016/s0957-4166(01)00228-2

  日期：2001.6

  A ring-opening reaction of N-methylaziridines with Boc(2)O/NaI has been applied to the asymmetric synthesis of pseudoephedrine. 3-Methylamino-3-phenyl-1,2-propanediol 1, derived from (2S,3S)-3-phenyloxiran-2-ylmethanol, was converted into the oxazolidin-2-one 4, a precursor of pseudoephedrine. The reaction occurs with a stereospecific interchange of amino and alcohol functions. (C) 2001 Elsevier Science Ltd. All rights reserved.