(2R,3S)-3-(tert-butyldimethylsilyloxymethyl)-1-methyl-2-phenylazirane | 363620-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2R,3S)-3-(tert-butyldimethylsilyloxymethyl)-1-methyl-2-phenylazirane
• 英文别名: tert-butyl-dimethyl-[[(2S,3R)-1-methyl-3-phenylaziridin-2-yl]methoxy]silane
• CAS: 363620-52-4
• 化学式: C₁₆H₂₇NOSi
• 分子量: 277.482
• InChiKey: UQKBMCQQLIJWJR-BLBXNVQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  12.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-(tert-butyldimethylsilyloxymethyl)-1-methyl-2-phenylazirane 在 吡啶 、 potassium fluoride 、 氢氧化钾 、 sodium tetrahydroborate 、 sodium iodide 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 、 丙酮 为溶剂， 反应 26.0h， 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：

  (2R,3R)-3-(methylamino)-3-phenyl-1,2-propanediol 在 咪唑 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 (2R,3S)-3-(tert-butyldimethylsilyloxymethyl)-1-methyl-2-phenylazirane
  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

• 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.