(2R,3R)-3-(methylamino)-3-phenyl-1,2-propanediol | 313640-98-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,3R)-3-(methylamino)-3-phenyl-1,2-propanediol
• 英文别名: (2R,3R)-3-(methylamino)-3-phenylpropane-1,2-diol
• CAS: 313640-98-1
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: LNHCVGWTRFGMJB-VHSXEESVSA-N

物化性质

• 沸点：
  346.2±42.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-(methylamino)-3-phenyl-1,2-propanediol 在 吡啶 、 咪唑 、 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 、 二氯甲烷 、 二甲基亚砜 、 丙酮 为溶剂， 反应 51.5h， 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：

  苯基甘油醇 、 甲胺 以 甲醇 、 水 为溶剂， 反应 14.0h， 以98%的产率得到(2R,3R)-3-(methylamino)-3-phenyl-1,2-propanediol
  参考文献：
  名称：

  Reaction of 3-Methylamino-1,2-diols with Dihalomethanes. Synthesis of Chiral 4-Substituted 3-Methyltetrahydro-1,3-oxazin-5-ols

  摘要：

  Enantiomerically pure 4,5-disubstituted 3-methyltetrahydro-1,3-oxazines have been obtained by reaction of 3-methylamino-1,2-diols with dichloromethane by regioselective differentiation of hydroxyl groups. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(00)00744-4

文献信息

• Synthesis of 1,3-Oxazolidines and 1,3-Dioxolanes by Reaction of (2<i>R</i>, 3<i>R</i>)-3-Methylamino-3-phenyl-1,2-propanediol with Electrophiles
  作者：Chakib Hajji、Elena Zaballos-García、José Sepúlveda-Arques

  DOI：10.1081/scc-120026865

  日期：2003.12.31

  The chemoselective reaction of (2R, 3R)-3-methylamino-3-phenyl-1,2-propanediol 1 with dimethoxypropane and dichloromethane under. different conditions are reported as useful preparative procedures, for the synthesis 1,3-oxazolidines and 1,3-dioxolanes.
• Reaction of 3-Methylamino-1,2-diols with Dihalomethanes. Synthesis of Chiral 4-Substituted 3-Methyltetrahydro-1,3-oxazin-5-ols
  作者：Chakib Hajji、Ma Luisa Testa、Roberto de la Salud-Bea、Elena Zaballos-Garcı́a、Juan Server-Carrió、José Sepúlveda-Arques

  DOI：10.1016/s0040-4020(00)00744-4

  日期：2000.10

  Enantiomerically pure 4,5-disubstituted 3-methyltetrahydro-1,3-oxazines have been obtained by reaction of 3-methylamino-1,2-diols with dichloromethane by regioselective differentiation of hydroxyl groups. (C) 2000 Published by Elsevier Science 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.