(1S,2S)-2-(((1,3-dioxolan-2-yl)methyl)(methyl)amino)-1-phenylpropan-1-ol | 1203563-79-4

• 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: (1S,2S)-2-(((1,3-dioxolan-2-yl)methyl)(methyl)amino)-1-phenylpropan-1-ol
• 英文别名: (1S,2S)-2-[1,3-dioxolan-2-ylmethyl(methyl)amino]-1-phenylpropan-1-ol
• CAS: 1203563-79-4
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: WCAZASFEXQVQAU-SMDDNHRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴甲基-1,3-二氧戊烷 、 (1S,2S)-2-甲氨基-1-苯基丙-1-醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到(1S,2S)-2-(((1,3-dioxolan-2-yl)methyl)(methyl)amino)-1-phenylpropan-1-ol
  参考文献：
  名称：

  A structural examination of the impact of oxygenated side chains in Ephedra compounds in the catalytic asymmetric addition of diethylzinc to aldehydes

  摘要：

  An investigation of the impact of oxygenated side chains in Ephedra compounds on the catalytic asymmetric addition of diethylzinc to aldehydes has been conducted. (1R,2S)-Ephedrine and (1S,2S)-pseudoephedrine were alkylated with either alkyl halides or beta-alkoxyalkyl halides to afford a series of ligands 9a-h and 10a-h. These compounds were employed in the enantioselective addition of diethylzinc to a variety of aldehydes. It was determined that the presence of oxygen could have a negative effect in terms of obtaining high levels of enantiomeric discrimination, but the effect is diminished with higher levels of substitution near the oxygen. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.028
• 作为试剂：
  描述：

  diethylzinc 、 苯甲醛 在 (1S,2S)-2-(((1,3-dioxolan-2-yl)methyl)(methyl)amino)-1-phenylpropan-1-ol 作用下， 以 正己烷 、 甲苯 为溶剂， 生成 (R)-(+)-1-苯基-1-丙醇 、 S(-)-1-苯基-1-丙醇
  参考文献：
  名称：

  A structural examination of the impact of oxygenated side chains in Ephedra compounds in the catalytic asymmetric addition of diethylzinc to aldehydes

  摘要：

  An investigation of the impact of oxygenated side chains in Ephedra compounds on the catalytic asymmetric addition of diethylzinc to aldehydes has been conducted. (1R,2S)-Ephedrine and (1S,2S)-pseudoephedrine were alkylated with either alkyl halides or beta-alkoxyalkyl halides to afford a series of ligands 9a-h and 10a-h. These compounds were employed in the enantioselective addition of diethylzinc to a variety of aldehydes. It was determined that the presence of oxygen could have a negative effect in terms of obtaining high levels of enantiomeric discrimination, but the effect is diminished with higher levels of substitution near the oxygen. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.028