(S)-1-azido-2-acetoxy-3-phenoxypropane | 140630-38-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-1-azido-2-acetoxy-3-phenoxypropane
• 英文别名: [(2S)-1-azido-3-phenoxypropan-2-yl] acetate
• CAS: 140630-38-2
• 化学式: C₁₁H₁₃N₃O₃
• 分子量: 235.243
• InChiKey: WYXIOJADRZHQFF-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  84.29
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-1-azido-2-acetoxy-3-phenoxypropane 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 生成 (2S)-(-)-1-氨基-3-苯氧基-2-丙醇
  参考文献：
  名称：

  Enzyme assisted preparation of enantiomerically pure β-adrenergic blockers II. Building blocks of high optical purity and their synthetic conversion

  摘要：

  Based on previous screening results a series of potential building blocks 2-4 for beta-adrenergic blockers were prepared both by enzymatic hydrolysis and acyltransfer and further transformed into the corresponding oxiranes and aminoalcohols of defined absolute configurations.

  DOI：

  10.1016/s0957-4166(00)80191-3
• 作为产物：
  描述：

  (1-azido-3-phenoxypropan-2-yl) acetate 生成 (S)-1-azido-2-acetoxy-3-phenoxypropane
  参考文献：
  名称：

  Enzyme assisted preparation of enantiomerically pure β-adrenergic blockers II. Building blocks of high optical purity and their synthetic conversion

  摘要：

  Based on previous screening results a series of potential building blocks 2-4 for beta-adrenergic blockers were prepared both by enzymatic hydrolysis and acyltransfer and further transformed into the corresponding oxiranes and aminoalcohols of defined absolute configurations.

  DOI：

  10.1016/s0957-4166(00)80191-3

文献信息

• Lipase-Catalyzed Kinetic Resolution of the Racemic Mixtures of 1-Aryloxy-3-Nitrato-and 1-Aryloxy-3-Azido-2-Propanols
  作者：Beata Pchelka、Justyna Radomska、Jan Plenkiewicz

  DOI：10.1080/00397919808004470

  日期：1998.12

  Abstract The racemic mixtures of 1-aryloxy-3-nitrato-2-propanols and 1-aryloxy-3-azido-2-propanols were resolved with moderate selectivity by the lipase-mediated acylation with vinyl acetate. The effects of the nature, position, and spatial requirements of the phenyl-ring substituents on the resolution degree were investigated.

  摘要 1-芳氧基-3-硝基-2-丙醇和1-芳氧基-3-叠氮基-2-丙醇的外消旋混合物通过脂肪酶介导的乙酸乙烯酯酰化以中等选择性拆分。研究了苯环取代基的性质、位置和空间要求对分辨率的影响。
• Dynamic Kinetic Resolution of β-Azido Alcohols. An Efficient Route to Chiral Aziridines and β-Amino Alcohols
  作者：Oscar Pàmies、Jan-E. Bäckvall

  DOI：10.1021/jo015579d

  日期：2001.6.1

  Enzymatic resolution of beta-azido alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution. A variety of racemic beta-azido alcohols were efficiently transformed to the corresponding enantiomerically pure acetates (ee up to 99% and conversion up to 98%). The synthetic utility of this procedure has been illustrated by the practical synthesis

  β-叠氮基醇的酶促拆分与钌催化的醇异构化相结合，成功实现了动态动力学拆分。各种外消旋β-叠氮基醇被有效地转化为相应的对映体纯的乙酸酯（ee最高可达99％，转化率最高可达98％）。实际合成（S）-丙醇I和（R）-β-叠氮基-α-（4-甲氧基苯基）乙醇（（R）-1c）（denopamine的直接前体）的实际合成说明了该方法的实用性二。