(1R,2R)-1-azido-3-methoxy-1-phenylpropan-2-ol | 250605-19-7

• 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: (1R,2R)-1-azido-3-methoxy-1-phenylpropan-2-ol
• CAS: 250605-19-7
• 化学式: C₁₀H₁₃N₃O₂
• 分子量: 207.232
• InChiKey: OUUYJVKHISTWIT-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-azido-3-methoxy-1-phenylpropan-2-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 36.0h， 以4.9 g的产率得到(1R,2R)-1-amino-3-methoxy-1-phenyl-2-propanol
  参考文献：
  名称：

  A New Family of Modular Chiral Ligands for the Catalytic Enantioselective Reduction of Prochiral Ketones

  摘要：

  A family of enantiomerically pure (4R,5R)-2-alkyl-4-phenyl-5-(R-oxymethyl) 1,3,2-oxazaborolidines (5) [boron substituent: H, CH3, n-C4H9; R-oxy group: CH3O, CH3OCH2CH2O, CH3(OCH2CH2)(2)O, PhCH2O, Ph2CHO, Ph3CO] has been prepared from (2S,3S)-2,3-epoxy-3-phenylpropanol (2) through a four-step sequence involving protection of the alcohol, regioselective ring-opening of the epoxide with sodium azide in acetonitrile in the presence of LiClO4, reduction of the azido group (H-2/PdC/MeOH or NaBH4/THF-MeOH), and formation of the oxazaborolidine ring with the appropriate boron reagent. Both the boron substituent and the R-oxy group have been optimized for maximal enantioselectivity in the reduction of prochiral ketones with borane. The optimal oxazaborolidine (5a-Me) [boron substituent: CH3; R-oxy group: CH3O] has been employed (10% molar amount, THF, 0 degrees C to room temperature) in the reduction of a representative family of 10 substrates comprising alkyl aryl ketones and dialkyl ketones. In these reductions, Ba-Rie induces the formation of secondary alcohols of S configuration with high enantioselectivity (93% mean enantiomeric excess). The origin of the enantioselectivity in the reduction has been rationalized by means of semiempirical AM1 calculations.

  DOI：

  10.1021/jo990942q
• 作为产物：
  描述：

  (2S,3S)-2-(甲氧基甲基)-3-苯基环氧乙烷 在 sodium azide 、 lithium perchlorate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以6.17 g的产率得到(1R,2R)-1-azido-3-methoxy-1-phenylpropan-2-ol
  参考文献：
  名称：

  A New Family of Modular Chiral Ligands for the Catalytic Enantioselective Reduction of Prochiral Ketones

  摘要：

  A family of enantiomerically pure (4R,5R)-2-alkyl-4-phenyl-5-(R-oxymethyl) 1,3,2-oxazaborolidines (5) [boron substituent: H, CH3, n-C4H9; R-oxy group: CH3O, CH3OCH2CH2O, CH3(OCH2CH2)(2)O, PhCH2O, Ph2CHO, Ph3CO] has been prepared from (2S,3S)-2,3-epoxy-3-phenylpropanol (2) through a four-step sequence involving protection of the alcohol, regioselective ring-opening of the epoxide with sodium azide in acetonitrile in the presence of LiClO4, reduction of the azido group (H-2/PdC/MeOH or NaBH4/THF-MeOH), and formation of the oxazaborolidine ring with the appropriate boron reagent. Both the boron substituent and the R-oxy group have been optimized for maximal enantioselectivity in the reduction of prochiral ketones with borane. The optimal oxazaborolidine (5a-Me) [boron substituent: CH3; R-oxy group: CH3O] has been employed (10% molar amount, THF, 0 degrees C to room temperature) in the reduction of a representative family of 10 substrates comprising alkyl aryl ketones and dialkyl ketones. In these reductions, Ba-Rie induces the formation of secondary alcohols of S configuration with high enantioselectivity (93% mean enantiomeric excess). The origin of the enantioselectivity in the reduction has been rationalized by means of semiempirical AM1 calculations.

  DOI：

  10.1021/jo990942q

文献信息

• A New Family of Modular Chiral Ligands for the Catalytic Enantioselective Reduction of Prochiral Ketones
  作者：Cristina Puigjaner、Anton Vidal-Ferran、Albert Moyano、Miquel A. Pericàs、Antoni Riera

  DOI：10.1021/jo990942q

  日期：1999.10.1

  A family of enantiomerically pure (4R,5R)-2-alkyl-4-phenyl-5-(R-oxymethyl) 1,3,2-oxazaborolidines (5) [boron substituent: H, CH3, n-C4H9; R-oxy group: CH3O, CH3OCH2CH2O, CH3(OCH2CH2)(2)O, PhCH2O, Ph2CHO, Ph3CO] has been prepared from (2S,3S)-2,3-epoxy-3-phenylpropanol (2) through a four-step sequence involving protection of the alcohol, regioselective ring-opening of the epoxide with sodium azide in acetonitrile in the presence of LiClO4, reduction of the azido group (H-2/PdC/MeOH or NaBH4/THF-MeOH), and formation of the oxazaborolidine ring with the appropriate boron reagent. Both the boron substituent and the R-oxy group have been optimized for maximal enantioselectivity in the reduction of prochiral ketones with borane. The optimal oxazaborolidine (5a-Me) [boron substituent: CH3; R-oxy group: CH3O] has been employed (10% molar amount, THF, 0 degrees C to room temperature) in the reduction of a representative family of 10 substrates comprising alkyl aryl ketones and dialkyl ketones. In these reductions, Ba-Rie induces the formation of secondary alcohols of S configuration with high enantioselectivity (93% mean enantiomeric excess). The origin of the enantioselectivity in the reduction has been rationalized by means of semiempirical AM1 calculations.