ethyl (3R)-3-phenoxybutanoate | 1403475-18-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl (3R)-3-phenoxybutanoate
• 英文别名: Ethyl (3S)-3-phenoxybutanoate；ethyl (3S)-3-phenoxybutanoate
• CAS: 1403475-18-2
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: CCVXQLMYBWRMLJ-JTQLQIEISA-N

物化性质

• 沸点：
  297.7±23.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-ethyl 3-phenoxybut-2-enoate 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 (R)-1-{(R_p)-2-[2-(dicyclohexylphosphino)phenyl]ferrocenyl}ethylbis[3,5-bis(trifluoromethyl)phenyl]phosphine 、 氢气 作用下， 以 氯苯 为溶剂， 80.0 ℃ 、896.34 kPa 条件下， 反应 20.0h， 以93%的产率得到ethyl (3R)-3-phenoxybutanoate
  参考文献：
  名称：

  Enantioselective Synthesis of β-Aryloxycarboxylic Esters via Asymmetric Hydrogenation of β-Aryloxy-α,β-Unsaturated Esters

  摘要：

  A novel synthesis of beta-aryloxycarboxylic esters via asymmetric hydrogenation of the corresponding beta-aryloxy-alpha,beta-unsaturated esters has been demonstrated. Bis(norbornadiene)rhodium(I) tetrafluoroborate (1 mol %) and Walphos W008-1 were used to generate the saturated products with high enantioselectivity and in high yield. The tolerability of the reaction to a diverse range of substituents on the aromatic ring was also explored.

  DOI：

  10.1021/ol302518y

文献信息

• Enantioselective Synthesis of β-Aryloxycarboxylic Esters via Asymmetric Hydrogenation of β-Aryloxy-α,β-Unsaturated Esters
  作者：Gavin W. Stewart、Michael Shevlin、Adam D. Gammack Yamagata、Andrew W. Gibson、Stephen P. Keen、Jeremy P. Scott

  DOI：10.1021/ol302518y

  日期：2012.11.2

  A novel synthesis of beta-aryloxycarboxylic esters via asymmetric hydrogenation of the corresponding beta-aryloxy-alpha,beta-unsaturated esters has been demonstrated. Bis(norbornadiene)rhodium(I) tetrafluoroborate (1 mol %) and Walphos W008-1 were used to generate the saturated products with high enantioselectivity and in high yield. The tolerability of the reaction to a diverse range of substituents on the aromatic ring was also explored.