(+/-)-2-(5-oxo-1-phenylhexan-3-yloxy)ethanoic acid | 1242309-91-6

• 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: (+/-)-2-(5-oxo-1-phenylhexan-3-yloxy)ethanoic acid
• CAS: 1242309-91-6
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: SNUIOZWMAWJAHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+/-)-2-(5-oxo-1-phenylhexan-3-yloxy)ethanoic acid 在 2-bromo-N-propylpyridinium triflate 、 4-吡咯烷基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,3R,5R)-5-methyl-3-phenethyl-2,6-dioxabicyclo[3.2.0]heptan-7-one 、 (1R,3R,5S)-5-methyl-3-phenethyl-2,6-dioxabicyclo[3.2.0]heptan-7-one
  参考文献：
  名称：

  Double Diastereoselective, Nucleophile-Catalyzed Aldol Lactonizations (NCAL) Leading to β-Lactone Fused Carbocycles and Extensions to β-Lactone Fused Tetrahydrofurans

  摘要：

  A double diastereoselective variant of the nucleophile-catalyzed aldol lactonization (NCAL) process is described. This strategy delivers beta-lactone-fused carbocycles with good to excellent diastereoselectivities using cinchona alkaloid catalysts with enantioenriched aldehyde acids, which gave low diastereoselectivity based on substrate control alone. beta-Lactone-fused tetrahydrofurans are also prepared for the first time via the NCAL process; however, diastereoselectivity was only modestly improved when applying double diastereodifferentiation to these systems.

  DOI：

  10.1021/ol101388h
• 作为产物：
  描述：

  (+/-)-2-(5-methyl-1-phenylhex-5-en-3-yloxy)ethanoic acid 在 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到(+/-)-2-(5-oxo-1-phenylhexan-3-yloxy)ethanoic acid
  参考文献：
  名称：

  Double Diastereoselective, Nucleophile-Catalyzed Aldol Lactonizations (NCAL) Leading to β-Lactone Fused Carbocycles and Extensions to β-Lactone Fused Tetrahydrofurans

  摘要：

  A double diastereoselective variant of the nucleophile-catalyzed aldol lactonization (NCAL) process is described. This strategy delivers beta-lactone-fused carbocycles with good to excellent diastereoselectivities using cinchona alkaloid catalysts with enantioenriched aldehyde acids, which gave low diastereoselectivity based on substrate control alone. beta-Lactone-fused tetrahydrofurans are also prepared for the first time via the NCAL process; however, diastereoselectivity was only modestly improved when applying double diastereodifferentiation to these systems.

  DOI：

  10.1021/ol101388h