(+/-)-3-(1-oxo-4-phenylbutan-2-yloxy)propanoic acid | 1242309-89-2

• 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: (+/-)-3-(1-oxo-4-phenylbutan-2-yloxy)propanoic acid
• 英文别名: 3-(1-Oxo-4-phenylbutan-2-yl)oxypropanoic acid
• CAS: 1242309-89-2
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: WOXHOJFCXBRQHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-3-(1-oxo-4-phenylbutan-2-yloxy)propanoic acid 在 2-bromo-N-propylpyridinium triflate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (1S,4R,5S)-4-(2-phenylethyl)-3,6-dioxabicyclo[3.2.0]heptan-7-one 、 (1R,4R,5R)-4-(2-phenylethyl)-3,6-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：

  (+/-)-3-(5-phenylpent-1-en-3-yloxy)propanoic acid 在 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到(+/-)-3-(1-oxo-4-phenylbutan-2-yloxy)propanoic 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