(1S,3R,6R)-3-phenethyl-2,7-dioxabicyclo[4.2.0]octan-8-one | 1242310-03-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,3R,6R)-3-phenethyl-2,7-dioxabicyclo[4.2.0]octan-8-one
• CAS: 1242310-03-7
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: TVTRGHYRBWFLPS-UPJWGTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (R)-2-(6-oxo-1-phenylhexan-3-yloxy)acetic acid 在 2-bromo-N-propylpyridinium triflate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以26%的产率得到(1S,3R,6R)-3-phenethyl-2,7-dioxabicyclo[4.2.0]octan-8-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