(1S,3R,4R,5R)-3-(tert-butyldimethylsilyloxy)-4-methyl-6-oxabicyclo[3.2.0]heptan-7-one | 1242309-83-6

• 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,4R,5R)-3-(tert-butyldimethylsilyloxy)-4-methyl-6-oxabicyclo[3.2.0]heptan-7-one
• 英文别名: (1S,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-4-methyl-6-oxabicyclo[3.2.0]heptan-7-one
• CAS: 1242309-83-6
• 化学式: C₁₃H₂₄O₃Si
• 分子量: 256.417
• InChiKey: LGISJNNWOJDGRE-UKKRHICBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  在 2-bromo-N-propylpyridinium triflate 、 O-TMS quinidine 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,3R,4R,5R)-3-(tert-butyldimethylsilyloxy)-4-methyl-6-oxabicyclo[3.2.0]heptan-7-one 、 (1R,3R,4R,5S)-3-(tertbutyldimethylsilyloxy)-4-methyl-6-oxabicyclo[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

文献信息

• Double Diastereoselective, Nucleophile-Catalyzed Aldol Lactonizations (NCAL) Leading to β-Lactone Fused Carbocycles and Extensions to β-Lactone Fused Tetrahydrofurans
  作者：Kay A. Morris、Kevin M. Arendt、Seong Ho Oh、Daniel Romo

  DOI：10.1021/ol101388h

  日期：2010.9.3

  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.