(S)-4-(tert-butyldimethylsilyloxy)-7-oxoheptanoic acid | 1242309-78-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-4-(tert-butyldimethylsilyloxy)-7-oxoheptanoic acid
• CAS: 1242309-78-9
• 化学式: C₁₃H₂₆O₄Si
• 分子量: 274.433
• InChiKey: LNASSYHZRGSTNI-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  (S)-4-(tert-butyldimethylsilyloxy)-7-oxoheptanoic acid 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， 反应 72.0h， 以10%的产率得到(1R,3S,6S)-3-(tert-butyldimethylsilyloxy)-7-oxabicyclo[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
• 作为产物：
  描述：

  (S)-4-(tert-butyldimethylsilyloxy)oct-7-enoic acid 在 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(S)-4-(tert-butyldimethylsilyloxy)-7-oxoheptanoic 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