(R)-4-(tert-butyldimethylsilyloxy)-6-oxohexanoic acid | 1242309-59-6

• 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: (R)-4-(tert-butyldimethylsilyloxy)-6-oxohexanoic acid
• 英文别名: (4R)-4-[tert-butyl(dimethyl)silyl]oxy-6-oxohexanoic acid
• CAS: 1242309-59-6
• 化学式: C₁₂H₂₄O₄Si
• 分子量: 260.406
• InChiKey: LSGDTQXTOZJKKG-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (R)-4-(tert-butyldimethylsilyloxy)-6-oxohexanoic 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， 生成 (1S,3R,5R)-3-(tert-butyldimethylsilyloxy)-6-oxabicyclo[3.2.0]heptan-7-one 、 (1R,3R,5S)-3-(tert-butyldimethylsilyloxy)-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
• 作为产物：
  描述：

  (R)-4-tert-butyldimethylsiloxy-1-trimethylsiloxy-1-cyclohexene 在 2,6-二甲基吡啶 、 臭氧 、 solvent red 19 、 二甲基硫 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以65%的产率得到(R)-4-(tert-butyldimethylsilyloxy)-6-oxohexanoic 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