(R)-3-(tert-butyldimethylsilyloxy)-7-methyloct-6-enoic acid | 1242310-12-8

• 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)-3-(tert-butyldimethylsilyloxy)-7-methyloct-6-enoic acid
• CAS: 1242310-12-8
• 化学式: C₁₅H₃₀O₃Si
• 分子量: 286.487
• InChiKey: GTQISCJGGPHZAX-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-3-(tert-butyldimethylsilyloxy)-7-methyloct-6-enoic acid 在 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到(R)-3-(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
• 作为产物：
  描述：

  (R)-methyl 3-(tert-butyldimethylsilyloxy)-7-methyloct-6-enoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.33h， 以59%的产率得到(R)-3-(tert-butyldimethylsilyloxy)-7-methyloct-6-enoic 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