(S,E)-1-((tert-butyldimethylsilyl)oxy)-5-chloropent-4-en-2-yl 5-methylenedecanoate | 1449393-80-9

• 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,E)-1-((tert-butyldimethylsilyl)oxy)-5-chloropent-4-en-2-yl 5-methylenedecanoate
• 英文别名: [(E,2S)-1-[tert-butyl(dimethyl)silyl]oxy-5-chloropent-4-en-2-yl] 5-methylidenedecanoate
• CAS: 1449393-80-9
• 化学式: C₂₂H₄₁ClO₃Si
• 分子量: 417.104
• InChiKey: YFIHLJPAASGJRH-KZFLWGQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.37
• 重原子数：
  27
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,E)-1-((tert-butyldimethylsilyl)oxy)-5-chloropent-4-en-2-yl 5-methylenedecanoate 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以72%的产率得到(S,E)-5-chloro-1-hydroxypent-4-en-2-yl 5-methylenedecanoate
  参考文献：
  名称：

  Modular Strategies for Structure and Function Employed by Marine Cyanobacteria: Characterization and Synthesis of Pitinoic Acids

  摘要：

  Novel bioactive lipids were identified from a Guamanian cyanobacterium, the Pseudomonas aeruginosa quorum sensing inhibitor pitinoic acid A (1) and the anti-inflammatory pitinoic acids B (2) and C. The structure of 2 was confirmed by synthesis, which also allowed for biological evaluation. Since 2 is an ester of pitinoic acids A and C, it represents a prodrug strategy to liberate dual biological activity for the management of P. aeruginosa infections and their associated inflammation.

  DOI：

  10.1021/ol401396u
• 作为产物：
  描述：

  (S)-4-(3-chloroallyl)-2,2-dimethyl-1,3-dioxolane 在 咪唑 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.17h， 生成 (S,E)-1-((tert-butyldimethylsilyl)oxy)-5-chloropent-4-en-2-yl 5-methylenedecanoate
  参考文献：
  名称：

  Modular Strategies for Structure and Function Employed by Marine Cyanobacteria: Characterization and Synthesis of Pitinoic Acids

  摘要：

  Novel bioactive lipids were identified from a Guamanian cyanobacterium, the Pseudomonas aeruginosa quorum sensing inhibitor pitinoic acid A (1) and the anti-inflammatory pitinoic acids B (2) and C. The structure of 2 was confirmed by synthesis, which also allowed for biological evaluation. Since 2 is an ester of pitinoic acids A and C, it represents a prodrug strategy to liberate dual biological activity for the management of P. aeruginosa infections and their associated inflammation.

  DOI：

  10.1021/ol401396u