(2S,3E)-2,8-dihydroxyoct-3-enyl benzoate | 1226855-25-9

• 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: (2S,3E)-2,8-dihydroxyoct-3-enyl benzoate
• CAS: 1226855-25-9
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: HPZLNOBLVLSOCH-XYYIANASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3E)-2,8-dihydroxyoct-3-enyl benzoate 在 双(乙腈)氯化钯(II) 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以92%的产率得到(S,E)-2-(3-benzoyloxyprop-1-enyl)tetrahydro-2H-pyran
  参考文献：
  名称：

  A Short Access to Chiral Non-Racemic Oxa- and Azaheterocycles by Cross-Metathesis and Pd-Catalyzed Cyclization Sequence

  摘要：

  A concise synthesis of chiral non-racemic 2-(3-benzoyloxyprop-1-enyl)tetrahydrofuran (5a), tetrahydropyran (5b), and piperidine (8) is described. Cross-metathesis of optically pure (S)-1-O-benzoyl-3-butene-1,2-diol (2) with protected 4-pentenol, 5-hexenol, and 5-hexenylamine gave the corresponding ally! alcohols (3a), (3b), and (7) in one step, respectively. PdCl(2)(MeCN)(2) catalyzed cyclization of 4a, 4b, and 7 afforded 5a, 5b, and 8 in excellent yields with high enantiomeric purity.

  DOI：

  10.3987/com-09-s(s)95
• 作为产物：
  描述：

  (2S,3E)-8-(tert-butyldimethylsilyloxy)-2-hydroxyoct-3-enyl benzoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到(2S,3E)-2,8-dihydroxyoct-3-enyl benzoate
  参考文献：
  名称：

  A Short Access to Chiral Non-Racemic Oxa- and Azaheterocycles by Cross-Metathesis and Pd-Catalyzed Cyclization Sequence

  摘要：

  A concise synthesis of chiral non-racemic 2-(3-benzoyloxyprop-1-enyl)tetrahydrofuran (5a), tetrahydropyran (5b), and piperidine (8) is described. Cross-metathesis of optically pure (S)-1-O-benzoyl-3-butene-1,2-diol (2) with protected 4-pentenol, 5-hexenol, and 5-hexenylamine gave the corresponding ally! alcohols (3a), (3b), and (7) in one step, respectively. PdCl(2)(MeCN)(2) catalyzed cyclization of 4a, 4b, and 7 afforded 5a, 5b, and 8 in excellent yields with high enantiomeric purity.

  DOI：

  10.3987/com-09-s(s)95