(R)-5-((4E,8E)-(R)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one | 862556-86-3

• 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)-5-((4E,8E)-(R)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one
• 英文别名: (5R)-5-[(1R,4E,8E)-1-hydroxy-12-phenylmethoxydodeca-4,8-dienyl]oxolan-2-one
• CAS: 862556-86-3
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: ABJPJQDYNQRJGD-HGRFSFRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-5-((4E,8E)-(R)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one 在 D-fructose-based (-)-Shi catalyst 、 四丁基硫酸氢铵 Sodium tetraborate decahydrate 、 Oxone 、 sodium hydroxide 、 偶氮二甲酸二异丙酯 、 camphor-10-sulfonic acid 、 potassium carbonate 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 27.5h， 生成 (2R,2'R,5'S,2''R,5''S)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one
  参考文献：
  名称：

  A Bidirectional Approach to the Synthesis of a Complete Library of Adjacent-Bis-THF Annonaceous Acetogenins

  摘要：

  Thirty-six stereoisomers of bifunctional adjacent bis-THF (tetrahydrofuran) lactones have been synthesized, which can afford a complete library of the adjacent bis-THF Annonaceous acetogenins. The bis-THF lactones were synthesized, starting from the enantioselectively pure 8,9:12,13-(E,E and Z,E)-16-benzyloxy-5-hydroxy-hexadeca-1,4-olide, in a highly distereoselective manner using oxidative reactions, including rhenium(VII) oxides-mediated oxidative cyclization, Shi's asymmetric epoxidation, and Sharpless asymmetric dihydroxylation reactions. Using the nonsymmetrical bis-THF lactones, syntheses of two nonnatural acetogenins were achieved.

  DOI：

  10.1021/jo050697c
• 作为产物：
  描述：

  (R)-5-((4E,8E)-(S)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one 在 sodium hydroxide 、 偶氮二甲酸二异丙酯 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (R)-5-((4E,8E)-(R)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one
  参考文献：
  名称：

  A Bidirectional Approach to the Synthesis of a Complete Library of Adjacent-Bis-THF Annonaceous Acetogenins

  摘要：

  Thirty-six stereoisomers of bifunctional adjacent bis-THF (tetrahydrofuran) lactones have been synthesized, which can afford a complete library of the adjacent bis-THF Annonaceous acetogenins. The bis-THF lactones were synthesized, starting from the enantioselectively pure 8,9:12,13-(E,E and Z,E)-16-benzyloxy-5-hydroxy-hexadeca-1,4-olide, in a highly distereoselective manner using oxidative reactions, including rhenium(VII) oxides-mediated oxidative cyclization, Shi's asymmetric epoxidation, and Sharpless asymmetric dihydroxylation reactions. Using the nonsymmetrical bis-THF lactones, syntheses of two nonnatural acetogenins were achieved.

  DOI：

  10.1021/jo050697c