(2R)-2-[(E,4S)-4-hydroxy-6-oxo-8-phenyloct-1-enyl]-2,3-dihydropyran-6-one | 1257148-58-5

• 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: (2R)-2-[(E,4S)-4-hydroxy-6-oxo-8-phenyloct-1-enyl]-2,3-dihydropyran-6-one
• CAS: 1257148-58-5
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: YGRDFGLHIMEZAD-LXCLZNAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  (2R)-2-[(E,4S)-4-hydroxy-6-oxo-8-phenyloct-1-enyl]-2,3-dihydropyran-6-one 在 tetramethylammonium triacetoxyborohydride 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 10.5h， 以91%的产率得到(R)-6-((4S,6S,E)-4,6-dihydroxy-8-phenyloct-1-en-1-yl)-5,6-dihydro-2H-pyran-2-one-(+)-strictifolione
  参考文献：
  名称：

  Concise Total Syntheses of (+)-Strictifolione and (6R)-6-[(4R,6R)-4,6-Dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one

  摘要：

  Concise and efficient asymmetric total syntheses of (+)-strictifolione 1 and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one 2 have been achieved based on the strategic application of one-pot double allylboration and ring-closing metathesis reactions. The total syntheses proceeded in only five and seven steps, respectively, from readily available 3-butenal and represent the shortest syntheses of 1 and 2 reported to date.

  DOI：

  10.1021/jo101875w
• 作为产物：
  描述：

  在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以49 mg的产率得到(2R)-2-[(E,4S)-4-hydroxy-6-oxo-8-phenyloct-1-enyl]-2,3-dihydropyran-6-one
  参考文献：
  名称：

  Concise Total Syntheses of (+)-Strictifolione and (6R)-6-[(4R,6R)-4,6-Dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one

  摘要：

  Concise and efficient asymmetric total syntheses of (+)-strictifolione 1 and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one 2 have been achieved based on the strategic application of one-pot double allylboration and ring-closing metathesis reactions. The total syntheses proceeded in only five and seven steps, respectively, from readily available 3-butenal and represent the shortest syntheses of 1 and 2 reported to date.

  DOI：

  10.1021/jo101875w