(2R,4E,6S)-1-[2-(4-phenylbutyl)-1,3-dioxolan-2-yl]nona-4,8-diene-2,6-diol | 1257148-82-5

• 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,4E,6S)-1-[2-(4-phenylbutyl)-1,3-dioxolan-2-yl]nona-4,8-diene-2,6-diol
• CAS: 1257148-82-5
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: FKCREYSTYKEFFV-BGTMZHHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4E,6S)-1-[2-(4-phenylbutyl)-1,3-dioxolan-2-yl]nona-4,8-diene-2,6-diol 在 4-甲基苯磺酸吡啶 作用下， 以 水 、 丙酮 为溶剂， 反应 5.0h， 以91%的产率得到(7R,9E,11S)-7,11-dihydroxy-1-phenyltetradeca-9,13-dien-5-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
• 作为产物：
  描述：

  3-丁烯醛 、 2-[2-(4-Phenylbutyl)-1,3-dioxolan-2-yl]acetaldehyde 、 以 乙醚 为溶剂， 反应 2.0h， 以52%的产率得到(2R,4E,6S)-1-[2-(4-phenylbutyl)-1,3-dioxolan-2-yl]nona-4,8-diene-2,6-diol
  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

文献信息

• Concise Total Syntheses of (+)-Strictifolione and (6<i>R</i>)-6-[(4<i>R</i>,6<i>R</i>)-4,6-Dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2<i>H</i>-pyran-2-one
  作者：Shibing Tang、Xingang Xie、Xiaolei Wang、Liuer He、Ke Xu、Xuegong She

  DOI：10.1021/jo101875w

  日期：2010.12.3

  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.