[(2S,4E,6R)-1-[2-(2-phenylethyl)-1,3-dioxolan-2-yl]-6-prop-2-enoyloxynona-4,8-dien-2-yl] prop-2-enoate | 1257148-78-9

• 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,4E,6R)-1-[2-(2-phenylethyl)-1,3-dioxolan-2-yl]-6-prop-2-enoyloxynona-4,8-dien-2-yl] prop-2-enoate
• CAS: 1257148-78-9
• 化学式: C₂₆H₃₂O₆
• 分子量: 440.536
• InChiKey: CQWVXUHZWQYYMQ-PNTBWQCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S,4E,6R)-1-[2-(2-phenylethyl)-1,3-dioxolan-2-yl]-6-prop-2-enoyloxynona-4,8-dien-2-yl] prop-2-enoate 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以63%的产率得到[(E,2S)-5-[(2R)-6-oxo-2,3-dihydropyran-2-yl]-1-[2-(2-phenylethyl)-1,3-dioxolan-2-yl]pent-4-en-2-yl] prop-2-enoate
  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：

  (2S,4E,6R)-1-[2-(2-phenylethyl)-1,3-dioxolan-2-yl]nona-4,8-diene-2,6-diol 、 丙烯酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到[(2S,4E,6R)-1-[2-(2-phenylethyl)-1,3-dioxolan-2-yl]-6-prop-2-enoyloxynona-4,8-dien-2-yl] prop-2-enoate
  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.