[(E,3S)-1-oxo-6-[(2R)-6-oxo-2,3-dihydropyran-2-yl]hex-5-en-3-yl] prop-2-enoate | 1257148-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: [(E,3S)-1-oxo-6-[(2R)-6-oxo-2,3-dihydropyran-2-yl]hex-5-en-3-yl] prop-2-enoate
• CAS: 1257148-69-8
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: HWNUTQBNFFPXAO-SCBUBVSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  magnesium,ethylbenzene,bromide 、 [(E,3S)-1-oxo-6-[(2R)-6-oxo-2,3-dihydropyran-2-yl]hex-5-en-3-yl] prop-2-enoate 以 四氢呋喃 为溶剂， 反应 1.0h， 以4 mg的产率得到(2R)-2-[(E,4S,6R)-4,6-dihydroxy-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
• 作为产物：
  描述：

  [(E,3S)-1,1-dimethoxy-6-[(2R)-6-oxo-2,3-dihydropyran-2-yl]hex-5-en-3-yl] prop-2-enoate 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 [(E,3S)-1-oxo-6-[(2R)-6-oxo-2,3-dihydropyran-2-yl]hex-5-en-3-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.