(4R)-4-benzyl-3-[(3E)-(3,7-dimethylocta-3,6-dienoyl)]-oxazolidin-2-one | 364337-20-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4R)-4-benzyl-3-[(3E)-(3,7-dimethylocta-3,6-dienoyl)]-oxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-[(3E)-3,7-dimethylocta-3,6-dienoyl]-1,3-oxazolidin-2-one
• CAS: 364337-20-2
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: WTOMZCSOOHVLKD-QJKHOBJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-4-benzyl-3-[(3E)-(3,7-dimethylocta-3,6-dienoyl)]-oxazolidin-2-one 在 4-二甲氨基吡啶 、 三甲基铝 、 四丁基高碘酸铵 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 、 甲苯 为溶剂， 反应 18.25h， 生成 (4S,5E)-4-[(1S,2R)-2-p-methoxybenzyloxy-1-trimethylsilyloxy-but-3-enyl]-5,9-dimethyl-deca-1,5,8-trienone
  参考文献：
  名称：

  A New, Ring Closing Metathesis-Based Synthesis of (−)-Fumagillol

  摘要：

  [GRAPHICS]A new strategy to access the fumagillin/fumagillol skeleton is proposed. An Evans aldolization and a RCM involving an enone are used for the preparation of a key cyclohexanone intermediate, which was readily converted to fumagillol. The synthesis also features an efficient preparation of isogeraniol and isogeranic acid.

  DOI：

  10.1021/ol016343z
• 作为产物：
  描述：

  E-isogeranic acid 在 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.83h， 生成 (4R)-4-benzyl-3-[(3E)-(3,7-dimethylocta-3,6-dienoyl)]-oxazolidin-2-one
  参考文献：
  名称：

  A New, Ring Closing Metathesis-Based Synthesis of (−)-Fumagillol

  摘要：

  [GRAPHICS]A new strategy to access the fumagillin/fumagillol skeleton is proposed. An Evans aldolization and a RCM involving an enone are used for the preparation of a key cyclohexanone intermediate, which was readily converted to fumagillol. The synthesis also features an efficient preparation of isogeraniol and isogeranic acid.

  DOI：

  10.1021/ol016343z

文献信息

• A New, Ring Closing Metathesis-Based Synthesis of (−)-Fumagillol
  作者：Jean-Guy Boiteau、Pierre Van de Weghe、Jacques Eustache

  DOI：10.1021/ol016343z

  日期：2001.8.1

  [GRAPHICS]A new strategy to access the fumagillin/fumagillol skeleton is proposed. An Evans aldolization and a RCM involving an enone are used for the preparation of a key cyclohexanone intermediate, which was readily converted to fumagillol. The synthesis also features an efficient preparation of isogeraniol and isogeranic acid.