(3S*,4S*)-3-allyl-4-vinyldihydrofuran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S*,4S*)-3-allyl-4-vinyldihydrofuran-2-one
• 英文别名: (3S,4S)-4-ethenyl-3-prop-2-enyloxolan-2-one
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: FUORAYVUBUISBH-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S*,4S*)-3-allyl-4-vinyldihydrofuran-2-one 在 Grubbs catalyst first generation 吡啶 、 咪唑 、 disodium hydrogenphosphate 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 (1S,2E,4Z,7E)-1-ethyl-8-{(1R,2S,3S,5S)-3-[(S)-6-oxotetrahydropyran-2-yl]-6-oxabicyclo[3.1.0]hex-2-yl}octa-2,4,7-trienyl acetate
  参考文献：
  名称：

  Synthesis and structural revision of marine eicosanoid agardhilactone

  摘要：

  Synthesis of the marine eicosanoid agardhilactone has been achieved. The relative and absolute configuration of agardhilactone was successfully determined. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.102
• 作为产物：
  描述：

  4-乙烯基二氢呋喃-2(3H)-酮 、 丙烯酰碘 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以74%的产率得到(3S*,4S*)-3-allyl-4-vinyldihydrofuran-2-one
  参考文献：
  名称：

  Synthesis of Marine Oxylipin Agardhilactone and Its Analogues: A Structural Revision

  摘要：

  Synthesis of four analogues of the marine oxylipin agardhilactone was carried out. The relative configuration of agardhilactone was determined by comparison with agardhilactone acetate and four analogues. Furthermore, synthesis of agardhilactone was achieved. The absolute configuration of agardhilactone was successfully determined by this synthesis.

  DOI：

  10.3987/com-08-s(f)97

文献信息

• Synthesis of Marine Oxylipin Agardhilactone and Its Analogues: A Structural Revision
  作者：Hiroaki Miyaoka、Etsuko Kawashima、Yoshinori Hara、Ikuo Shinohara、Takao Kurokawa、Yasuji Yamada

  DOI：10.3987/com-08-s(f)97

  日期：——

  Synthesis of four analogues of the marine oxylipin agardhilactone was carried out. The relative configuration of agardhilactone was determined by comparison with agardhilactone acetate and four analogues. Furthermore, synthesis of agardhilactone was achieved. The absolute configuration of agardhilactone was successfully determined by this synthesis.
• Synthesis and structural revision of marine eicosanoid agardhilactone
  作者：Hiroaki Miyaoka、Yoshinori Hara、Ikuo Shinohara、Takao Kurokawa、Yasuji Yamada

  DOI：10.1016/j.tetlet.2005.09.102

  日期：2005.11

  Synthesis of the marine eicosanoid agardhilactone has been achieved. The relative and absolute configuration of agardhilactone was successfully determined. (c) 2005 Elsevier Ltd. All rights reserved.