(2S)-4-hex-1-ynyl-2-methyl-2H-furan-5-one | 1571081-75-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (2S)-4-hex-1-ynyl-2-methyl-2H-furan-5-one
• CAS: 1571081-75-8
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: RLEFXASAVMORPF-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  (2S)-4-hex-1-ynyl-2-methyl-2H-furan-5-one 在 吡啶 、 5% palladium on barium sulphate 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、303.99 kPa 条件下， 反应 8.0h， 以88%的产率得到(1'Z,5S)-3-(1-hexenyl)-5-methylfuran-2(5H)-one
  参考文献：
  名称：

  Short, Enantioselective Total Syntheses of Fugomycin and Desoxyfugomycin via Sonogashira Alkynylation of α-Bromobutenolides

  摘要：

  The potent antifungal antibiotics (+)-fugomycin and (+)-desoxyfugomycin were synthesized in 3-4 steps with high overall efficiency (51-53%) and optical purity (ee > 97%). The syntheses illustrate a highly effective protocol for accomplishing racemization-free Sonogashira coupling of chiral -bromobutenolides, and the usefulness of the Movassaghi-Jacobsen method for preparing the latter from epoxides.

  DOI：

  10.1055/s-0033-1339926
• 作为产物：
  描述：

  (S)-3-bromo-5-methylfuran-2(5H)-one 、 1-己炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.33h， 以79%的产率得到(2S)-4-hex-1-ynyl-2-methyl-2H-furan-5-one
  参考文献：
  名称：

  Short, Enantioselective Total Syntheses of Fugomycin and Desoxyfugomycin via Sonogashira Alkynylation of α-Bromobutenolides

  摘要：

  The potent antifungal antibiotics (+)-fugomycin and (+)-desoxyfugomycin were synthesized in 3-4 steps with high overall efficiency (51-53%) and optical purity (ee > 97%). The syntheses illustrate a highly effective protocol for accomplishing racemization-free Sonogashira coupling of chiral -bromobutenolides, and the usefulness of the Movassaghi-Jacobsen method for preparing the latter from epoxides.

  DOI：

  10.1055/s-0033-1339926

文献信息

• Short, Enantioselective Total Syntheses of Fugomycin and Desoxyfugomycin via Sonogashira Alkynylation of α-Bromobutenolides
  作者：John Boukouvalas、Nicolas Bruneau-Latour

  DOI：10.1055/s-0033-1339926

  日期：——

  The potent antifungal antibiotics (+)-fugomycin and (+)-desoxyfugomycin were synthesized in 3-4 steps with high overall efficiency (51-53%) and optical purity (ee > 97%). The syntheses illustrate a highly effective protocol for accomplishing racemization-free Sonogashira coupling of chiral -bromobutenolides, and the usefulness of the Movassaghi-Jacobsen method for preparing the latter from epoxides.