(R)-(E)-5-(3-hydroxypropyl)-3-(prop-1-enyl)furan-2(5H)-one | 950994-91-9

• 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: (R)-(E)-5-(3-hydroxypropyl)-3-(prop-1-enyl)furan-2(5H)-one
• 英文别名: (2R)-2-(3-hydroxypropyl)-4-[(E)-prop-1-enyl]-2H-furan-5-one
• CAS: 950994-91-9
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: PWMCIAJEOBUFFF-HDMKULJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(E)-5-(3-hydroxypropyl)-3-(prop-1-enyl)furan-2(5H)-one 在 (IMes)CuCl 、 三苯基膦 、 异丙醇 、 2-碘酰基苯甲酸 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 (-)-pregaliellalactone
  参考文献：
  名称：

  Copper-Catalyzed Methylenation Reaction:  Total Synthesis of (+)-Desoxygaliellalactone

  摘要：

  The enantioselective total synthesis of (+)-desoxygaliellalactone was achieved in six steps starting from 4-tert-butyldimethylsilyloxybutanal. This synthesis featured a one-pot copper-catalyzed methylenation-Diels-Alder cyclization. The challenging methylenation of aldehyde 4 was studied under various reaction conditions. Whereas Wittig reaction conditions led to byproducts resulting from decomposition of the sensitive butenolide moiety, the mild copper-catalyzed methylenation reaction produced the desired triene in good yield.

  DOI：

  10.1021/ol071391q
• 作为产物：
  描述：

  ethyl 7-(tert-butyldimethylsilyloxy)-4-hydroxyhept-2-ynoate 在 四(三苯基膦)钯 碘 、 三正丁基氢锡 、 乙酰氯 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 为溶剂， 反应 16.0h， 生成 (R)-(E)-5-(3-hydroxypropyl)-3-(prop-1-enyl)furan-2(5H)-one
  参考文献：
  名称：

  Copper-Catalyzed Methylenation Reaction:  Total Synthesis of (+)-Desoxygaliellalactone

  摘要：

  The enantioselective total synthesis of (+)-desoxygaliellalactone was achieved in six steps starting from 4-tert-butyldimethylsilyloxybutanal. This synthesis featured a one-pot copper-catalyzed methylenation-Diels-Alder cyclization. The challenging methylenation of aldehyde 4 was studied under various reaction conditions. Whereas Wittig reaction conditions led to byproducts resulting from decomposition of the sensitive butenolide moiety, the mild copper-catalyzed methylenation reaction produced the desired triene in good yield.

  DOI：

  10.1021/ol071391q

文献信息

• Copper-Catalyzed Methylenation Reaction:  Total Synthesis of (+)-Desoxygaliellalactone
  作者：Hélène Lebel、Michaël Parmentier

  DOI：10.1021/ol071391q

  日期：2007.8.1

  The enantioselective total synthesis of (+)-desoxygaliellalactone was achieved in six steps starting from 4-tert-butyldimethylsilyloxybutanal. This synthesis featured a one-pot copper-catalyzed methylenation-Diels-Alder cyclization. The challenging methylenation of aldehyde 4 was studied under various reaction conditions. Whereas Wittig reaction conditions led to byproducts resulting from decomposition of the sensitive butenolide moiety, the mild copper-catalyzed methylenation reaction produced the desired triene in good yield.