5-Methyl-3-[1-(3,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-dihydro-furan-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-Methyl-3-[1-(3,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-dihydro-furan-2-one
• 英文别名: 5-methyl-3-(3,4,5-trimethoxybenzylidene)dihydro-2(3H)-furanone；(3E)-5-methyl-3-[(3,4,5-trimethoxyphenyl)methylidene]oxolan-2-one
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: LGUNFGFMMBPBAX-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl (E)-2-(3,4,5-trimethoxybenzylidene)pent-4-enoate 在 硫酸 作用下， 反应 1.5h， 以91%的产率得到5-Methyl-3-[1-(3,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-dihydro-furan-2-one
  参考文献：
  名称：

  Efficient Synthesis of α ‐Benzylidene‐ γ ‐methyl‐ γ ‐butyrolactones

  摘要：

  A concise synthesis of alpha-benzylidene-gamma-methyl-gamma-butylolactones 5a-g from substituted benzaldehydes is described. Compounds la-g on reaction with phosphorane 2, provide the pentenoates 3a-g, which can be hydrolyzed to the acids 4a-g. The latter are cyclized to the corresponding butyrolactones 5a-g in excellent yields. The pentenoates 3a-g, on acid catalyzed cyclization, also provide 5a-g in very high yields.

  DOI：

  10.1002/1522-2675(200210)85:10<3525::aid-hlca3525>3.0.co;2-#

文献信息

• Efficient Synthesis of <i>α</i> ‐Benzylidene‐ <i>γ</i> ‐methyl‐ <i>γ</i> ‐butyrolactones
  作者：Raghao S. Mali、Kantipudi N. Babu

  DOI：10.1002/1522-2675(200210)85:10<3525::aid-hlca3525>3.0.co;2-#

  日期：2002.10

  A concise synthesis of alpha-benzylidene-gamma-methyl-gamma-butylolactones 5a-g from substituted benzaldehydes is described. Compounds la-g on reaction with phosphorane 2, provide the pentenoates 3a-g, which can be hydrolyzed to the acids 4a-g. The latter are cyclized to the corresponding butyrolactones 5a-g in excellent yields. The pentenoates 3a-g, on acid catalyzed cyclization, also provide 5a-g in very high yields.