2-[1-(4-Benzyloxy-phenyl)-meth-(E)-ylidene]-pent-4-enoic acid | 502180-42-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-[1-(4-Benzyloxy-phenyl)-meth-(E)-ylidene]-pent-4-enoic acid
• 英文别名: (2E)-2-[(4-phenylmethoxyphenyl)methylidene]pent-4-enoic acid
• CAS: 502180-42-9
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: XMKDNQYXYIKSMK-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2-[1-(4-Benzyloxy-phenyl)-meth-(E)-ylidene]-pent-4-enoic acid 在 硫酸 作用下， 反应 1.5h， 以92%的产率得到3-[1-(4-Benzyloxy-phenyl)-meth-(E)-ylidene]-5-methyl-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-#
• 作为产物：
  描述：

  ethyl 2-(triphenyl-λ⁵-phosphanylidene)pent-4-enoate 在 氢氧化钾 、 silica gel 作用下， 以 乙醇 为溶剂， 反应 6.12h， 生成 2-[1-(4-Benzyloxy-phenyl)-meth-(E)-ylidene]-pent-4-enoic acid
  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.