2-[1-(4-Benzyloxy-phenyl)-meth-(E)-ylidene]-pent-4-enoic acid ethyl ester | 502180-35-0

• 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 ethyl ester
• 英文别名: ethyl (2E)-2-[(4-phenylmethoxyphenyl)methylidene]pent-4-enoate
• CAS: 502180-35-0
• 化学式: C₂₁H₂₂O₃
• 分子量: 322.404
• InChiKey: VFHCZIPLZYWTDD-XDJHFCHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 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 ethyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以91%的产率得到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-#
• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 ethyl 2-(triphenyl-λ⁵-phosphanylidene)pent-4-enoate 在 silica gel 作用下， 反应 0.12h， 以96%的产率得到2-[1-(4-Benzyloxy-phenyl)-meth-(E)-ylidene]-pent-4-enoic acid ethyl ester
  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.