(E)-4-(3-methoxyphenyl)but-2-enoic acid | 137744-85-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-4-(3-methoxyphenyl)but-2-enoic acid
• CAS: 137744-85-5
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: DJRAEYKXANMEOO-XVNBXDOJSA-N

物化性质

• 沸点：
  371.2±30.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  间溴苯甲醚 、 巴豆酸 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 生成 (E)-4-(3-methoxyphenyl)but-3-enoic acid 、 (E)-4-(3-methoxyphenyl)but-2-enoic acid
  参考文献：
  名称：

  Reaction of 2-butenoic acid dianion and its N-(4-methoxyphenyl)amide with methoxy-substituted arynes

  摘要：

  N-(4-Methoxyphenyl)-1-butenamide dianion (6), generated by the reaction of N-(4-methoxyphenyl)-2-butenamide (3) with LDA or LTMP, undergoes exclusive 4-arylation with various methoxy-substituted arynes 2a-e yielding mixtures consisting of a N-(4-methoxyphenyl)-(E)-4-aryl-3-butenamide 9 (85-90%) and a N-(4-methoxyphenyl)-(E)-4-aryl-2-butenamide 9' (10-15%). Under certain conditions, 4,4-diarylated products 12 are also obtained. 2-Butenoic acid dianion (14) also reacts with methoxy-substituted arynes affording predominantly 4-aryl-3-butenoic acids 15 and minor amounts of 4-aryl-2-butenoic acids 15'. The exclusive low temperature (-30 to -40-degrees-C) 4-addition of arynes to dianion 14 is in contrast to the predominant 2-addition that 14 undergoes with certain aldehydes and ketones at comparable temperatures. The mixtures of 4-arylbutenoic acids 15 and 15' and 4-arylbutenamides 9 and 9' were readily hydrogenated (Pd/C) and esterified (MeOH/H2SO4) to synthetically valuable methyl 4-arylbutanoates 17.

  DOI：

  10.1021/jo00028a049

文献信息

• Reaction of 2-butenoic acid dianion and its N-(4-methoxyphenyl)amide with methoxy-substituted arynes
  作者：Abdul Rakeeb Deshmukh、Tran Long、Edward R. Biehl

  DOI：10.1021/jo00028a049

  日期：1992.1

  N-(4-Methoxyphenyl)-1-butenamide dianion (6), generated by the reaction of N-(4-methoxyphenyl)-2-butenamide (3) with LDA or LTMP, undergoes exclusive 4-arylation with various methoxy-substituted arynes 2a-e yielding mixtures consisting of a N-(4-methoxyphenyl)-(E)-4-aryl-3-butenamide 9 (85-90%) and a N-(4-methoxyphenyl)-(E)-4-aryl-2-butenamide 9' (10-15%). Under certain conditions, 4,4-diarylated products 12 are also obtained. 2-Butenoic acid dianion (14) also reacts with methoxy-substituted arynes affording predominantly 4-aryl-3-butenoic acids 15 and minor amounts of 4-aryl-2-butenoic acids 15'. The exclusive low temperature (-30 to -40-degrees-C) 4-addition of arynes to dianion 14 is in contrast to the predominant 2-addition that 14 undergoes with certain aldehydes and ketones at comparable temperatures. The mixtures of 4-arylbutenoic acids 15 and 15' and 4-arylbutenamides 9 and 9' were readily hydrogenated (Pd/C) and esterified (MeOH/H2SO4) to synthetically valuable methyl 4-arylbutanoates 17.