(E)-3-butyl-5-(4-cyanophenyl)-2-(methoxycarbonyl)-2,4-pentadienoic acid methyl ester | 1444004-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-butyl-5-(4-cyanophenyl)-2-(methoxycarbonyl)-2,4-pentadienoic acid methyl ester
• 英文别名: dimethyl 2-[(E)-1-(4-cyanophenyl)hept-1-en-3-ylidene]propanedioate
• CAS: 1444004-45-8
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: IVCOKAQGCIZUNJ-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dimethyl 2-butylcycloprop-2-ene-1,1-dicarboxylate 、 4-氰基苯甲醛 在 三(4-甲氧苯基)膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 30.0h， 以68%的产率得到(E)-3-butyl-5-(4-cyanophenyl)-2-(methoxycarbonyl)-2,4-pentadienoic acid methyl ester
  参考文献：
  名称：

  Unexpected Regioselectivity Switch: Organophosphine-Triggered Reactions of Cyclopropene-1,1-dicarboxylates with Aldehydes

  摘要：

  With tris(4-methoxyphenyl)phosphine as the nucleophilic reagent, the readily available cyclopropene-1,1-dicarboxylates undergo a ring-opening reaction to generate a Wittig-type intermediate, which would react with aromatic aldehydes to yield (E)-5-aryl-2-(methoxycarbonyl)-2,4-pentadienoates. It is interesting to observe that the regioselectivity of the ring-opening reaction is switched.

  DOI：

  10.1021/ol401324z

文献信息

• Unexpected Regioselectivity Switch: Organophosphine-Triggered Reactions of Cyclopropene-1,1-dicarboxylates with Aldehydes
  作者：Shengjun Ni、Jie Chen、Shengming Ma

  DOI：10.1021/ol401324z

  日期：2013.7.5

  With tris(4-methoxyphenyl)phosphine as the nucleophilic reagent, the readily available cyclopropene-1,1-dicarboxylates undergo a ring-opening reaction to generate a Wittig-type intermediate, which would react with aromatic aldehydes to yield (E)-5-aryl-2-(methoxycarbonyl)-2,4-pentadienoates. It is interesting to observe that the regioselectivity of the ring-opening reaction is switched.