ethyl (E)-2-((4-chlorophenoxy)methyl)but-2-enoate | 1296202-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl (E)-2-((4-chlorophenoxy)methyl)but-2-enoate
• CAS: 1296202-34-0
• 化学式: C₁₃H₁₅ClO₃
• 分子量: 254.713
• InChiKey: GFWDYRRLTGETJA-XCVCLJGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  ethyl 2-methylbuta-2,3-dienoate 、 对氯苯酚 在 三苯基膦 作用下， 以 苯 为溶剂， 反应 17.0h， 以62%的产率得到ethyl (E)-2-((4-chlorophenoxy)methyl)but-2-enoate
  参考文献：
  名称：

  Phosphine-Catalyzed β′-Umpolung Addition of Nucleophiles to Activated α-Alkyl Allenes

  摘要：

  Highly function alized alkenes can be prepared through phosphine-catalyzed beta'-umpolung additions of nucleophiles (carbon-, oxygen-, nitrogen-, and sulfur-centered) to activated alpha-disubstituted allenes, providing many potentially useful synthetic intermediates in good to excellent yields, often with high levels of stereoselectivity for the product olefin geometry. Various substitution patterns around the allene are compatible with the process, showcasing the synthetic utility of allenes under the conditions of nucleophilic phosphine catalysis.

  DOI：

  10.1021/ol200697m

文献信息

• Phosphane-Catalyzed Umpolung Addition Reaction of Nucleophiles to Ethyl 2-Methyl-2,3-butadienoate
  作者：Xiao-Yang Guan、Yin Wei、Min Shi

  DOI：10.1002/ejoc.201100095

  日期：2011.5

  phosphane-catalyzed umpolung addition of various nucleophiles to ethyl 2-methyl-2,3-butadienoate is described. Oxygen, nitrogen, and carbon nucleophiles smoothly reacted with ethyl 2-methyl-2,3-butadienoate to give the corresponding umpolung addition products in good to excellent yields by a similar reaction mechanism. For sulfur nucleophiles, the addition reactions with ethyl 2-methyl-2,3-butadienoate proceeded

  描述了磷烷催化的各种亲核试剂对 2-甲基-2,3-丁二烯酸乙酯的umpolung 加成。氧、氮和碳亲核试剂与 2-甲基-2,3-丁二烯酸乙酯顺利反应，通过类似的反应机理以良好至极好的产率得到相应的 umpolung 加成产物。对于硫亲核试剂，与 2-甲基-2,3-丁二烯酸乙酯的加成反应通过不同的机制进行。