ethyl 3-vinyl-2-naphthoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 3-vinyl-2-naphthoate
• 英文别名: Ethyl 3-ethenylnaphthalene-2-carboxylate；ethyl 3-ethenylnaphthalene-2-carboxylate
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: PFEIWANJLIAQSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙基戊-2,3-二烯酸酯 、 邻苯二甲醛 在 乙基二苯基膦 作用下， 以 甲苯 为溶剂， 以97%的产率得到ethyl 3-vinyl-2-naphthoate
  参考文献：
  名称：

  Phosphine-Mediated Iterative Arene Homologation Using Allenes

  摘要：

  A PPh3-mediated multicomponent reaction between o-phthalaldehydes, nucleophiles, and monosubstituted allenes furnishes functionalized non-C-2-symmetric naphthalenes in synthetically useful yields. When the o-phthalaldehydes were reacted with 1,3-disubstituted allenes in the presence of PPh2Et, naphthalene derivatives were also obtained in up to quantitative yields. The mechanism of the latter transformation is straightforward: aldol addition followed by Wittig olefination and dehydration. The mechanism of the former is a tandem gamma-umpolung/aldol/Wittig/dehydration process, as established by preparation of putative reaction intermediates and mass spectrometric analysis. This transformation can be applied iteratively to prepare anthracenes and tetracenes using carboxylic acids as pronucleophiles.

  DOI：

  10.1021/jacs.5b07403

文献信息

• Phosphine-Mediated Iterative Arene Homologation Using Allenes
  作者：Kui Zhang、Lingchao Cai、Xing Jiang、Miguel A. Garcia-Garibay、Ohyun Kwon

  DOI：10.1021/jacs.5b07403

  日期：2015.9.9

  A PPh3-mediated multicomponent reaction between o-phthalaldehydes, nucleophiles, and monosubstituted allenes furnishes functionalized non-C-2-symmetric naphthalenes in synthetically useful yields. When the o-phthalaldehydes were reacted with 1,3-disubstituted allenes in the presence of PPh2Et, naphthalene derivatives were also obtained in up to quantitative yields. The mechanism of the latter transformation is straightforward: aldol addition followed by Wittig olefination and dehydration. The mechanism of the former is a tandem gamma-umpolung/aldol/Wittig/dehydration process, as established by preparation of putative reaction intermediates and mass spectrometric analysis. This transformation can be applied iteratively to prepare anthracenes and tetracenes using carboxylic acids as pronucleophiles.