3-phenylprop-2-ynyl 3-hydroxynaphthalene-2-carboxylate | 1421956-90-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-phenylprop-2-ynyl 3-hydroxynaphthalene-2-carboxylate
• 英文别名: 3-Phenylprop-2-ynyl 3-hydroxynaphthalene-2-carboxylate
• CAS: 1421956-90-2
• 化学式: C₂₀H₁₄O₃
• 分子量: 302.329
• InChiKey: GVNSTLJRFNVVGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  2-羟基-3-萘甲酸 在 碘 、 zinc trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 4.67h， 生成 3-phenylprop-2-ynyl 3-hydroxynaphthalene-2-carboxylate
  参考文献：
  名称：

  Zn(OTf)₂-Promoted Chemoselective Esterification of Hydroxyl Group Bearing Carboxylic Acids

  摘要：

  Selective esterification of aliphatic and aromatic carboxylic acids with various alcohols is studied using triphenylphosphine, I-2, and a catalytic amount of Zn(OTf)(2). Use of this catalyst allows the formation of esters at a faster rate with good to excellent yield by activating the in situ generated acyloxyphosphonium ion intermediate. During the esterification process, both their aromatic and aliphatic hydroxyl groups are fully preserved from trans-esterification. The results show that the bulkiness and the reactivity of this doubly activated intermediate III control the selectivity and the rate of the reaction, respectively. The method is also useful for direct amidation reactions.

  DOI：

  10.1021/jo302502r

文献信息

• Zn(OTf)₂-Promoted Chemoselective Esterification of Hydroxyl Group Bearing Carboxylic Acids
  作者：Narsimha Mamidi、Debasis Manna

  DOI：10.1021/jo302502r

  日期：2013.3.15

  Selective esterification of aliphatic and aromatic carboxylic acids with various alcohols is studied using triphenylphosphine, I-2, and a catalytic amount of Zn(OTf)(2). Use of this catalyst allows the formation of esters at a faster rate with good to excellent yield by activating the in situ generated acyloxyphosphonium ion intermediate. During the esterification process, both their aromatic and aliphatic hydroxyl groups are fully preserved from trans-esterification. The results show that the bulkiness and the reactivity of this doubly activated intermediate III control the selectivity and the rate of the reaction, respectively. The method is also useful for direct amidation reactions.