1-naphthylhydroxycyclopropenone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-naphthylhydroxycyclopropenone
• 英文别名: 2-Hydroxy-3-naphthalen-1-ylcycloprop-2-en-1-one；2-hydroxy-3-naphthalen-1-ylcycloprop-2-en-1-one
• 化学式: C₁₃H₈O₂
• 分子量: 196.205
• InChiKey: FHUNIVMNSPLANH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-naphthylhydroxycyclopropenone 在 水 作用下， 生成 1-萘乙酸
  参考文献：
  名称：

  Flash Photolytic Generation and Study of Ynolate Ions and the Corresponding Ketenes in Aqueous Solution

  摘要：

  Flash photolysis of a series of arylhydroxycyclopropenones (aryl = phenyl, mesityl, 4-methoxyphenyl, 2,4,6-trimethoxyphenyl, and 1-naphthyl) in aqueous solution was found to give arylacetic acids as final products through two successively formed, short-lived reaction intermediates. Rate profiles, the form of acid-base catalysis, and solvent isotope effects identified the first of these intermediates as arylynolate ions, ArC=CO-, and the second as arylketenes, ArCH=C=O; the identity of the ketenes was also confirmed by independent generation through photo-Wolff reaction of corresponding aryl diazo compounds. The kinetic behavior of the arylynolate ions shows that the corresponding arylynols, ArC=COH, are remarkably strong acids, with pK(a) < 3.

  DOI：

  10.1021/ja00141a007

文献信息

• Flash Photolytic Generation and Study of Ynolate Ions and the Corresponding Ketenes in Aqueous Solution
  作者：Y. Chiang、A. J. Kresge、V. V. Popik

  DOI：10.1021/ja00141a007

  日期：1995.9

  Flash photolysis of a series of arylhydroxycyclopropenones (aryl = phenyl, mesityl, 4-methoxyphenyl, 2,4,6-trimethoxyphenyl, and 1-naphthyl) in aqueous solution was found to give arylacetic acids as final products through two successively formed, short-lived reaction intermediates. Rate profiles, the form of acid-base catalysis, and solvent isotope effects identified the first of these intermediates as arylynolate ions, ArC=CO-, and the second as arylketenes, ArCH=C=O; the identity of the ketenes was also confirmed by independent generation through photo-Wolff reaction of corresponding aryl diazo compounds. The kinetic behavior of the arylynolate ions shows that the corresponding arylynols, ArC=COH, are remarkably strong acids, with pK(a) < 3.