2-Hydroxybenzochroman-4-one | 23469-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-Hydroxybenzochroman-4-one
• 英文别名: 2-Hydroxy-benzo-chroman-4-on；2-Hydroxy-benzo[f]-chroman-4-on；3-Hydroxy-2,3-dihydrobenzo[f]chromen-1-one
• CAS: 23469-44-5
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: YPCUCYSXIDETTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Hydroxybenzochroman-4-one 在 肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以61%的产率得到3-(2'-Hydroxy-1'-naphthyl)pyrazole
  参考文献：
  名称：

  Toward the Photostability Mechanism of Intramolecular Hydrogen Bond Systems. 4. 3(5)-(1'-Hydroxy-2'-naphthyl)pyrazoles and 3(5)-(2'-Hydroxy-1'-naphthyl)pyrazoles

  摘要：

  Two new families of compounds, the 3(5)-(1'-hydroxy-2'-naphthyl)pyrazoles (a series) and the 3(5)-(2'-hydroxy-1'-naphthyl)pyrazoles (b series), have been synthesized and fully characterized. The use of NMR (H-1 and C-13) and UV (absorption and emission) spectroscopies in different solvents led us to determine the major tautomers, the coplanarity of both rings (naphthyl and pyrazolyl) if present, and the existence of hydrogen bonds. The photostability of a representative set of such derivatives was also determined, showing that the existence of an intramolecular hydrogen bond (IMHB) is not an essential condition for providing UV stability. Moreover when such an IMHB is present in the molecule, the photostability is not dependent on whether the proton is transferred or not.

  DOI：

  10.1021/jo00116a032
• 作为产物：
  描述：

  1-乙酰基-2-萘酚 、 甲酸乙酯 在 sodium 作用下， 以 乙醚 为溶剂， 以85%的产率得到2-Hydroxybenzochroman-4-one
  参考文献：
  名称：

  Toward the Photostability Mechanism of Intramolecular Hydrogen Bond Systems. 4. 3(5)-(1'-Hydroxy-2'-naphthyl)pyrazoles and 3(5)-(2'-Hydroxy-1'-naphthyl)pyrazoles

  摘要：

  Two new families of compounds, the 3(5)-(1'-hydroxy-2'-naphthyl)pyrazoles (a series) and the 3(5)-(2'-hydroxy-1'-naphthyl)pyrazoles (b series), have been synthesized and fully characterized. The use of NMR (H-1 and C-13) and UV (absorption and emission) spectroscopies in different solvents led us to determine the major tautomers, the coplanarity of both rings (naphthyl and pyrazolyl) if present, and the existence of hydrogen bonds. The photostability of a representative set of such derivatives was also determined, showing that the existence of an intramolecular hydrogen bond (IMHB) is not an essential condition for providing UV stability. Moreover when such an IMHB is present in the molecule, the photostability is not dependent on whether the proton is transferred or not.

  DOI：

  10.1021/jo00116a032