3-Acetoxy-1-oxo-phenalen | 18931-04-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 非那烯类
• 英文名称: 3-Acetoxy-1-oxo-phenalen
• 英文别名: 3-acetoxyphenalen-1-one；(3-Oxophenalen-1-yl) acetate
• CAS: 18931-04-9
• 化学式: C₁₅H₁₀O₃
• 分子量: 238.243
• InChiKey: ZMSFZRZAZNZPGW-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C(Solv: benzene (71-43-2))
• 沸点：
  426.9±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Acetoxy-1-oxo-phenalen 在 sodium tetrahydroborate 、 lanthanum chloride heptahydrate 、 硫酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以45.3%的产率得到萘嵌苯酮
  参考文献：
  名称：

  A New Method of Synthesizing Phenalen-1-one: Reduction of 3-Hydroxyphenalen-1-one Using NaBH₄ and Lanthanoid Chlorides

  摘要：

  Phenalen-1-one was obtained in considerable yield by reducing 3-hydroxyphenalen-1-one. Most of known preparation methods are not very practical, either because their yields are very poor or because their processes have many steps. This regioselective 1,2-reduction proceeded by the action of NaBH4 and various cations of rare-earth elements and metals. The yields of phenalen-1-one were examined as a function of typical lanthanoids, molar ratios of lanthanoid ions to 3-acetoxy-phenalen-1-one, and differing methods of protecting the hydroxyl group. Lanthanum chloride (LaCl3) gave the greatest yield (45.3%) of phenalen-1-one at molar ratios higher than a third, probably because La3+ ion is a hard acid and coordinates easily to a hard solvent such as methanol. Further, it has the largest ionic radius among all lanthanoid ions.

  DOI：

  10.1080/00397910902883546
• 作为产物：
  描述：

  2,2-dibromo-phenalene-1,3-dione 在 sodium hydroxide 作用下， 生成 3-Acetoxy-1-oxo-phenalen
  参考文献：
  名称：

  Eistert,B. et al., Chemische Berichte, 1968, vol. 101, # 6, p. 2162 - 2175

  摘要：

  DOI：