3-(p-tosyloxy)phenalen-1-one | 946148-13-6

• 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-(p-tosyloxy)phenalen-1-one
• 英文别名: (3-Oxophenalen-1-yl) 4-methylbenzenesulfonate
• CAS: 946148-13-6
• 化学式: C₂₀H₁₄O₄S
• 分子量: 350.395
• InChiKey: JDYVYVQCKKCHME-UHFFFAOYSA-N

物化性质

• 沸点：
  563.7±50.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(p-tosyloxy)phenalen-1-one 在 sodium tetrahydroborate 、 lanthanum chloride heptahydrate 、 硫酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以11%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

文献信息

• A New Method of Synthesizing Phenalen-1-one: Reduction of 3-Hydroxyphenalen-1-one Using NaBH₄ and Lanthanoid Chlorides
  作者：Tadanobu Sawada、Hiroyuki Ishii、Toyotoshi Ueda、Junji Aoki

  DOI：10.1080/00397910902883546

  日期：2009.10.12

  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.