1-(9-phenyl-9H-xanthen-9-yl)propan-2-one | 42528-48-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-(9-phenyl-9H-xanthen-9-yl)propan-2-one
• 英文别名: (9-phenyl-xanthen-9-yl)-propan-2-one；1-(9-Phenylxanthen-9-yl)propan-2-one；1-(9-phenylxanthen-9-yl)propan-2-one
• CAS: 42528-48-3
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: WXYHFVGLUFSDKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  9-苯基苯二烯-9-醇 、 丙酮 在 1,2-dipyridinium ditribromide ethane 、 乙酸酐 作用下， 反应 12.0h， 以87%的产率得到1-(9-phenyl-9H-xanthen-9-yl)propan-2-one
  参考文献：
  名称：

  Syntheses and regiochemistry of enol addition to 9-phenyl-9H-xanthen-9-ol

  摘要：

  Regioselective C-C bond formation of 9-phenyl-9H-xanthen-9-ol 1 with various enolizable ketones I-X in an acidic (HBr) medium, obtained by the reaction of 1, 1'-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) with ketone is observed. Except for ketone, 4-methylpentan-2-one VII in all other cases examined the attack to xanthenyl carbocation is from the thermodynamically stable enolizable side of the unsymmetrical ketones. In the case of 3-methyl-butan-2-one VIII the equilibrium is in favor of the more stable enolizable ketone, which has large steric factor, hence no reaction was observed during its addition to alcohol 1. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.053

文献信息

• Syntheses and regiochemistry of enol addition to 9-phenyl-9H-xanthen-9-ol
  作者：Veerababurao Kavala、Siva Murru、Gopal Das、Bhisma K. Patel

  DOI：10.1016/j.tet.2008.02.053

  日期：2008.4

  Regioselective C-C bond formation of 9-phenyl-9H-xanthen-9-ol 1 with various enolizable ketones I-X in an acidic (HBr) medium, obtained by the reaction of 1, 1'-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) with ketone is observed. Except for ketone, 4-methylpentan-2-one VII in all other cases examined the attack to xanthenyl carbocation is from the thermodynamically stable enolizable side of the unsymmetrical ketones. In the case of 3-methyl-butan-2-one VIII the equilibrium is in favor of the more stable enolizable ketone, which has large steric factor, hence no reaction was observed during its addition to alcohol 1. (c) 2008 Elsevier Ltd. All rights reserved.