4-Anthracen-9-yl-butan-2-one | 103130-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-Anthracen-9-yl-butan-2-one
• 英文别名: 4-Anthracen-9-ylbutan-2-one
• CAS: 103130-86-5
• 化学式: C₁₈H₁₆O
• 分子量: 248.324
• InChiKey: JWGFCQZSYSBJQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-Anthracen-9-yl-butan-2-one 以 异丙醇 为溶剂， 以54%的产率得到(3S,3aS)-3-Methyl-2,3,3a,6,7,11b-hexahydro-1H-benzo[de]anthracen-3-ol
  参考文献：
  名称：

  Electroreductive intramolecular coupling of nonconjugated aromatic ketones

  摘要：

  The electroreduction of nonconjugated aromatic ketones gave intramolecularly coupled products. The best result was obtained using an Sn cathode in i-PrOH containing tetraalkylammonium salt as a supporting electrolyte. This reductive cyclization proceeded with remarkable stereoselectivity, and the cis isomer was obtained exclusively. A variety of new bi- and polycyclic compounds were synthesized. The reaction mechanism was studied, and it was suggested that the anion radical generated by one-electron transfer to a carbonyl group attacks an aromatic ring intramolecularly. The choice of counter cation of the anion radical was critical for the reductive cyclization. Other reductive methods employing metal reducing agents were also studied. Reduction with Na in HMPA-THF gave the same cyclized product, though the yield was lower than that with the electroreduction.

  DOI：

  10.1021/jo00085a033
• 作为产物：
  描述：

  9-溴甲基蒽 、 乙酰乙酸乙酯 生成 4-Anthracen-9-yl-butan-2-one
  参考文献：
  名称：

  Electroreductive intramolecular coupling of nonconjugated aromatic ketones

  摘要：

  The electroreduction of nonconjugated aromatic ketones gave intramolecularly coupled products. The best result was obtained using an Sn cathode in i-PrOH containing tetraalkylammonium salt as a supporting electrolyte. This reductive cyclization proceeded with remarkable stereoselectivity, and the cis isomer was obtained exclusively. A variety of new bi- and polycyclic compounds were synthesized. The reaction mechanism was studied, and it was suggested that the anion radical generated by one-electron transfer to a carbonyl group attacks an aromatic ring intramolecularly. The choice of counter cation of the anion radical was critical for the reductive cyclization. Other reductive methods employing metal reducing agents were also studied. Reduction with Na in HMPA-THF gave the same cyclized product, though the yield was lower than that with the electroreduction.

  DOI：

  10.1021/jo00085a033

文献信息

• Electroorganic chemistry. 98. Novel intramolecular stereoselective addition of electrogenerated radical species to the aromatic ring
  作者：Tatsuya. Shono、Naoki. Kise、Takeshi. Suzumoto、Toshio. Morimoto

  DOI：10.1021/ja00275a084

  日期：1986.7

  La reduction electrochimique de derives de l'aryl-5 pentanone-2 conduit a des derives de l'(hexahydro-1,2,3,4,6,8a methyl-1) naphtol-1

  La 还原电化学 de 衍生 de l'aryl-5 pentanone-2 导管 a des 衍生 de l'(hexahydro-1,2,3,4,6,8amethyl-1)naphtol-1
• Deacylative Thiolation by Redox‐Neutral Aromatization‐Driven C−C Fragmentation of Ketones
  作者：Xukai Zhou、Daniel Pyle、Zining Zhang、Guangbin Dong

  DOI：10.1002/anie.202213691

  日期：2023.4.3

  A redox-neutral, heavy-metal-free approach has been developed to realize deacylative thiolation of common ketones, which provides a unique method to introduce thioether groups site-specifically to unactivated aliphatic positions. Experimental and computational mechanistic studies suggest the involvement of a radical chain pathway.

  开发了一种氧化还原中性、无重金属的方法来实现常见酮的脱酰硫醇化，这提供了一种将硫醚基团位点特异性引入到未活化的脂肪族位置的独特方法。实验和计算机制研究表明自由基链途径的参与。