9,10-双(1-羟甲基)蒽-9,10-内过氧化物 | 659746-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 9,10-双(1-羟甲基)蒽-9,10-内过氧化物
• 英文名称: 9,10-bis(1-hydroxymethyl)anthracene-9,10-endoperoxide
• 英文别名: 1-[8-(1-Hydroxyethyl)-15,16-dioxatetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaen-1-yl]ethanol
• CAS: 659746-21-1
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: FBOMMRRZQUYZSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基碘化镁 、 9,10-双(1-羟甲基)蒽-9,10-内过氧化物 以 四氢呋喃 、 乙醚 为溶剂， 以81%的产率得到蒽醌
  参考文献：
  名称：

  Endoperoxidation of 9,10-Bis-(1-hydroxyalkyl)anthracenes and Successive Formation of 9,10-Anthraquinone under Grignard Reaction Conditions

  摘要：

  The reaction of anthracene-9,10-carboaldehyde with various Grignard reagents under ambient conditions gave 9,10-bis(1-hydroxyalkyl)anthracene-9,10-peroxides and 9,10-anthraquinone as the first example. The endoperoxidation of 9,10-bis(1-hydroxyalkyl)anthracenes was assisted by the lone paired electron of oxygen in the side chain, and the endoperoxides were transformed to anthraquinone by the Grignard reagents.

  DOI：

  10.3987/com-03-s(p)24
• 作为产物：
  描述：

  9,10-二(1-羟甲基)蒽 在 氧气 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 9,10-双(1-羟甲基)蒽-9,10-内过氧化物
  参考文献：
  名称：

  Endoperoxidation of 9,10-Bis-(1-hydroxyalkyl)anthracenes and Successive Formation of 9,10-Anthraquinone under Grignard Reaction Conditions

  摘要：

  The reaction of anthracene-9,10-carboaldehyde with various Grignard reagents under ambient conditions gave 9,10-bis(1-hydroxyalkyl)anthracene-9,10-peroxides and 9,10-anthraquinone as the first example. The endoperoxidation of 9,10-bis(1-hydroxyalkyl)anthracenes was assisted by the lone paired electron of oxygen in the side chain, and the endoperoxides were transformed to anthraquinone by the Grignard reagents.

  DOI：

  10.3987/com-03-s(p)24

文献信息

• Endoperoxidation of 9,10-Bis-(1-hydroxyalkyl)anthracenes and Successive Formation of 9,10-Anthraquinone under Grignard Reaction Conditions
  作者：Shigeyasu Kuroda、Mitsunori Oda、Hiroki Syumiya、Shah M. I. Shaheen、Ryuta Miyatake、Teruhiko Nishikawa、Akiko Yoneda、Tokiko Tanaka、Masaru Mouri、Mayumi Kyogoku

  DOI：10.3987/com-03-s(p)24

  日期：——

  The reaction of anthracene-9,10-carboaldehyde with various Grignard reagents under ambient conditions gave 9,10-bis(1-hydroxyalkyl)anthracene-9,10-peroxides and 9,10-anthraquinone as the first example. The endoperoxidation of 9,10-bis(1-hydroxyalkyl)anthracenes was assisted by the lone paired electron of oxygen in the side chain, and the endoperoxides were transformed to anthraquinone by the Grignard reagents.