1-Methoxy-2-benzyl-9,10-anthraquinone | 171816-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-Methoxy-2-benzyl-9,10-anthraquinone
• 英文别名: 2-Benzyl-1-methoxyanthracene-9,10-dione
• CAS: 171816-08-3
• 化学式: C₂₂H₁₆O₃
• 分子量: 328.367
• InChiKey: LVGWUGDDCLSCES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  1-Methoxy-2-benzyl-9,10-anthraquinone 以 甲醇 为溶剂， 生成 2-benzyl-1-hydroxy-9,10-anthraquinone
  参考文献：
  名称：

  Photochemistry of 1-alkoxy- and 1-(benzyloxy)-9,10-anthraquinones in methanol: A facile process for the preparation of aldehydes and ketones

  摘要：

  The facile production of acid sensitive aldehydes and ketones via photochemical intramolecular delta-hydrogen atom transfer in 1-alkoxy- and 1-(benzyloxy)-9,10-anthraquinones (1) was investigated. Irradiation of 1 in argon purged methanol generates the primary photoproducts, 1-(RCH(OMe)O)-and 1-(ArCH(OMe)O)-9,10-antharahydroquinones (2), respectively. Upon exposure to air, the intermediate anthrahydroquinone is rapidly converted to the corresponding aldehyde and 1-hydroxy-9,10-anthraquinone (3), which can be recycled. Aldehydes containing an acetal or ketal were prepared in high yields using this photoprocess. Apparent rate constants for the photodemethylation of 1-methoxy-2-X-9,10-anthraquinones (X = H, Me, Et, Pr, Bu, i-Bu, and benzyl) were measured and found to vary by a factor of 10 separating the slowest anthraquinone (X = H) and the fastest (X = benzyl), indicating a strong dependency upon the size of the substituent at the a-position. These rate constants are ascribed to equilibrium populations of confonmers in the geometry required for reaction in the n,pi* triplet state.

  DOI：

  10.1021/jo00126a040
• 作为产物：
  描述：

  2-Benzyl-1-[[4-(1,3-dioxolan-2-yl)phenyl]-methoxymethoxy]anthracene-9,10-diol 在 air 作用下， 生成 1-Methoxy-2-benzyl-9,10-anthraquinone
  参考文献：
  名称：

  Photochemistry of 1-alkoxy- and 1-(benzyloxy)-9,10-anthraquinones in methanol: A facile process for the preparation of aldehydes and ketones

  摘要：

  The facile production of acid sensitive aldehydes and ketones via photochemical intramolecular delta-hydrogen atom transfer in 1-alkoxy- and 1-(benzyloxy)-9,10-anthraquinones (1) was investigated. Irradiation of 1 in argon purged methanol generates the primary photoproducts, 1-(RCH(OMe)O)-and 1-(ArCH(OMe)O)-9,10-antharahydroquinones (2), respectively. Upon exposure to air, the intermediate anthrahydroquinone is rapidly converted to the corresponding aldehyde and 1-hydroxy-9,10-anthraquinone (3), which can be recycled. Aldehydes containing an acetal or ketal were prepared in high yields using this photoprocess. Apparent rate constants for the photodemethylation of 1-methoxy-2-X-9,10-anthraquinones (X = H, Me, Et, Pr, Bu, i-Bu, and benzyl) were measured and found to vary by a factor of 10 separating the slowest anthraquinone (X = H) and the fastest (X = benzyl), indicating a strong dependency upon the size of the substituent at the a-position. These rate constants are ascribed to equilibrium populations of confonmers in the geometry required for reaction in the n,pi* triplet state.

  DOI：

  10.1021/jo00126a040

文献信息

• Photochemistry of 1-alkoxy- and 1-(benzyloxy)-9,10-anthraquinones in methanol: A facile process for the preparation of aldehydes and ketones
  作者：Ronald L. Blankespoor、Robert P. Smart、Eric D. Batts、Alan A. Kiste、Rebecca E. Lew、Marc E. Van der Vliet

  DOI：10.1021/jo00126a040

  日期：1995.10

  The facile production of acid sensitive aldehydes and ketones via photochemical intramolecular delta-hydrogen atom transfer in 1-alkoxy- and 1-(benzyloxy)-9,10-anthraquinones (1) was investigated. Irradiation of 1 in argon purged methanol generates the primary photoproducts, 1-(RCH(OMe)O)-and 1-(ArCH(OMe)O)-9,10-antharahydroquinones (2), respectively. Upon exposure to air, the intermediate anthrahydroquinone is rapidly converted to the corresponding aldehyde and 1-hydroxy-9,10-anthraquinone (3), which can be recycled. Aldehydes containing an acetal or ketal were prepared in high yields using this photoprocess. Apparent rate constants for the photodemethylation of 1-methoxy-2-X-9,10-anthraquinones (X = H, Me, Et, Pr, Bu, i-Bu, and benzyl) were measured and found to vary by a factor of 10 separating the slowest anthraquinone (X = H) and the fastest (X = benzyl), indicating a strong dependency upon the size of the substituent at the a-position. These rate constants are ascribed to equilibrium populations of confonmers in the geometry required for reaction in the n,pi* triplet state.