1-<<<4-(1,3-Dioxolan-2-yl)>benzyl>oxy>-2-benzyl-9,10-anthraquinone | 171815-97-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-<<<4-(1,3-Dioxolan-2-yl)>benzyl>oxy>-2-benzyl-9,10-anthraquinone
• 英文别名: 2-Benzyl-1-[[4-(1,3-dioxolan-2-yl)phenyl]methoxy]anthracene-9,10-dione
• CAS: 171815-97-7
• 化学式: C₃₁H₂₄O₅
• 分子量: 476.529
• InChiKey: OAFWZTJWLKXOEP-UHFFFAOYSA-N

物化性质

• 沸点：
  707.2±60.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-<<<4-(1,3-Dioxolan-2-yl)>benzyl>oxy>-2-benzyl-9,10-anthraquinone 在 air 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 4-(1,3-二氧杂环戊烷-2-基)-苯甲醛
  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：

  1-(甲氧基(苯基)甲氧基)-2-甲基蒽-9,10-二醇 在 sodium hydroxide 、 sodium dithionite 、 air 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.17h， 生成 1-<<<4-(1,3-Dioxolan-2-yl)>benzyl>oxy>-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