5-Hydroxy-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-2,3-dihydro-1H-cyclopenta[a]anthracene-6,11-dione | 203499-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 5-Hydroxy-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-2,3-dihydro-1H-cyclopenta[a]anthracene-6,11-dione
• 英文别名: 5-hydroxy-1-[(2-methyl-1,3-dioxolan-2-yl)methyl]-2,3-dihydro-1H-cyclopenta[a]anthracene-6,11-dione
• CAS: 203499-13-2
• 化学式: C₂₂H₂₀O₅
• 分子量: 364.398
• InChiKey: MOPALQWZLFPISH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Hydroxy-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-2,3-dihydro-1H-cyclopenta[a]anthracene-6,11-dione 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到5-Hydroxy-1-(2-oxo-propyl)-2,3-dihydro-1H-cyclopenta[a]anthracene-6,11-dione
  参考文献：
  名称：

  Reductive Cyclization of (3-) and (4-Oxoalkyl)-9,10-anthraquinones to the cyclopenta[a]anthraquinone and naphthacene-5,12-dione systems

  摘要：

  Reductive cyclization of the 1-hydroxy-3-(3-oxoalkyl)-9,10-anthraquinones 2, 9 and 10 yields the angularly condensed cyclopenta[a]anthraquinones 3, 21 and 22a under neutral conditions (DMF/Na2S2O4). By contrast, the linear cyclopenta[b]anthraquinone 23 is isolated from 10 applying the usual alkaline Marschalk conditions (aqueous methanol, NaOH, Na2S2O4). The linearly condensed 5,12-naphthacenequinones 24-28 of different degree of saturation are obtained in good combined yield from the corresponding 1-hydroxy-3-(4-oxoalkyl)-9,10-anthraquinones 19 and 20 under the conditions of the Marschalk reaction.

  DOI：

  10.1002/prac.19983400105
• 作为产物：
  描述：

  2-[4-(2,2-Dimethyl-propionyloxy)-9,10-dioxo-9,10-dihydro-anthracen-2-ylmethyl]-4-(2-methyl-[1,3]dioxolan-2-yl)-3-oxo-butyric acid methyl ester 在 sodium hydroxide 、 sodium dithionite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.33h， 生成 5-Hydroxy-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-2,3-dihydro-1H-cyclopenta[a]anthracene-6,11-dione
  参考文献：
  名称：

  Reductive Cyclization of (3-) and (4-Oxoalkyl)-9,10-anthraquinones to the cyclopenta[a]anthraquinone and naphthacene-5,12-dione systems

  摘要：

  Reductive cyclization of the 1-hydroxy-3-(3-oxoalkyl)-9,10-anthraquinones 2, 9 and 10 yields the angularly condensed cyclopenta[a]anthraquinones 3, 21 and 22a under neutral conditions (DMF/Na2S2O4). By contrast, the linear cyclopenta[b]anthraquinone 23 is isolated from 10 applying the usual alkaline Marschalk conditions (aqueous methanol, NaOH, Na2S2O4). The linearly condensed 5,12-naphthacenequinones 24-28 of different degree of saturation are obtained in good combined yield from the corresponding 1-hydroxy-3-(4-oxoalkyl)-9,10-anthraquinones 19 and 20 under the conditions of the Marschalk reaction.

  DOI：

  10.1002/prac.19983400105

文献信息

• Reductive Cyclization of (3-) and (4-Oxoalkyl)-9,10-anthraquinones to the cyclopenta[a]anthraquinone and naphthacene-5,12-dione systems
  作者：Karsten Krohn、Sven Bernhard

  DOI：10.1002/prac.19983400105

  日期：——

  Reductive cyclization of the 1-hydroxy-3-(3-oxoalkyl)-9,10-anthraquinones 2, 9 and 10 yields the angularly condensed cyclopenta[a]anthraquinones 3, 21 and 22a under neutral conditions (DMF/Na2S2O4). By contrast, the linear cyclopenta[b]anthraquinone 23 is isolated from 10 applying the usual alkaline Marschalk conditions (aqueous methanol, NaOH, Na2S2O4). The linearly condensed 5,12-naphthacenequinones 24-28 of different degree of saturation are obtained in good combined yield from the corresponding 1-hydroxy-3-(4-oxoalkyl)-9,10-anthraquinones 19 and 20 under the conditions of the Marschalk reaction.