1-hydroxy-3-[4-(2-methyl-[1,3]dioxolan-2-yl)-3-oxobutyl]-9,10-anthraquinone | 203498-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-hydroxy-3-[4-(2-methyl-[1,3]dioxolan-2-yl)-3-oxobutyl]-9,10-anthraquinone
• 英文别名: 1-Hydroxy-3-[4-(2-methyl-1,3-dioxolan-2-yl)-3-oxobutyl]anthracene-9,10-dione
• CAS: 203498-69-5
• 化学式: C₂₂H₂₀O₆
• 分子量: 380.397
• InChiKey: HWQNVKWEBGUKGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-hydroxy-3-[4-(2-methyl-[1,3]dioxolan-2-yl)-3-oxobutyl]-9,10-anthraquinone 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 二异丙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 9.0h， 生成 2-bromo-1-methoxy-3-[4-(2-methyl-[1,3]dioxolan-2-yl)-3-oxobutyl]-9,10-anthraquinone
  参考文献：
  名称：

  Biomimetic-Type Synthesis of Benzo[a]naphthacenequinones Related to Pradimicinone

  摘要：

  DOI：

  10.1021/jo9918089
• 作为产物：
  描述：

  3-bromomethyl-1-(2,2-dimethylpropionyloxy)-9,10-anthraquinone 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.83h， 生成 1-hydroxy-3-[4-(2-methyl-[1,3]dioxolan-2-yl)-3-oxobutyl]-9,10-anthraquinone
  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.
• Biomimetic-Type Synthesis of Benzo[<i>a</i>]naphthacenequinones Related to Pradimicinone
  作者：Karsten Krohn、Sven Bernhard、Ulrich Flörke、Nasir Hayat

  DOI：10.1021/jo9918089

  日期：2000.5.1