Flavoskyrin | 39546-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Flavoskyrin
• 英文别名: (−)-flavoskyrin
• CAS: 39546-16-2；115729-00-5
• 化学式: C₃₀H₂₄O₁₀
• 分子量: 544.515
• InChiKey: FHQKRPOCCFXEMC-GJXVZKDGSA-N

物化性质

• 熔点：
  215 °C
• 沸点：
  897.8±65.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  40.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  181.82
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Flavoskyrin 生成 大黄酚
  参考文献：
  名称：

  Howard; Raistrick, Biochemical Journal, 1954, vol. 56, p. 54,57, 62

  摘要：

  DOI：
• 作为产物：
  描述：

  大黄素 在 glucose dehydrogenase 、 sodium dithionite 、 可得然胶 、 乙二胺四乙酸 、 L-1,4-二硫代苏糖醇 、 氧气 、 nicotinamide adenine dinucleotide phosphate 、 anthrol reductase from Talaromyces islandicus 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 、 乙腈 为溶剂， 反应 24.0h， 生成 Flavoskyrin
  参考文献：
  名称：

  Synthesis of (−)-Flavoskyrins by Catalyst-Free Oxidation of (R)-Configured Dihydroanthracenones in Aqueous Media and Its (Bio)synthetic Implications

  摘要：

  A catalyst-free method for the synthesis of dimeric (-)-flavoskyrins has been developed. It involves the autoxidation of chemoenzymatically synthesized (R)-configured dihydroanthracenones in the presence of molecular oxygen in buffer of pH 6.0 followed by spontaneous [4 + 2] cycloaddition in stereocontrolled exo-anti fashion to form (-)-flavoskyrins. The method is applied to obtain several homo- as well as heterodimerized flavoskyrins (nine examples) in 27-72% yield and implies the involvement of a similar pathway in the (bio)synthesis of modified bisanthraquinones and their analogues.

  DOI：

  10.1021/acs.orglett.0c03121

文献信息

• Shibata et al., Pharmaceutical Bulletin, 1956, vol. 4, p. 303,308
  作者：Shibata et al.

  DOI：——

  日期：——
• Howard; Raistrick, Biochemical Journal, 1954, vol. 56, p. 54,57, 62
  作者：Howard、Raistrick

  DOI：——

  日期：——
• Synthesis of (−)-Flavoskyrins by Catalyst-Free Oxidation of (<i>R</i>)-Configured Dihydroanthracenones in Aqueous Media and Its (Bio)synthetic Implications
  作者：Amit Mondal、Arijit De、Syed Masood Husain

  DOI：10.1021/acs.orglett.0c03121

  日期：2020.11.6

  A catalyst-free method for the synthesis of dimeric (-)-flavoskyrins has been developed. It involves the autoxidation of chemoenzymatically synthesized (R)-configured dihydroanthracenones in the presence of molecular oxygen in buffer of pH 6.0 followed by spontaneous [4 + 2] cycloaddition in stereocontrolled exo-anti fashion to form (-)-flavoskyrins. The method is applied to obtain several homo- as well as heterodimerized flavoskyrins (nine examples) in 27-72% yield and implies the involvement of a similar pathway in the (bio)synthesis of modified bisanthraquinones and their analogues.