dimethyl (5S,5′S,6R,6′R,10aS,10a′S)-1,1′,5,5′,8,8′-hexahydroxy-6,6′-dimethyl-9,9′-dioxo-5,5′,6,6′,7,7′,9,9′-octahydro-10aH,10a′H-[4,4′-bixanthene]-10a,10a′-dicarboxylate | 2615-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: dimethyl (5S,5′S,6R,6′R,10aS,10a′S)-1,1′,5,5′,8,8′-hexahydroxy-6,6′-dimethyl-9,9′-dioxo-5,5′,6,6′,7,7′,9,9′-octahydro-10aH,10a′H-[4,4′-bixanthene]-10a,10a′-dicarboxylate
• 英文别名: Secalonsaeure A
• CAS: 2615-62-5
• 化学式: C₃₂H₃₀O₁₄
• 分子量: 638.582
• InChiKey: ISZKIEBUBOALCU-ZKHWAINJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  46.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  226.58
• 氢给体数：
  6.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  dimethyl (5S,5′S,6R,6′R,10aS,10a′S)-1,1′,5,5′,8,8′-hexahydroxy-6,6′-dimethyl-9,9′-dioxo-5,5′,6,6′,7,7′,9,9′-octahydro-10aH,10a′H-[4,4′-bixanthene]-10a,10a′-dicarboxylate 以 二甲基亚砜 为溶剂， 反应 13.0h， 生成 secalonic acid A 、 penicillixanthone A
  参考文献：
  名称：

  Syntheses of Dimeric Tetrahydroxanthones with Varied Linkages: Investigation of “Shapeshifting” Properties

  摘要：

  The 2,4'- and 4,4'-linked variants of the cytotoxic agent secalonic acid A and their analogues have been synthesized. Kinetic resolution of an unprotected tetrahydroxanthone scaffold followed by copper-mediated biaryl coupling allowed for efficient access to these compounds. Evaluation of the "shapeshifting" properties of 2,2'-, 2,4'-, and 4,4'-linked variants of the secalonic acids A in a polar solvent in conjunction with assays of the compounds against select cancer cell lines was conducted to study possible correlations between linkage variation and cytotoxicity.

  DOI：

  10.1021/jacs.5b09825
• 作为产物：
  描述：

  在 盐酸 、 copper(l) chloride 、 copper dichloride 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 12.5h， 生成 dimethyl (5S,5′S,6R,6′R,10aS,10a′S)-1,1′,5,5′,8,8′-hexahydroxy-6,6′-dimethyl-9,9′-dioxo-5,5′,6,6′,7,7′,9,9′-octahydro-10aH,10a′H-[4,4′-bixanthene]-10a,10a′-dicarboxylate
  参考文献：
  名称：

  Syntheses of Dimeric Tetrahydroxanthones with Varied Linkages: Investigation of “Shapeshifting” Properties

  摘要：

  The 2,4'- and 4,4'-linked variants of the cytotoxic agent secalonic acid A and their analogues have been synthesized. Kinetic resolution of an unprotected tetrahydroxanthone scaffold followed by copper-mediated biaryl coupling allowed for efficient access to these compounds. Evaluation of the "shapeshifting" properties of 2,2'-, 2,4'-, and 4,4'-linked variants of the secalonic acids A in a polar solvent in conjunction with assays of the compounds against select cancer cell lines was conducted to study possible correlations between linkage variation and cytotoxicity.

  DOI：

  10.1021/jacs.5b09825