(5aS,6R,13aS,14R,17S,18R,19R,20S)-7,15-dihydroxy-3,11-dimethoxy-1,9,17,20-tetrakis(methoxymethoxy)-14-hydro-5H,6H-6,13a,5a,14-(epibutane[1,2,3,4]tetrayl)cycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16-tetraone | 875926-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (5aS,6R,13aS,14R,17S,18R,19R,20S)-7,15-dihydroxy-3,11-dimethoxy-1,9,17,20-tetrakis(methoxymethoxy)-14-hydro-5H,6H-6,13a,5a,14-(epibutane[1,2,3,4]tetrayl)cycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16-tetraone
• CAS: 875926-31-1
• 化学式: C₃₈H₃₈O₁₆
• 分子量: 750.71
• InChiKey: HBUFDVNIGJGTKI-BCPJEYGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  54.0
• 可旋转键数：
  14.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  201.04
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (5aS,6R,13aS,14R,17S,18R,19R,20S)-7,15-dihydroxy-3,11-dimethoxy-1,9,17,20-tetrakis(methoxymethoxy)-14-hydro-5H,6H-6,13a,5a,14-(epibutane[1,2,3,4]tetrayl)cycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16-tetraone 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以100%的产率得到
  参考文献：
  名称：

  Total Syntheses of 2,2‘-epi-Cytoskyrin A, Rugulosin, and the Alleged Structure of Rugulin

  摘要：

  The total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin are described. These naturally occurring bisanthraquinones and their relatives are characterized by novel molecular architectures at the core, at which lies a more or less complete, cage-like structural motif termed "skyrane". The strategies developed for their total synthesis feature a cascade sequence called the "cytoskyrin cascade" and deliver these molecules in short order and in a stereoselective manner.

  DOI：

  10.1021/ja0685708
• 作为产物：
  描述：

  4-甲氧基水杨酸 在 4-二甲氨基吡啶 、 N,N-二甲基甲酰胺 potassium cyanide 、 manganese(IV) oxide 、 草酰氯 、 18-冠醚-6 、 四甲基乙二胺 、 四丁基氟化铵 、 叔丁基锂 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 60.17h， 生成 (5aS,6R,13aS,14R,17S,18R,19R,20S)-7,15-dihydroxy-3,11-dimethoxy-1,9,17,20-tetrakis(methoxymethoxy)-14-hydro-5H,6H-6,13a,5a,14-(epibutane[1,2,3,4]tetrayl)cycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16-tetraone
  参考文献：
  名称：

  Total Syntheses of 2,2‘-epi-Cytoskyrin A, Rugulosin, and the Alleged Structure of Rugulin

  摘要：

  The total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin are described. These naturally occurring bisanthraquinones and their relatives are characterized by novel molecular architectures at the core, at which lies a more or less complete, cage-like structural motif termed "skyrane". The strategies developed for their total synthesis feature a cascade sequence called the "cytoskyrin cascade" and deliver these molecules in short order and in a stereoselective manner.

  DOI：

  10.1021/ja0685708

文献信息

• Total Synthesis of (+)-Rugulosin and (+)-2,2′-epi-Cytoskyrin A through Cascade Reactions
  作者：K. C. Nicolaou、Yee Hwee Lim、Charles D. Papageorgiou、Jared L. Piper

  DOI：10.1002/anie.200503678

  日期：2005.12.9