3-(acetoxymethyl)-3,4-dihydro-9,10-dihydroxy-8-methoxy-6-methyl-1(2H)-anthracenone | 864846-02-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-(acetoxymethyl)-3,4-dihydro-9,10-dihydroxy-8-methoxy-6-methyl-1(2H)-anthracenone
• 英文别名: (9,10-dihydroxy-5-methoxy-7-methyl-4-oxo-2,3-dihydro-1H-anthracen-2-yl)methyl acetate
• CAS: 864846-02-6
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: IBKCHOIETNSULH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(acetoxymethyl)-3,4-dihydro-9,10-dihydroxy-8-methoxy-6-methyl-1(2H)-anthracenone 在 lead(IV) acetate 、 三溴化硼 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 4.83h， 生成 3,4-bis(acetoxymethyl)-3a,3b,4,5-tetrahydro-1,7,8,17-tetrahydroxy-10,15-dimethyl-2H-dibenzo[c,mn]naphtho[2,3-g]xanthene-6,13,18(3H)-trione
  参考文献：
  名称：

  Efficient Syntheses of Rugulosin Analogues

  摘要：

  [GRAPHICS]Oxidation of 3b or 14c,d with Pb(OAc)(4) in AcOH for 20 min at 25 degrees C and 1 h at 75 degrees C gave flavoskyrin-type dimers 6b and 15c,d in 53-86% yield. Heating a solution of 6b or 15c,d in pyridine under air for 1 h at 75-80 degrees C and then for 1-2 h at 110 degrees C afforded rugulosin-type dimers 10b and 17c,d in 61-88% yield. This two-step sequence provides a practical route to this unusual natural product skeleton.

  DOI：

  10.1021/jo0508898
• 作为产物：
  描述：

  N,N-diethyl-2-methoxy-4-methylbenzamide 在 盐酸 、 四甲基乙二胺 、 potassium tert-butylate 、 仲丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 环己烷 、 水 为溶剂， 反应 34.0h， 生成 3-(acetoxymethyl)-3,4-dihydro-9,10-dihydroxy-8-methoxy-6-methyl-1(2H)-anthracenone
  参考文献：
  名称：

  Efficient Syntheses of Rugulosin Analogues

  摘要：

  [GRAPHICS]Oxidation of 3b or 14c,d with Pb(OAc)(4) in AcOH for 20 min at 25 degrees C and 1 h at 75 degrees C gave flavoskyrin-type dimers 6b and 15c,d in 53-86% yield. Heating a solution of 6b or 15c,d in pyridine under air for 1 h at 75-80 degrees C and then for 1-2 h at 110 degrees C afforded rugulosin-type dimers 10b and 17c,d in 61-88% yield. This two-step sequence provides a practical route to this unusual natural product skeleton.

  DOI：

  10.1021/jo0508898

文献信息

• Efficient Syntheses of Rugulosin Analogues
  作者：Barry B. Snider、Xiaolei Gao

  DOI：10.1021/jo0508898

  日期：2005.8.1

  [GRAPHICS]Oxidation of 3b or 14c,d with Pb(OAc)(4) in AcOH for 20 min at 25 degrees C and 1 h at 75 degrees C gave flavoskyrin-type dimers 6b and 15c,d in 53-86% yield. Heating a solution of 6b or 15c,d in pyridine under air for 1 h at 75-80 degrees C and then for 1-2 h at 110 degrees C afforded rugulosin-type dimers 10b and 17c,d in 61-88% yield. This two-step sequence provides a practical route to this unusual natural product skeleton.