9,9'-dihydroxy-3,3',4,4'-tetramethoxy-1,1'-bis(methoxymethoxy)-6,6',7,7',10,10a,10',10'a-octahydro-[2,2'-bianthracene]-8,8'(5H,5'H)-dione | 1462394-12-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 9,9'-dihydroxy-3,3',4,4'-tetramethoxy-1,1'-bis(methoxymethoxy)-6,6',7,7',10,10a,10',10'a-octahydro-[2,2'-bianthracene]-8,8'(5H,5'H)-dione
• 英文别名: 9-hydroxy-7-[9-hydroxy-3,4-dimethoxy-1-(methoxymethoxy)-8-oxo-6,7,10,10a-tetrahydro-5H-anthracen-2-yl]-5,6-dimethoxy-8-(methoxymethoxy)-3,4,4a,10-tetrahydro-2H-anthracen-1-one
• CAS: 1462394-12-2
• 化学式: C₃₆H₄₂O₁₂
• 分子量: 666.722
• InChiKey: ISMVHFRNGSUDHC-UHFFFAOYSA-N

物化性质

• 沸点：
  737.7±60.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  Methyl 2-hydroxy-3-(2-hydroxy-5,6-dimethoxy-3-methoxycarbonyl-4-methylphenyl)-4,5-dimethoxy-6-methylbenzoate 在 正丁基锂 、 二异丙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 19.17h， 生成 9,9'-dihydroxy-3,3',4,4'-tetramethoxy-1,1'-bis(methoxymethoxy)-6,6',7,7',10,10a,10',10'a-octahydro-[2,2'-bianthracene]-8,8'(5H,5'H)-dione
  参考文献：
  名称：

  Synthetic Studies on the Bis-Anthraquinoid Core of the Angelimicins

  摘要：

  Bidirectional Hauser and Michael-Dieckmann annulation strategies for the preparation of bis-anthraquinoid framework of the angelimicin family of natural products are explored, using cyclohex-2-enone and biphenyl Michael donors, which are prepared from 1,2,5-trimethoxy-3-methylbenzene. The Hauser annulations are not productive, but the Michael-Dieckmann reactions proceed in 40% yield. Attempts to aromatize these biphenyl cycloadducts proved unsuccessful. This result differs from the success reported in another study of the same reaction. In contrast, aromatization of the related monomeric Michael-Dieckmann cycloadduct proceeds smoothly.

  DOI：

  10.1055/s-0033-1339281

文献信息

• Synthetic Studies on the Bis-Anthraquinoid Core of the Angelimicins
  作者：David Mootoo、Jialiang Li

  DOI：10.1055/s-0033-1339281

  日期：——

  Bidirectional Hauser and Michael-Dieckmann annulation strategies for the preparation of bis-anthraquinoid framework of the angelimicin family of natural products are explored, using cyclohex-2-enone and biphenyl Michael donors, which are prepared from 1,2,5-trimethoxy-3-methylbenzene. The Hauser annulations are not productive, but the Michael-Dieckmann reactions proceed in 40% yield. Attempts to aromatize these biphenyl cycloadducts proved unsuccessful. This result differs from the success reported in another study of the same reaction. In contrast, aromatization of the related monomeric Michael-Dieckmann cycloadduct proceeds smoothly.