9,9'-dihydroxy-1,1',3,3',4,4'-hexamethoxy-6,6',7,7',10,10a,10',10'a-octahydro-2,2'-bianthracene-8,8'(5H,5'H)-dione

• 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-1,1',3,3',4,4'-hexamethoxy-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-1,3,4-trimethoxy-8-oxo-6,7,10,10a-tetrahydro-5H-anthracen-2-yl)-5,6,8-trimethoxy-3,4,4a,10-tetrahydro-2H-anthracen-1-one
• 化学式: C₃₄H₃₈O₁₀
• 分子量: 606.67
• InChiKey: ACSYVBFQCRBWBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  44
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  9,9'-dihydroxy-1,1',3,3',4,4'-hexamethoxy-6,6',7,7',10,10a,10',10'a-octahydro-2,2'-bianthracene-8,8'(5H,5'H)-dione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 5.0h， 以40%的产率得到9,9'-dihydroxy-1,1',3,3',4,4'-hexamethoxy-6,6',7,7'-tetrahydro-2,2'-bianthracene-8,8'(5H,5'H)-dione
  参考文献：
  名称：

  Assignment and Stereocontrol of Hibarimicin Atropoisomers

  摘要：

  A stereochemical feature of the hibarimicins is a central biaryl (HMP-Y6) or aryl-quinone (hibarimicinone) incorporated as a single atropodiastereomer. Herein, a chiral resolution and deracemization process to access optically enriched biaryls aR-3 and aS-3 is described. From these atropoenantiomers the BCD-EFG ring system of HMP-Y6 is constructed [(+)-aR-7]. Comparison of CD spectra of aR-7 to HMP-Y6 leads to the assignment of HMP-Y6 and hibarimicin B atropoisomers as aR and aS, respectively.

  DOI：

  10.1021/ol2017005
• 作为产物：
  描述：

  1,2,5-三甲氧基-3-甲基苯 在 sodium chlorite 、 sodium dihydrogenphosphate 、 正丁基锂 、 2,3-二甲基-2-丁烯 、 双氧水 、 四氯化钛 、 铜 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 41.0h， 生成 9,9'-dihydroxy-1,1',3,3',4,4'-hexamethoxy-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.
• Assignment and Stereocontrol of Hibarimicin Atropoisomers
  作者：Ian M. Romaine、Jonathan E. Hempel、Ganesh Shanmugam、Hiroshi Hori、Yasuhiro Igarashi、Prasad L. Polavarapu、Gary A. Sulikowski

  DOI：10.1021/ol2017005

  日期：2011.9.2

  A stereochemical feature of the hibarimicins is a central biaryl (HMP-Y6) or aryl-quinone (hibarimicinone) incorporated as a single atropodiastereomer. Herein, a chiral resolution and deracemization process to access optically enriched biaryls aR-3 and aS-3 is described. From these atropoenantiomers the BCD-EFG ring system of HMP-Y6 is constructed [(+)-aR-7]. Comparison of CD spectra of aR-7 to HMP-Y6 leads to the assignment of HMP-Y6 and hibarimicin B atropoisomers as aR and aS, respectively.