8-amino-3-methylbenz[a]anthracene-7,12-dione | 1176925-45-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 角环素
• 英文名称: 8-amino-3-methylbenz[a]anthracene-7,12-dione
• 英文别名: 8-amino-3-methylbenz[a]anthraquinone；8-Amino-3-methylbenzo[a]anthracene-7,12-dione
• CAS: 1176925-45-3
• 化学式: C₁₉H₁₃NO₂
• 分子量: 287.318
• InChiKey: LYBJCFJKDCDBAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-amino-3-methylbenz[a]anthracene-7,12-dione 、 1,5-Anhydro-3-O-acetyl-2,6-dideoxy-L-arabino-hex-1-enitol 在 indium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以27%的产率得到[(1R,21R,22R,23S)-11,23-dimethyl-6,17-dioxo-24-oxa-20-azahexacyclo[19.3.1.02,19.05,18.07,16.08,13]pentacosa-2(19),3,5(18),7(16),8(13),9,11,14-octaen-22-yl] acetate
  参考文献：
  名称：

  Efficient Synthesis of the Tetracyclic Aminoquinone Moiety of Marmycin A

  摘要：

  An efficient four-step route to the tetracyclic aminoquinone moiety of marmycin A that proceeds in 41% overall yield from 5-nitronaphthoquinone and 5-methyl-1-vinylcyclohexene will facilitate preparation of marmycin A analogues for biological evaluation. The Diels-Alder reaction gave exclusively the desired adduct that is favored by steric considerations rather than the regioisomeric adduct that is favored by electronic considerations.

  DOI：

  10.1021/ol9020496
• 作为产物：
  描述：

  在 盐酸 、 水 、 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以23 mg的产率得到8-amino-3-methylbenz[a]anthracene-7,12-dione
  参考文献：
  名称：

  Mar霉素A的合成研究：C3'-去甲基类似物的制备

  摘要：

  研究了天然产物mar霉素A的全合成。以脱羧烷基化，Pd（OAc）2催化的环化，芳构化和CN偶联为关键步骤，建立了关键片段8-氨基-3-甲基苯并[ a ]蒽醌（1）的快速合成策略。然而，由于无法获得碳水化合物片段2，mar霉素A的最终组装受阻。取而代之的是，使用InBr 3催化的C-和N以适度的产率制备了一个小霉素霉素A的去甲基类似物文库-糖基化反应。这些化合物的绝对构型通过将其光谱数据与with霉素A的光谱数据进行比较，并通过X射线分析得以证实。

  DOI：

  10.1021/jo9011078

文献信息

• InBr₃-Catalyzed Glycosidation of Glycals with Arylamines: An Alternative Approach To Access 4-Aminocyclopent-2-enones
  作者：Fulong Li、Chunyong Ding、Meining Wang、Qizheng Yao、Ao Zhang

  DOI：10.1021/jo200243d

  日期：2011.4.15

  To turn side products into major products, a novel strategy to access biologically active 4-aminocyclopent-2-enones was developed. These compounds were originally identified as side products but became major products when 3,5-dimethylpyran-3,4-diol 7a was used as the substrate and 30% InBr3 as the catalyst. Aryl- or heteroarylamines as well as variously substituted glycals can be used in this reaction, and the corresponding 4-aminocyclopent-2-enones were obtained in moderate to good yields. These compounds can be further used to prepare 4-aminocarbocyclic nucleosides.
• METHOD FOR PREPARING MARMYCIN A AND ANALOGUES THEREOF, AND ALSO USES THEREOF
  申请人：Centre national de la recherche scientifique

  公开号：US20170260210A1

  公开（公告）日：2017-09-14

  The present invention relates to a method for preparing marmycin A and analogues thereof, to novel marmycin A analogues, and also to the use of these compounds as an organelle marker and in pharmacy, in particular as antibiotics, anticancer agents and antimalarials.
• Synthesis Study on Marmycin A: Preparation of the C3′-Desmethyl Analogues
  作者：Chunyong Ding、Shanghui Tu、Fuying Li、Yuanxiang Wang、Qizheng Yao、Wenxiang Hu、Hua Xie、Linghua Meng、Ao Zhang

  DOI：10.1021/jo9011078

  日期：2009.8.21

  Total synthesis of natural product marmycin A was studied. An expeditious synthetic strategy for the key fragment 8-amino-3-methylbenz[a]anthraquinone (1) was established with decarboxylative alkylation, Pd(OAc)2-catalyzed cyclization, aromatization, and C−N coupling as the key steps. However, final assembly of marmycin A was hampered by the failure to obtain the carbohydrate fragment 2. Instead, a

  研究了天然产物mar霉素A的全合成。以脱羧烷基化，Pd（OAc）2催化的环化，芳构化和CN偶联为关键步骤，建立了关键片段8-氨基-3-甲基苯并[ a ]蒽醌（1）的快速合成策略。然而，由于无法获得碳水化合物片段2，mar霉素A的最终组装受阻。取而代之的是，使用InBr 3催化的C-和N以适度的产率制备了一个小霉素霉素A的去甲基类似物文库-糖基化反应。这些化合物的绝对构型通过将其光谱数据与with霉素A的光谱数据进行比较，并通过X射线分析得以证实。
• Efficient Synthesis of the Tetracyclic Aminoquinone Moiety of Marmycin A
  作者：Nathan Maugel、Barry B. Snider

  DOI：10.1021/ol9020496

  日期：2009.11.5

  An efficient four-step route to the tetracyclic aminoquinone moiety of marmycin A that proceeds in 41% overall yield from 5-nitronaphthoquinone and 5-methyl-1-vinylcyclohexene will facilitate preparation of marmycin A analogues for biological evaluation. The Diels-Alder reaction gave exclusively the desired adduct that is favored by steric considerations rather than the regioisomeric adduct that is favored by electronic considerations.