1,2,3,4-tetrahydro-1,5,12-trihydroxynaphthacene-6,11-dione | 20494-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 1,2,3,4-tetrahydro-1,5,12-trihydroxynaphthacene-6,11-dione
• 英文别名: 6,7,11-trihydroxy-7,8,9,10-tetrahydronaphthacene-5,12-dione；6,7,11-trihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione；6,7,11-Trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione
• CAS: 20494-73-9
• 化学式: C₁₈H₁₄O₅
• 分子量: 310.306
• InChiKey: NVNRWHHTJDJRHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,8-二甲氧基-1-四氢萘酮 在 sodium tetrahydroborate 、 lithium tert-butoxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 生成 1,2,3,4-tetrahydro-1,5,12-trihydroxynaphthacene-6,11-dione
  参考文献：
  名称：

  Direct Access to 1,4-Dihydroxyanthraquinones:  The Hauser Annulation Reexamined with p-Quinones

  摘要：

  3-Phenylsulfanylphthalides (e.g. 8a) readily react with p-benzoquinones in the presence of (LiOBu)-Bu-t in THF to furnish 1,4-dihydroxyanthraquinones in good yields and one-pot operations.

  DOI：

  10.1021/jo062271j

文献信息

• Chemistry of quinones. Part 7. Synthesis of anthracyclinone analogues via Diels–Alder reactions of 1,4-anthraquinones
  作者：Dharmendra N. Gupta、Philip Hodge、Naeem Khan

  DOI：10.1039/p19810000689

  日期：——

  Diels–Alder adducts were formed by reaction of 1,4-anthraquinone with buta-1,3-diene, with 1-acetoxy-, 1-methyl-, 2-methyl-, and 2,3-dimethyl-buta-1,3-diene, and with cyclohexa-1,3-diene. Adducts were also prepared by reaction of 9-chloro-10-hydroxy-1,4-anthraquinone with buta-1,3-diene and with 2-methylbuta-1,3-diene. Some of the linear tetracyclic adducts were transformed to 1,2,3,4-tetrahydro-1

  Diels–Alder加合物是由1，4-蒽醌与1,3-二丁烯与1-乙酰氧基，1-甲基，2-甲基和2,3-二甲基-buta-1反应形成的， 3-二烯和环己-1,3-二烯。还可以通过使9-氯-10-羟基-1,4-蒽醌与buta-1,3-二烯和2-甲基buta-1,3-二烯反应来制备加合物。一些线性四环加合物被转化为1,2,3,4-四氢-1,5,12-三羟基萘-6,11-醌（21）和2-乙酰基1,2,3,4-四氢- 2,5,12-三羟基萘-6,11-醌（7）。后者已被其他工人转换为4-脱甲氧基柔红霉素（48）和4-脱甲氧基柔红霉素（8）。
• Carretero, Juan Carlos; Cuevas, Juan Carlos; Echavarren, Antonio, Journal of Chemical Research, Miniprint, 1984, # 1, p. 147 - 194
  作者：Carretero, Juan Carlos、Cuevas, Juan Carlos、Echavarren, Antonio、Prados, Pilar、Farina, Francisco

  DOI：——

  日期：——
• Daunomycinone analogues via the Diels-Alder reaction. Synthesis and chemistry of some 6,11-dihydroxy-5,12-naphthacenediones
  作者：William W. Lee、Abelardo P. Martinez、Thomas H. Smith、David W. Henry

  DOI：10.1021/jo00875a018

  日期：1976.6
• Direct Access to 1,4-Dihydroxyanthraquinones:  The Hauser Annulation Reexamined with <i>p</i>-Quinones
  作者：Dipakranjan Mal、Sutapa Ray、Indrajeet Sharma

  DOI：10.1021/jo062271j

  日期：2007.6.1

  3-Phenylsulfanylphthalides (e.g. 8a) readily react with p-benzoquinones in the presence of (LiOBu)-Bu-t in THF to furnish 1,4-dihydroxyanthraquinones in good yields and one-pot operations.