5,7-Dihydroxy-2-methoxy-1,4-naphthoquinone | 24308-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,7-Dihydroxy-2-methoxy-1,4-naphthoquinone
• 英文别名: 5,7-Dihydroxy-2-methoxynaphthalene-1,4-dione；5,7-dihydroxy-2-methoxynaphthalene-1,4-dione
• CAS: 24308-01-8
• 化学式: C₁₁H₈O₅
• 分子量: 220.182
• InChiKey: RAFCFIBVJBDWPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7-Dihydroxy-2-methoxy-1,4-naphthoquinone 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 silica gel supported sodium hydrogen sulfate 、 C₄H₁₂N⁽¹⁺⁾*C₂H₆I^(1-) 、 三溴化硼 、 potassium carbonate 、 caesium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 41.5h， 生成 δ-rubromycin
  参考文献：
  名称：

  Total Synthesis of (±)-δ-Rubromycin

  摘要：

  Transition-metal-catalyzed spiroketalization cyclization has been performed successfully and has led to the first total synthesis of (+/-)-delta-rubromycin with a longest linear sequence of 18 steps from commercially available guaiacol in a 2.7% overall yield.

  DOI：

  10.1021/ol400864f
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以100%的产率得到5,7-Dihydroxy-2-methoxy-1,4-naphthoquinone
  参考文献：
  名称：

  Total Synthesis of (±)-δ-Rubromycin

  摘要：

  Transition-metal-catalyzed spiroketalization cyclization has been performed successfully and has led to the first total synthesis of (+/-)-delta-rubromycin with a longest linear sequence of 18 steps from commercially available guaiacol in a 2.7% overall yield.

  DOI：

  10.1021/ol400864f

文献信息

• A New Method for Thiomethylation of Hydroxy-1,4-naphthoquinones with N-Acetyl-l-cysteine; First Synthesis of Fibrostatins B, C, and D
  作者：Sergey Polonik、Yuri Sabutskii、Vladimir Denisenko、Pavel Dmitrenok

  DOI：10.1055/s-0034-1378522

  日期：——

  4-dioxo-1,4-dihydronaphthalen-2-yl)methyl]-l-cysteine conjugates were obtained in good yields by acid-catalyzed condensation of substituted 2-hydroxy-1,4-naphthoquinones with N-acetyl-l-cysteine and paraform­aldehyde. Based on this reaction, a first synthesis of fibrostatins B, C, and D was developed. A series of N-acetyl-S-[(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl]-l-cysteine conjugates were

  摘要 通过酸催化取代基的缩合反应，可以得到高收率的一系列N-乙酰基-S -[（3-羟基-1,4-二氧杂-1,4-二氢萘-2-基）甲基] -1-半胱氨酸结合物。 2-羟基-1，4-萘醌与N-乙酰基-1-半胱氨酸和多聚甲醛。基于该反应，开发了纤维抑素B，C和D的第一合成。 通过酸催化取代基的缩合反应，可以得到高收率的一系列N-乙酰基-S -[（3-羟基-1,4-二氧杂-1,4-二氢萘-2-基）甲基] -1-半胱氨酸结合物。 2-羟基-1，4-萘醌与N-乙酰基-1-半胱氨酸和多聚甲醛。基于该反应，开发了纤维抑素B，C和D的第一合成。
• Synthesis of juglone derivatives
  作者：H. Singh、T.L. Folk、P.J. Scheuer

  DOI：10.1016/0040-4020(69)80052-9

  日期：——

  A number of hydroxyjuglones were prepared by the Thiele-Winter reaction onjuglone derivatives and by hydroxylation with ethanol-hydrochloric acid: 2-hydroxy, 3-hydroxy, 2,7-dihydroxy, 3,7-di-hydroxy, 6-acetyl-2-hydroxy, and 6-acetyl-3-hydroxyjuglone. By reductive acetylation of hydroxyjuglones, followed by Fries rearrangement and oxidative hydrolysis several acetyljuglones, and from them ethyljuglones

  通过Thiele-Winter反应onjuglone衍生物并用乙醇-盐酸进行羟基化反应，制得了许多羟基juglones：2-羟基，3-羟基，2,7-二羟基，3,7-二羟基，6-乙酰基-2 -羟基和6-乙酰基-3-羟基juglone。通过对羟基juglones进行还原性乙酰化，然后进行弗里斯重排和氧化水解，从而合成了几个乙酰juglones，并通过硼氢化钠还原从中合成了乙基juglones：3-乙酰基-2-羟基，6-乙酰基-2,3-二羟基，6-乙酰基- 2,7-二羟基和6-乙酰基-2,3,7-三羟基胡胶。先前已从海胆棘中分离出几种新合成的化合物。
• Development of approaches to fibrostatin F, N-acetyl-L-cysteinyl-containing 1,4-naphthoquinone metabolite of Streptomyces catenulae
  作者：Yu. E. Sabutskii、V. A. Denisenko、P. S. Dmitrenok、S. G. Polonik

  DOI：10.1007/s11172-016-1372-5

  日期：2016.3

  the synthesis of microbial metabolite Streptomyces catenulae fibrostatin F through the AcOH-catalyzed condensation of 5-hydroxy-3-hydroxymethyl-2,7-dimethoxy1,4-naphthoquinone and its related 3-chloromethyl, 3-acetoxymethyl, and 3-methoxymethyl derivatives with N-acetyl-L-cysteine and paraformaldehyde in 1,4-dioxane was studied. In these conditions, all naphthoquinones gave N-acetyl-S-[(8-hydroxy-3,6-dimethoxy-1

  通过 AcOH 催化 5-羟基-3-羟甲基-2,7-二甲氧基1,4-萘醌及其相关 3-氯甲基、3-乙酰氧基甲基和 3- 缩合合成微生物代谢物链霉菌纤维抑制素 F 的可能性研究了在 1,4-二恶烷中具有 N-乙酰基-L-半胱氨酸和多聚甲醛的甲氧基甲基衍生物。在这些条件下，所有的萘醌都将 N-乙酰基-S-[(8-羟基-3,6-二甲氧基-1,4-二氧萘-2-基)甲基]-L-半胱氨酸异构体转化为天然纤维抑制素 C。
• Total Synthesis of (±)-δ-Rubromycin
  作者：Wenjing Wang、Jijun Xue、Tian Tian、Jie Zhang、Liping Wei、Jidong Shao、Zhixiang Xie、Ying Li

  DOI：10.1021/ol400864f

  日期：2013.5.17

  Transition-metal-catalyzed spiroketalization cyclization has been performed successfully and has led to the first total synthesis of (+/-)-delta-rubromycin with a longest linear sequence of 18 steps from commercially available guaiacol in a 2.7% overall yield.