trimethylnaphthazarin | 32741-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: trimethylnaphthazarin
• 英文别名: 2,3,6-trimethylnaphthazarin；5,8-dihydroxy-2,3,6-trimethylnaphthalene-1,4-dione
• CAS: 32741-24-5
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: OUCGHLVGAZCZKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  trimethylnaphthazarin 在 盐酸 、 manganese(IV) oxide 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.17h， 生成 2,3,7-trichloro-5,8-dihydroxy-2,3,6-trimethyl-1,2,3,4-tetrahydronaphthalene-1,4-dione
  参考文献：
  名称：

  Chlorination of 2,3,6-trialkyl-5,8-dihydroxy-1,4-naphthoquinones with HCl-MnO2 in acetic acid. effective transformation of 2,3,6-trialkyl-2,3,7-trichloro-1,2,3,4-tetrahydronaphthalene-1,4-diones into 7-chloro-2,3,6-trialkyl-5,8-dihydroxy-1,4-naphthoquinones

  摘要：

  Chlorination of 2,3,6-trialkyl-5,8-dihydroxy-1,4-naphthoquinones with HCl-MnO2 in acetic acid gave a mixture of 7-chloro-2,3,6-trialkyl-5,8-dihydroxy-1,4-naphthoquinones and 2,3,7-trichloro-2,3,6-trialkyl-1,2,3,4-tetrahydronaphthalene-1,4-diones, the latter being formed via addition of the second chlorine molecule to monochloro derivatives. The reduction of 2,3,7-trichloro-2,3,6-trialkyl-1,2,3,4-tetrahydronaphthalene-1,4-diones with sodium dithionite in alkaline medium resulted in the formation of 7-chloro-2,3,6-trialkyl-5,8-dihydroxy-1,4-naphthoquinones in high yield.

  DOI：

  10.1134/s1070428011070128
• 作为产物：
  描述：

  柠康酸酐 、 三甲基氢醌 在 三氯化铝 、 sodium chloride 作用下， 以83%的产率得到trimethylnaphthazarin
  参考文献：
  名称：

  萘甲素衍生物的化学。11. 三取代氢醌衍生物在萘并芴素的制备合成中的应用

  摘要：

  三甲基氢醌、3,5-二乙基-2-羟基氢醌和 3,5-二乙基-1,2,4-三甲氧基苯与二氯马来酸酐或柠康酸酐在 AlCl3-NaCl 熔体中的 Friedel-Crafts 酰化伴随 oC-脱烷基化为提供功能性取代的萘萨林。

  DOI：

  10.1023/b:rucb.0000011886.03785.bd

文献信息

• NMR studies of intramolecular proton exchange in alkylated naphthazarins
  作者：Gülnur A. Elöve、J. Herman Schauble

  DOI：10.1002/mrc.1260250303

  日期：1987.3

  Three groups of alkyl‐substituted naphthazarins were studied by 1H and 13C NMR in chloroform‐d at ambient temperature. Preliminary 1H NMR studies were carried out on selected members of each group at low temperatures (down to –120 °C) in dichloromethane‐d2 solution. Monoalkylnaphthazarins were found to exist predominantly as the 2‐alkyl tautomers (I) and the dimethylalkyl species as the 2,3‐dimethyl‐6‐alkyl

  在环境温度下，在氯仿-d 中通过 1H 和 13C NMR 研究了三组烷基取代的萘萨林。在低温（低至 –120 °C）下，在二氯甲烷-d2 溶液中对每组的选定成员进行了初步 1H NMR 研究。发现单烷基萘甲素主要以 2-烷基互变异构体 (I) 的形式存在，二甲基烷基以 2,3-二甲基-6-烷基互变异构体 (I) 的形式存在。然而，对称和非对称取代的 2,6- 和 2,7-二烷基萘并林表现出平均化学位移和耦合常数，表明两种最低能量 1,4-二酮互变异构体（I 和 II）之间的快速质子交换。13C NMR 位移用于计算不对称 2,6- 和 2,7-（甲基，烷基）萘并芴素的互变异构体群。
• Synthesis of water-soluble N-Acetyl-L-cysteine conjugates of naphtazarin (5,8-Dihydroxy-1,4-naphthoquinone) derivatives
  作者：Yu. E. Sabutskii、N. S. Polonik、V. A. Denisenko、P. S. Dmitrenok、S. G. Polonik

  DOI：10.1134/s1070428013080101

  日期：2013.8

  Base-catalytic condensation of N-acetyl-L-cysteine with substituted naphthazarins was first obtained a series of mono-, di-, tri- and tetra-substituted S-aminoacid naphthazarin conjugates bearing alkyl (hydroxy) groups. It was shown that three- and tetra-N-acetyl-L-cysteine naphthazarin derivatives are readily soluble in water.
• Chemistry of naphthazarin derivatives. 11. Trisubstituted hydroquinone derivatives in the preparative synthesis of naphthazarins
  作者：V. Ph. Anufriev、S. G. Polonik、N. D. Pokhilo、N. N. Balanyova

  DOI：10.1023/b:rucb.0000011886.03785.bd

  日期：2003.10

  5-diethyl-2-hydroxyhydroquinone, and 3,5-diethyl-1,2,4-trimethoxybenzene with dichloromaleic or citraconic anhydride in an AlCl3—NaCl melt is accompanied by o-C-dealkylation to afford functionally substituted naphthazarins.

  三甲基氢醌、3,5-二乙基-2-羟基氢醌和 3,5-二乙基-1,2,4-三甲氧基苯与二氯马来酸酐或柠康酸酐在 AlCl3-NaCl 熔体中的 Friedel-Crafts 酰化伴随 oC-脱烷基化为提供功能性取代的萘萨林。
• Chlorination of 2,3,6-trialkyl-5,8-dihydroxy-1,4-naphthoquinones with HCl-MnO2 in acetic acid. effective transformation of 2,3,6-trialkyl-2,3,7-trichloro-1,2,3,4-tetrahydronaphthalene-1,4-diones into 7-chloro-2,3,6-trialkyl-5,8-dihydroxy-1,4-naphthoquinones
  作者：N. S. Polonik、S. G. Polonik、V. A. Denisenko、O. P. Moiseenko、V. F. Anufriev

  DOI：10.1134/s1070428011070128

  日期：2011.7

  Chlorination of 2,3,6-trialkyl-5,8-dihydroxy-1,4-naphthoquinones with HCl-MnO2 in acetic acid gave a mixture of 7-chloro-2,3,6-trialkyl-5,8-dihydroxy-1,4-naphthoquinones and 2,3,7-trichloro-2,3,6-trialkyl-1,2,3,4-tetrahydronaphthalene-1,4-diones, the latter being formed via addition of the second chlorine molecule to monochloro derivatives. The reduction of 2,3,7-trichloro-2,3,6-trialkyl-1,2,3,4-tetrahydronaphthalene-1,4-diones with sodium dithionite in alkaline medium resulted in the formation of 7-chloro-2,3,6-trialkyl-5,8-dihydroxy-1,4-naphthoquinones in high yield.