5,8-dihydroxy-2,3-dimethyl-6-ethyl-1,4-naphthoquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,8-dihydroxy-2,3-dimethyl-6-ethyl-1,4-naphthoquinone
• 英文别名: 6-ethyl-5,8-dihydroxy-2,3-dimethyl-1,4-naphthoquinone；6-ethyl-2,3-dimethylnaphthazarin
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: MOHCMFYPJJDNGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  5,8-dihydroxy-2,3-dimethyl-6-ethyl-1,4-naphthoquinone 在 盐酸 、 manganese(IV) oxide 、 sodium dithionite 、 potassium hydroxide 作用下， 以 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 1.25h， 生成 7-chloro-6-ethyl-5,8-dihydroxy-2,3-dimethyl-1,4-dihydronaphthalene-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：

  2,3-二甲基马来酸酐 、 2-乙基-1,4-二甲氧基苯 在 aluminum (III) chloride 、 sodium chloride 作用下， 以40%的产率得到5,8-dihydroxy-2,3-dimethyl-6-ethyl-1,4-naphthoquinone
  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

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.
• 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.