2-Neopentyl-1,4-naphthoquinone | 142389-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Neopentyl-1,4-naphthoquinone
• 英文别名: 2-(2,2-Dimethylpropyl)naphthalene-1,4-dione
• CAS: 142389-14-8
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: UHRJQHGDUJWNAW-UHFFFAOYSA-N

物化性质

• 沸点：
  346.4±42.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Neopentyl-1,4-naphthoquinone 在 双氧水 、 sodium carbonate 、 硫酸 作用下， 生成 3-(2,2-dimethylpropyl)-4-hydroxynaphthalene-1,2-dione
  参考文献：
  名称：

  Design, Synthesis, and Biological Testing of Novel Naphthoquinones as Substrate-Based Inhibitors of the Quinol/Fumarate Reductase from Wolinella succinogenes

  摘要：

  Novel naphthoquinones were designed, synthesized, and tested as substrate-based inhibitors against the membrane-embedded protein quinol/fumarate reductase (QFR) from Wolinella succinogenes, a target closely related to QFRs from the human pathogens Helicobacter pylori and Campylobacter jejuni. For a better understanding of the hitherto structurally unexplored substrate binding pocket, a structure activity relationship (SAR) study was carried out. Analogues of lawsone (2-hydroxy-1,4-naphthoquinone 3a) were synthesized that vary in length and size of the alkyl side chains (3b-k). A combined study on the prototropic tautomerism of 2-hydroxy-1,4-naphthoquinones series indicated that the 1,4-tautomer is the more stable and biologically relevant isomer and that the presence of the hydroxyl group is crucial for inhibition. Furthermore, 2-bromine-1,4-naphthoquinone (4a-c) and 2-methoxy-1,4-naphthoquinone (5a-b) series were also discovered as novel and potent inhibitors. Compounds 4a and 4b showed IC50 values in low micromolar range in the primary assay and no activity in the counter DT-diaphorase assay.

  DOI：

  10.1021/jm400978u
• 作为产物：
  描述：

  3,3-二甲基-1-丁酸 、 1,4-萘醌 在 ammonium peroxydisulfate 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 生成 2-Neopentyl-1,4-naphthoquinone
  参考文献：
  名称：

  Design, Synthesis, and Biological Testing of Novel Naphthoquinones as Substrate-Based Inhibitors of the Quinol/Fumarate Reductase from Wolinella succinogenes

  摘要：

  Novel naphthoquinones were designed, synthesized, and tested as substrate-based inhibitors against the membrane-embedded protein quinol/fumarate reductase (QFR) from Wolinella succinogenes, a target closely related to QFRs from the human pathogens Helicobacter pylori and Campylobacter jejuni. For a better understanding of the hitherto structurally unexplored substrate binding pocket, a structure activity relationship (SAR) study was carried out. Analogues of lawsone (2-hydroxy-1,4-naphthoquinone 3a) were synthesized that vary in length and size of the alkyl side chains (3b-k). A combined study on the prototropic tautomerism of 2-hydroxy-1,4-naphthoquinones series indicated that the 1,4-tautomer is the more stable and biologically relevant isomer and that the presence of the hydroxyl group is crucial for inhibition. Furthermore, 2-bromine-1,4-naphthoquinone (4a-c) and 2-methoxy-1,4-naphthoquinone (5a-b) series were also discovered as novel and potent inhibitors. Compounds 4a and 4b showed IC50 values in low micromolar range in the primary assay and no activity in the counter DT-diaphorase assay.

  DOI：

  10.1021/jm400978u

文献信息

• A New Selective Method for the Homolytic Alkylation and Carboxylation of Quinones by Monoesters of Oxalic Acid
  作者：Fausta Coppa、Francesca Fontana、Edoardo Lazzarini、Francesco Minisci

  DOI：10.1246/cl.1992.1299

  日期：1992.7

  Alkyl and alkoxycarbonyl radicals were generated by oxidative decarboxylation of oxalic acid monoesters by persulfate; they were then utilized for the selective substitution of quinones.

  草酸单酯被过硫酸盐氧化脱羧生成烷基和烷氧羰基；然后将它们用于醌的选择性取代。
• Synthesis of 2-Alkyl-1,4-naphthoquinones by Alkylboration
  作者：Bernd Peter Ernst、Hartmut Laatsch

  DOI：10.1055/s-1992-26136

  日期：——

  By reaction of 1,4-naphthoquinone (1) and trialkylboranes in the presence of oxygen and oxidative work-up, sterically hindered 2-alkyl-1,4-naphthoquinones and, on addition of magnesium bromide, 2,3-bisalkyl-1,4-naphthoquinones are obtained.

  1,4-萘醌（1）和三烷基硼烷在氧气存在下发生反应并进行氧化加工，可得到立体受阻的 2-烷基-1,4-萘醌，加入溴化镁后可得到 2,3-双烷基-1,4-萘醌。
• Laatsch, Hartmut; Ernst, Bernd Peter, Liebigs Annalen der Chemie, 1992, # 12, p. 1245 - 1250
  作者：Laatsch, Hartmut、Ernst, Bernd Peter

  DOI：——

  日期：——