4,8-Dihydroxy-3-methyl-3,4-dihydro-2H-naphthalen-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 4,8-Dihydroxy-3-methyl-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: 4,8-dihydroxy-3-methyl-3,4-dihydro-2H-naphthalen-1-one
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: YUPNHTWYVBHLMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,8-Dihydroxy-3-methyl-3,4-dihydro-2H-naphthalen-1-one 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到2,3-二氢-5-羟基-2-甲基-1,4-萘二酮
  参考文献：
  名称：

  Mechanism of antifeedant activity of plumbagin, a compound concerning the chemical defense in carnivorous plant

  摘要：

  Dionaea muscipula Ellis accumulates a large amount of plumbagin (1), which operates as an antifeedant against predators. Content of I reached 0.5% weight of the fresh trap lobes. It was found that other carnivorous plants also accumulated similar naphthoquinone-type strong antifeedant. Thus, naphthoquinone analogs are widely used as an antifeedant among the carnivorous plants. By using several analogs of 1, we clarified that both the high volatility and high redox potential of I are important for its strong antifeedant activity. It was known that plumbagin stimulates the mitochondrial electron transport system as a result of intercepting electrons. These results suggested that the Droseraceae family possesses a universal defensive mechanism against predators, that is, accumulation of volatile naphthoquinone with high redox potential as defensive substance. Thus, it is estimated that highly volatile naphthoquinone of moderately high redox potential would be used as an antifeedant of weak toxicity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.094
• 作为产物：
  描述：

  兰雪醌 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以55%的产率得到4,8-Dihydroxy-3-methyl-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Mechanism of antifeedant activity of plumbagin, a compound concerning the chemical defense in carnivorous plant

  摘要：

  Dionaea muscipula Ellis accumulates a large amount of plumbagin (1), which operates as an antifeedant against predators. Content of I reached 0.5% weight of the fresh trap lobes. It was found that other carnivorous plants also accumulated similar naphthoquinone-type strong antifeedant. Thus, naphthoquinone analogs are widely used as an antifeedant among the carnivorous plants. By using several analogs of 1, we clarified that both the high volatility and high redox potential of I are important for its strong antifeedant activity. It was known that plumbagin stimulates the mitochondrial electron transport system as a result of intercepting electrons. These results suggested that the Droseraceae family possesses a universal defensive mechanism against predators, that is, accumulation of volatile naphthoquinone with high redox potential as defensive substance. Thus, it is estimated that highly volatile naphthoquinone of moderately high redox potential would be used as an antifeedant of weak toxicity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.094

文献信息

• [EN] NAPHTHOQUINONE COMPOUND AND NUCLEAR FACTOR KAPPA-B (NF-κB) INHIBITOR COMPRISING SAME AS ACTIVE INGREDIENT<br/>[FR] COMPOSÉ DE NAPHTOQUINONE ET INHIBITEUR DE FACTEUR NUCLÉAIRE KAPPA-B (NF-κB) COMPRENANT CELUI-CI EN TANT QUE SUBSTANCE ACTIVE<br/>[JA] ナフトキノン化合物及び該化合物を有効成分とする核内因子カッパＢ（ＮＦ－κＢ）阻害剤
  申请人：POLA PHARMA INC

  公开号：WO2017099210A1

  公开（公告）日：2017-06-15

  本発明は、新規の核内因子κＢ（ＮＦ－ｋＢ）阻害剤を提供することを課題とする。　下記一般式（１）で表されるナフトキノン化合物又は薬学的に許容されるその塩を有効成分とする、ＮＦ－κＢ阻害剤。 （式中、Ｒ1及びＲ2は、同一又は異なって、水素原子、ヒドロキシ基、２－メチル－５－ヒドロキシ－１，４－ナフトキノン基、カルボニル基を有していても良いアルキル基、アルケニル基、及び水酸基を有していても良いアルキル基から選ばれる基を示し、Ｒ3は、ヒドロキシ基又は炭素数１～４のアルキル基を示し、Ｒ4は、ヒドロキシ基又はオキソ基を示し、破線部分は、単結合又は二重結合を示す。）
• Mechanism of antifeedant activity of plumbagin, a compound concerning the chemical defense in carnivorous plant
  作者：Takashi Tokunaga、Noboru Takada、Minoru Ueda

  DOI：10.1016/j.tetlet.2004.07.094

  日期：2004.9

  Dionaea muscipula Ellis accumulates a large amount of plumbagin (1), which operates as an antifeedant against predators. Content of I reached 0.5% weight of the fresh trap lobes. It was found that other carnivorous plants also accumulated similar naphthoquinone-type strong antifeedant. Thus, naphthoquinone analogs are widely used as an antifeedant among the carnivorous plants. By using several analogs of 1, we clarified that both the high volatility and high redox potential of I are important for its strong antifeedant activity. It was known that plumbagin stimulates the mitochondrial electron transport system as a result of intercepting electrons. These results suggested that the Droseraceae family possesses a universal defensive mechanism against predators, that is, accumulation of volatile naphthoquinone with high redox potential as defensive substance. Thus, it is estimated that highly volatile naphthoquinone of moderately high redox potential would be used as an antifeedant of weak toxicity. (C) 2004 Elsevier Ltd. All rights reserved.