2,3-二氢-5-羟基-2-甲基-1,4-萘二酮 | 74413-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2,3-二氢-5-羟基-2-甲基-1,4-萘二酮
• 英文名称: 2,3-dihydro-5-hydroxy-2-methyl-1,4-naphthalenedione
• 英文别名: plumbagin；2,3-dihydroplumbagin；5-hydroxy-2-methyl-2,3-dihydro-[1,4]naphthoquinone；5-Hydroxy-2-methyl-2,3-dihydro-[1,4]naphthochinon；(+/-)-5-Hydroxy-2-methyl-2,3-dihydro-naphthochinon-(1,4)；β-Dihydroplumbagin；(S)-2,3-Dihydro-5-hydroxy-2-methyl-1,4-naphthoquinone；5-hydroxy-2-methyl-2,3-dihydronaphthalene-1,4-dione
• CAS: 74413-19-7；79516-55-5
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: ALPCEXCHMFUSAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-二氢-5-羟基-2-甲基-1,4-萘二酮 、 alkaline earth salt of/the/ methylsulfuric acid 生成 2-methyl-1,4,5-naphthalenetriol
  参考文献：
  名称：

  Madinaveitia; Olay, Anales de la Real Sociedad Espanola de Fisica y Quimica, 1933, vol. 31, p. 134,136

  摘要：

  DOI：
• 作为产物：
  描述：

  兰雪醌 在 sodium dithionite 作用下， 以 乙醚 为溶剂， 生成 2,3-二氢-5-羟基-2-甲基-1,4-萘二酮
  参考文献：
  名称：

  Zeylanone和Isozeylanone，两种来自Plumbago Zeylanica的新颖醌

  摘要：

  业已证明，Zeylanone和isozeylanone是lumbagin的新型二聚体（2-甲基-5-羟基-1,4-萘醌）。推测它们可能在体内由李白蛋白（1）及其对苯二酚（3）形成（方案1）。已经讨论了苯诱导的吡喃酮芳族质子的溶剂转移。

  DOI：

  10.1016/0040-4020(79)88008-4

文献信息

• 275. Naturally occurring quinones. A new synthesis of plumbagin and a note on the structure of β-hydroplumbagin
  作者：R. H. Thomson

  DOI：10.1039/jr9510001237

  日期：——
• 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.
• BINDER, RONALD G.;BENSON, MABRY E.;FLATH, ROBERT A., PHYTOCHEMISTRY, 28,(1989) N0, C. 2799-2801
  作者：BINDER, RONALD G.、BENSON, MABRY E.、FLATH, ROBERT A.

  DOI：——

  日期：——
• Zeylanone and Isozeylanone, two novel quinones from Plumbago Zeylanica
  作者：Akella V.B. Sankaram、Adapa Srinivasa Rao、James N. Shoolery

  DOI：10.1016/0040-4020(79)88008-4

  日期：1979.1

  Zeylanone and isozeylanone have been shown to be novel dimers of plumbagin (2-methyl-5-hydroxy-1,4-naphthaquinone). A probable mode of their formation in vivo from plumbagin (1) and its hydroquinone (3) has been postulated (Scheme 1). Benzene induced solvent shifts of the aromatic protons of zeylanone have been discussed.

  业已证明，Zeylanone和isozeylanone是lumbagin的新型二聚体（2-甲基-5-羟基-1,4-萘醌）。推测它们可能在体内由李白蛋白（1）及其对苯二酚（3）形成（方案1）。已经讨论了苯诱导的吡喃酮芳族质子的溶剂转移。
• Madinaveitia; Olay, Anales de la Real Sociedad Espanola de Fisica y Quimica, 1933, vol. 31, p. 134,136
  作者：Madinaveitia、Olay

  DOI：——

  日期：——