3-hydroxy-5-methyl-1,4-naphthoquinone | 25132-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-hydroxy-5-methyl-1,4-naphthoquinone
• 英文别名: 2-hydroxy-8-methyl-[1,4]naphthoquinone；2-Hydroxy-8-methyl-[1,4]naphthochinon；3-hydroxy-5methyl-1,4-naphthoquinone；2-hydroxy-8-methylnaphthoquinone；3-Hydroxy-5-methyl-<1,4>naphthoquinone；3-Hydroxy-5-methyl-1,4-naphthochinon
• CAS: 25132-42-7
• 化学式: C₁₁H₈O₃
• 分子量: 188.183
• InChiKey: CUOBAGCJXFVVNG-UHFFFAOYSA-N

物化性质

• 熔点：
  175-176 °C(Solv: ligroine (8032-32-4))
• 沸点：
  379.6±42.0 °C(Predicted)
• 密度：
  1.406±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-hydroxy-5-methyl-1,4-naphthoquinone 在 偶氮二异丁腈 、 三正丁基氢锡 、 potassium carbonate 、 potassium hydroxide 作用下， 以 苯 为溶剂， 生成 2-OH-3-(2-methyl-octyl)-8-methyl-naphthoquinone
  参考文献：
  名称：

  Asymmetric syntheses of potential anti-malarial drugs designed from Fieser's 2-hydroxy-3-(2-methyloctyl)naphthalene-1,4-dione

  摘要：

  DOI：

  10.24820/ark.5550190.p011.206
• 作为产物：
  描述：

  2-甲氧基对苯二酚 在 sodium periodate 、 氧气 、 三乙胺 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 生成 3-hydroxy-5-methyl-1,4-naphthoquinone
  参考文献：
  名称：

  Asymmetric syntheses of potential anti-malarial drugs designed from Fieser's 2-hydroxy-3-(2-methyloctyl)naphthalene-1,4-dione

  摘要：

  DOI：

  10.24820/ark.5550190.p011.206

文献信息

• Synthesis and antiallergic activity of 2-hydroxy-3-nitro-1,4-naphthoquinones
  作者：Derek R. Buckle、Barrie C. C. Cantello、Harry Smith、Raymond J. Smith、Barbara A. Spicer

  DOI：10.1021/jm00218a014

  日期：1977.8

  have highest potency with alkyl substitution at both C-6 and C-7. The most potent compounds were 7c and 7e which produced a 50% inhibition in the rat PCA test at doses of about 10 micrometerM/kg following subcutaneous administration and showed activity after oral administration. Related 4-hydroxy-3-nitro-2(1H)-naphthalenones had no effect on rat PCA in doses up to 500 micrometerM/kg.

  新型2-羟基-3-硝基-1,4-萘醌的选择被证明是大鼠被动皮肤过敏反应（PCA）的有效抑制剂，并且在C-6和C-7处具有最高的烷基取代效力。最有效的化合物是7c和7e，它们在大鼠PCA测试中以约10微米M / kg的剂量在皮下给药后产生50％的抑制作用，并在口服后显示出活性。相关的4-羟基-3-硝基-2（1H）-萘烯酮对大鼠PCA的影响最大为500 microM / kg。
• 2-Hydroxy-3-nitro-1,4-naphthoquinones
  申请人：Beecham Group Limited

  公开号：US04014907A1

  公开（公告）日：1977-03-29

  Substituted naphthoquinones of the formula (I) and pharmaceutically acceptable salts thereof wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent alkyl, aryl, alkoxy, hydroxy, hydrogen or halogen or any two of the groups R.sub.1, R.sub.2, R.sub.3 and R.sub.4 taken together complete a carbocyclic ring, have useful anti-allergy activity in mammals.

  公式(I)的取代萘醌及其药用盐，其中R.sub.1、R.sub.2、R.sub.3和R.sub.4代表烷基、芳基、烷氧基、羟基、氢或卤素，或者R.sub.1、R.sub.2、R.sub.3和R.sub.4中的任意两个一起形成一个碳环，对哺乳动物具有有用的抗过敏活性。
• The chemistry of Quinones. I. Directive effects in the Substitution of Naphthoquinones
  作者：RG Cooke、H Dowd、W Segal

  DOI：10.1071/ch9530038

  日期：——

  The reaction of dimethylamine with 5-methoxy-1,4-naphthoquinone gives approximately equal amounts of the two possible substitution products and with 6-methyl-1,4-naphthoquinone followed by acid hydrolysis 2-hydroxy-6-methyl-l,4-naphtho-quinone is the principal product. Similar treatment of 5-methyl-1,4-naphthoquinone gives mostly 3-hydroxy-5-methyl-l,4-naphtlioquinone. The isomer, 2-hydroxy-5- methyl-1,4-naphthoquinone, has been prepared by another method. The product of Thiele-Winter addition of acetic anhydride to juglone is shown to be a mixture of the two possible isomers, but authentic 1,3,4,5-tetra-acetoxynaphthalene has been prepared from 3,5-dihydroxy-1,4-naphthoquinone. The reaction of acetic anhydride with plumbagin gives three compounds, the composition of the mixture depending on the time of contact. Juglone and plumbagin have been selectively brominated in the 6-position and certain other halogen derivatives of these quinones have been prepared. The preparation of 3-chloro-5-hydroxy-2-methyl-1,4-naphthoquinone provides a new route by which droserone may be obtained from plumbagin.

  二甲胺与 与 5-甲氧基-1,4-萘醌的反应会产生近似等量的两种可能的取代产物。 与 6-甲基-1,4-萘醌反应，然后进行酸水解，可生成 2-羟基-6-甲基-1,4-萘醌。 2-hydroxy-6-methyl-l,4-naphtho-quinone 是主要产物。 产物。对 5-甲基-1,4-萘醌进行类似处理后，主要产物为 3-羟基-5-甲基-l,4-萘醌。异构体 2-羟基-5-甲基-1,4-萘醌是主要产物。 甲基-1,4-萘醌的异构体。其产物为 乙酸酐与丁二酮的 Thiele-Winter 加成产物被证明是两种可能异构体的混合物。 但真正的 1，3，4，5-四乙酰氧基萘是由 3，5-二乙酰氧基萘制备的。 但真正的 1,3,4,5-四乙酰氧基萘是由 3,5-二羟基-1,4-萘醌制备的。乙酸酐与 反应生成三种化合物，混合物的成分取决于接触的时间。 取决于接触的时间。Juglone 和 plumbagin 在 6 位被选择性溴化。 6 位溴化，并制备出了这些醌类化合物的某些其他卤素衍生物。 醌的某些其他卤素衍生物。3-氯-5-羟基-2-甲基-1,4-萘醌的制备方法 提供了一条从 plumbagin 中获得 droserone 的新途径。
• 2-Hydroxy-3-nitro-1,4-naphthoquinones for the prophylaxis of certain
  申请人：Beecham Group Limited

  公开号：US04017639A1

  公开（公告）日：1977-04-12

  Substituted naphthoquinones of the formula (I) and pharmaceutically acceptable salts thereof wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent alkyl, aryl, alkoxy, hydroxy, hydrogen or halogen or any two of the groups R.sub.1, R.sub.2, R.sub.3 and R.sub.4 taken together complete a carbocyclic ring, have useful anti-allergy activity in mammals.

  公式（I）的取代萘醌及其药学上可接受的盐，其中R1、R2、R3和R4代表烷基、芳基、烷氧基、羟基、氢或卤素，或者R1、R2、R3和R4中的任意两个组合在一起形成一个碳环，具有哺乳动物中有用的抗过敏活性。
• Synthesis and efficiency of photolysis of methylated 2-dialkylamino- and 2-piperidino-1,4-naphthoquinones
  作者：V. V. Russkikh

  DOI：10.1007/bf00863084

  日期：1992.3

  2-Dialkylamino- and 2-piperidino-1,4-naphthoquinones with a methyl group in position 3 or 5(8) of the naphthoquinones were synthesized by reacting dimethyl- and diethylamines and piperidine with 2- and 5-methyl-1,4-naphthoquinones. The quantum yields of photoconversion of the synthesized compounds in benzene were determined. A 1.2- to 6.5-fold increase of the quantum yield over that of 2-dimethylamino-1,4-napthoquinone was established. A comparison of the quantum yields with the calculated charges on the reaction centers in the excited (T1) state showed that there is not a linear relationship between them.