6-甲基-1,4-萘醌 | 605-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 6-甲基-1,4-萘醌
• 英文名称: 6-methyl-1,4-naphthoquinone
• 英文别名: 6-methylnaphthalene-1,4-dione
• CAS: 605-93-6
• 化学式: C₁₁H₈O₂
• mdl: MFCD04039611
• 分子量: 172.183
• InChiKey: OPKFWRVRCVCMJH-UHFFFAOYSA-N

物化性质

• 熔点：
  83-85°C
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  2-8°C，保存时建议使用惰性气体。

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  6-(溴甲基)-1,4-萘醌	6-(bromomethyl)-1,4-naphthoquinone	81402-03-1	C11H7BrO2	251.079
  ——	6-(hydroxymethyl)-1,4-naphthoquinone	81402-06-4	C11H8O3	188.183
  ——	6-Ethoxymethyl-[1,4]naphthoquinone	81402-11-1	C13H12O3	216.236
  ——	6-acetoxymethyl-1,4-naphthoquinone	81402-05-3	C13H10O4	230.22
  ——	6-(hydroxymethyl)-1,4-naphthoquinone N-methylcarbamate	81402-13-3	C13H11NO4	245.235
  ——	6-{[(methanesulfonyl)oxy]methyl}-1,4-naphthoquinone	81402-08-6	C12H10O5S	266.274
  ——	2-Brom-6-methyl-1,4-naphthochinon	87170-64-7	C11H7BrO2	251.079
  2-溴-7-甲基-1,4-萘醌	2-bromo-7-methyl-1,4-naphthoquinone	87170-65-8	C11H7BrO2	251.079
  ——	2-hydroxy-6-methylnaphthoquinone	58472-21-2	C11H8O3	188.183
  ——	6-(hydroxymethyl)-1,4-naphthoquinone N-(chloroethyl)carbamate	81402-15-5	C14H12ClNO4	293.707

反应信息

• 作为反应物：
  描述：

  6-甲基-1,4-萘醌 在 吡啶 、 氯化亚砜 、 氨基甲酸甲酯 作用下， 以 苯 为溶剂， 反应 9.0h， 以73%的产率得到6-Methylbenzo[f][2,1,3]benzothiadiazole-4,9-dione
  参考文献：
  名称：

  Use of Thiazyl Chlorides, Alkyl Carbamates, and Thionyl Chloride To Fuse 1,2,5-Thiadiazoles to Quinones and To Oxidize, Chlorinate, and Aminate Them

  摘要：

  Thiazyl chlorides in a simple one-step procedure fuse 1,2,5-thiadiazole rings to quinones. So do alkyl carbamates mixed with excess thionyl chloride and pyridine. Evidence is put forward to support the hypothesis that NSCl or a related thiazyl derivative is the reactive species that brings about the transformations. Selenoyl chloride mixed with an alkyl carbamate, pyridine, and quinones similarly gives 1,2,5-selenodiazoloquinones. Thionyl chloride in pyridine chlorinates quinones and oxidizes hydroquinones. 2,3-Dichloro-1,4-quinones with S4N4 or. with alkyl N-sulfinylcarbamates give 1,2,5-thiadiazoloquinones. Quinones and their 2 3-dichloro derivatives with TsNSO in pyridine give betaine derivatives of 2,3-diaminoquinones, which pyrrolidine converts into 2-amino-3(tosylamino)quinones. A unified set of mechanisms is presented that accounts for these transformations.

  DOI：

  10.1021/jo00110a036
• 作为产物：
  描述：

  6-methyl-5,8,9,10-tetrahydro-1,4-naphtoquinone 在 四氯苯醌 作用下， 以 苯 为溶剂， 反应 30.0h， 以45%的产率得到6-甲基-1,4-萘醌
  参考文献：
  名称：

  来自白花蛇舌草的蒽醌

  摘要：

  摘要 从白花蛇舌草中分离得到一种新的蒽醌，即2,3-二甲氧基-6-甲基蒽醌。

  DOI：

  10.1016/s0031-9422(00)81192-9

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。
• 6-Substituted 1,4-naphthoquinone oxime derivatives (I): synthesis and evaluation of their cytotoxic activity
  作者：Guang Huang、Hui-ran Zhao、Wen Zhou、Jin-yun Dong、Qi-jing Zhang、Qing-qing Meng、Bao-quan Zhu、Shao-shun Li

  DOI：10.1007/s00706-016-1899-z

  日期：2017.6

  4-naphthoquinone oxime derivatives were synthesized and evaluated for their in vitro cytotoxicity against four cancer cell lines and one normal cell line. Some compounds exhibited moderate to good cytotoxicity towards cancer cells and meanwhile all the synthesized compounds displayed no apparent cytotoxic activity against normal cells (IC50 > 100 μM). Among these oxime derivatives, three compounds showed more

  摘要合成了一系列6-取代的1,4-萘醌肟衍生物，并评估了它们对四种癌细胞系和一种正常细胞系的体外细胞毒性。一些化合物对癌细胞表现出中度到良好的细胞毒性，同时所有合成的化合物对正常细胞均没有表现出明显的细胞毒性活性（IC 50  > 100μM）。在这些肟衍生物中，三种化合物对人结肠癌细胞系（HCT-15）的杀伤力比阿霉素和5-氟尿嘧啶强，IC 50值分别为2.52、1.96和2.27μM。此外，结构-活性关系研究表明，这些肟衍生物的细胞毒性作用不仅在很大程度上取决于烷基链R 1的大小。，但在支链的取代基R 2上，表明这些化合物的强细胞毒性归因于其适当的亲脂性。总的来说，这项研究可以提供设计和合成6-取代的1,4-萘醌肟肟衍生物作为潜在抗癌药的可用策略。 图形概要
• Chlorination of Quinonoid Compounds Using Dichlorine Monoxide
  作者：Prakash C. Thapliyal、K. P. Singh、Rajinder N. Khanna

  DOI：10.1080/00397919408011701

  日期：1994.4

  Abstract Dichlorine monoxide is a selective reagent for the monochlorination at the active quinonoid position in benzoquinones and naphthoquinones.

  摘要 一氧化二氯是苯醌类和萘醌类中活性醌类位置单氯化的选择性试剂。
• Dichlororuthenium(IV) Complex ofmeso-Tetrakis(2,6-dichlorophenyl)porphyrin: Active and Robust Catalyst for Highly Selective Oxidation of Arenes, Unsaturated Steroids, and Electron-Deficient Alkenes by Using 2,6-DichloropyridineN-Oxide
  作者：Jun-Long Zhang、Chi-Ming Che

  DOI：10.1002/chem.200401008

  日期：2005.6.20

  under acid-free conditions, a wide variety of hydrocarbons including 1) cycloalkenes, conjugated enynes, electron-deficient alkenes (to afford epoxides), 2) arenes (to afford quinones), and 3) Delta5-unsaturated steroids, Delta4-3-ketosteroids, and estratetraene derivatives (to afford epoxide/ketone derivatives of steroids) in up to 99 % product yield within several hours with up to 100 % substrate conversion

  由[Ru（VI）（2,6-Cl2tpp）O2]与Me3SiCl的反应以90％的收率制备的[Ru（IV）（2,6-Cl2tpp）Cl2]是通过X射线晶体学表征的结构明显优于[Ru（IV）（tmp）Cl2]，[Ru（IV）（ttp）Cl2]和[Ru（II）（por）（CO）]（por = 2,6-Cl2tpp，F20-tpp ，F28-tpp）作为烯烃与2,6-Cl2pyNO（2,6-Cl2tpp = meso-tetrakis（2,6-dichlorophenyl）porphyrinato dianion; tmp = meso-tetramesitylporphyrinato dianion; ttp = meso-tetrakis（对甲苯基）卟啉二价阴离子; F20-tpp =间四（五氟苯基）卟啉二价阴离子; F28-tpp = 2,3,7,8,12,13,17,18-八氟-5,10,15
• Chromium(VI) oxide-catalyzed oxidation of arenes with periodic acid
  作者：Shigekazu Yamazaki

  DOI：10.1016/s0040-4039(01)00432-4

  日期：2001.5

  Chromium(VI) oxide was found to catalyze the oxidation of arenes such as naphthalenes and anthrathene to the corresponding quinones with periodic acid as the terminal oxidant in acetonitrile. 2-Methylnaphthalene was oxidized smoothly to 2-methyl-1,4-naphthoquinone (vitamin K3) by the catalytic system in high yield and regioselectivity.

  发现氧化铬（VI）以高碘酸为乙腈中的末端氧化剂催化芳烃（如萘和蒽）氧化为相应的醌。通过催化体系将2-甲基萘平稳地氧化成2-甲基-1,4-萘醌（维生素K 3），具有高产率和区域选择性。