1-methyl-2-methysulfanylpyrimidin-4(1H)-one | 6330-98-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-methyl-2-methysulfanylpyrimidin-4(1H)-one
• 英文别名: 1-methyl-2-methylthio-4(1H)pyrimidinone；2-methylthio-1-methylpyrimidin-4-one；1-methyl-2-methylthio-4-pyrimidone；N-1,S-Dimethyl-2-thiouracil；1,2-dimethyl-2-thiouracil；1-methyl-2-methylsulfanyl-1H-pyrimidin-4-one；1H-4-Pyrimidinone, 1-methyl-2-methylthio-；1-methyl-2-methylsulfanylpyrimidin-4-one
• CAS: 6330-98-9
• 化学式: C₆H₈N₂OS
• 分子量: 156.208
• InChiKey: UXFZQLMBACDHEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-2-methysulfanylpyrimidin-4(1H)-one 在 sodium hydroxide 、 水 作用下， 生成 1-甲基尿嘧啶
  参考文献：
  名称：

  Effect of the Structure of 1- and 3-Methylpyrimidin-4-ones on the Rate of Nucleophilic Substitution of the 2-Methylsylfanyl Group

  摘要：

  Rate constants for substitution of the 2-methylsulfanyl group in 1- and 3-methyl-2-methylsulfanylpyrimidin-4-ones and their 5-fluoro analogs were measured in the reaction with butylamine, alkaline hydrolysis, and methanolysis. The rate of substitution in 1-methyl isomers having a zwitterionic structure is greater by a factor of similar to2 than the rate of substitution in 3-methyl isomers with conjugated double bonds in the ring. The presence of a fluorine atom in position 5 accelerates nucleophilic substitution in 1-methyl isomers, while 5-fluoro-3-methyl-2-methylsulfanylpyrimidin-4-ones react at a lower rate than their 5-unsubstituted analogs. According to the NMR data, the reactions involve formation of a tetrahedral intermediate. Anchimeric effect of the methyl group on N-1 hampers attack by basic reagent on the C-6 atom.

  DOI：

  10.1023/b:rujo.0000034918.26019.44
• 作为产物：
  描述：

  2-硫脲嘧啶 、 硫酸二甲酯 生成 1-methyl-2-methysulfanylpyrimidin-4(1H)-one
  参考文献：
  名称：

  Sato, Eisuke; Machida, Minoru; Kanaoka, Yuichi, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 6, p. 1722 - 1729

  摘要：

  DOI：

文献信息

• Hayashi, Masahiro; Hisanaga, Yorisata; Yamauchi, Kiyoshi, Synthetic Communications, 1980, vol. 10, # 10, p. 791 - 798
  作者：Hayashi, Masahiro、Hisanaga, Yorisata、Yamauchi, Kiyoshi、Kinoshita, Masayoshi

  DOI：——

  日期：——
• Katritzky, Alan R.; Baykut, Gokhan; Rachwal, Stanislaw, Journal of the Chemical Society. Perkin transactions II, 1989, p. 1499 - 1506
  作者：Katritzky, Alan R.、Baykut, Gokhan、Rachwal, Stanislaw、Szafran, Miroslaw、Caster, Kenneth C.、Eyler, John

  DOI：——

  日期：——
• Brown et al., Journal of the Chemical Society, 1955, p. 211,216
  作者：Brown et al.

  DOI：——

  日期：——
• Kheifets; Kol'tsov; Khachaturov, Russian Journal of Organic Chemistry, 2000, vol. 36, # 9, p. 1373 - 1387
  作者：Kheifets、Kol'tsov、Khachaturov、Gindin

  DOI：——

  日期：——
• Regioselective N-Methylation of Methylthio-Substituted Pyrimidinones and 1,2,4-Triazinone with Methanol over H-Y Zeolite.
  作者：Majid M. Heravi、Hossian A. Oskooi、Morteza Mafi

  DOI：10.1080/00397919708004083

  日期：1997.5

  Liquid - phase methylation of 2-methylthio-4-pyrimidone (4), 6-methyl-2-methylthio-4-pyrimidone (5) and 6-methyl-3-methylthio-1,2,4-triazine-5-one (6) with MeOH over HY-Zeolite selectively gave 1-methyl-2-methylthio-4-pyrimidone (7),1,6-dimethyl-2-methylthio-4-pyrimidone (9) and 2,6-dimethyl-3-methylthio-1,24-triazine-5-one (11), respectively. Methyl iodide or dimethyl sulfate have been used as methylating agents for pyrimidines(1-3) and 1,2,4-triazines(4,5). Alkylation of 2-thiouracil (1) and 6-methyl-2-thiouracil (2) with methyl iodide under basic conditions is known to lead.