1,6-dimethyl-2-(methylsulfanyl)pyrimidin-4(1H)-one | 54069-33-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,6-dimethyl-2-(methylsulfanyl)pyrimidin-4(1H)-one
• 英文别名: 1,6-dimethyl-2-methylsulfanyl-1H-pyrimidin-4-one；1,6-dimethyl-2-methylthio-4-pyrimidone；1,6-dimethyl-2-methylsulfanyl-1H-pyrimidin-4-one；1,6-Dimethyl-2-methylmercapto-1H-pyrimidin-4-on；1,6-dimethyl-2-(methylthio)-4(1H)-pyrimidinone；1,6-dimethyl-2-methylsulfanylpyrimidin-4-one
• CAS: 54069-33-9
• 化学式: C₇H₁₀N₂OS
• 分子量: 170.235
• InChiKey: HXLDWBVPJMGMOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  1,6-dimethyl-2-(methylsulfanyl)pyrimidin-4(1H)-one 在 盐酸 、 氢氧化钾 、 硫酸 、 硝酸 作用下， 生成 3-butyl-1,6-dimethyl-5-nitro-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Senda; Suzui, Chemical and pharmaceutical bulletin, 1958, vol. 6, p. 476,478

  摘要：

  DOI：
• 作为产物：
  描述：

  甲醇 、 6-甲基-4-羟基-2-甲硫基嘧啶 在 HY-Zeolite 作用下， 213.0 ℃ 、2.44 MPa 条件下， 反应 1.75h， 以90%的产率得到1,6-dimethyl-2-(methylsulfanyl)pyrimidin-4(1H)-one
  参考文献：
  名称：

  Regioselective N-Methylation of Methylthio-Substituted Pyrimidinones and 1,2,4-Triazinone with Methanol over H-Y Zeolite.

  摘要：

  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.

  DOI：

  10.1080/00397919708004083

文献信息

• Antithyroid Drugs and their Analogues Protect Against Peroxynitrite-Mediated Protein Tyrosine Nitration-A Mechanistic Study
  作者：Krishna P. Bhabak、Govindasamy Mugesh

  DOI：10.1002/chem.200902145

  日期：2010.1.25

  the presence of a thione or selone moiety is important for an efficient inhibition. Similarly, the replacement of NH moiety in MMI by N‐methyl or N‐m‐methoxybenzyl substituents dramatically reduces the antioxidant activity of the parent compound. Theoretical studies indicate that the substitution of NH moiety by NMe significantly increases the energy required for the oxidation of sulfur center by

  本文描述了一些常用的抗甲状腺药物及其类似物对过氧亚硝酸盐介导的蛋白质硝化作用的影响。通过蛋白质印迹分析研究了牛血清白蛋白（BSA）和细胞色素c中酪氨酸残基的硝化作用。这些研究表明，抗甲状腺药甲巯咪唑（MMI）6- n包含硫酮部分的-2-丙基-2-硫氧嘧啶（PTU）和6-甲基-2-硫氧嘧啶（MTU）显着降低BSA和细胞色素c的酪氨酸硝化作用。虽然MMI表现出良好的过氧亚硝酸盐（PN）清除活性，但硫尿嘧啶化合物PTU和MTU的效力略低于MMI。S-和Se-甲基化的化合物在酪氨酸的硝化中显示出弱的抑制作用，表明硫酮或selone部分的存在对于有效抑制很重要。类似地，替换N个在MMI H部分由Ñ甲基或ñ -米甲氧基苄基的取代基显着地降低了母体化合物的抗氧化活性。理论研究表明，N的替代NMe的H部分显着增加了PN氧化硫中心所需的能量。然而，在MMI的硒类似物中的这种取代增加了母体化合物的活性。
• Polyfunctional Derivatives of Isocytosine. Effect of Hydration on Prototropic Tautomerism of 2-(2-Hydroxyethyl)amino-6-methylpyrimidin-4(3H)-one
  作者：A. V. Erkin、V. I. Krutikov

  DOI：10.1007/s11176-005-0287-x

  日期：2005.4

  Hydration of 2-(2-hydroxyethyl)amino-6-methylpyrimidin-4(3 H )-one forms an equilibrium mixture of 4-oxo-3,4-dihydro and 4-hydroxy tautomers. The intermediate in mutual transitions of these tautomers has a zwitter ionic structure. The equilibrium shifts to the 4-oxo-3,4-dihydro form as the polarity of the medium decreases.

  2-（2-羟乙基）氨基-6-甲基嘧啶-4（ 3H ）-的水合 形成4-氧代-3,4-二氢和4-羟基互变异构体的平衡混合物。这些互变异构体相互过渡的中间体具有两性离子结构。随着介质极性的降低，平衡转变为4-氧代-3,4-二氢形式。
• THE BEHAVIOR OF 6-METHYL-2-THIOURACIL TOWARDS WITTIG-HORNER REAGENTS
  作者：El-Sayed M.A. Yakoup、Dalal B. Giurgius、L. S. Boulos

  DOI：10.1080/10426509908037009

  日期：1999.5.1

  6-Methyl-2-thiouracil (1) reacts with Wittig-Horner (2a-e) reagents to give the new products 3, 4, 6, 7 and 9 along with the alkylated derivatives 5, 8 and 10. When 1 was treated with 2e and/or 2f, the alkylated compound 10 is the sole reaction prduct. Possible reaction mechanism are considered and the structural assignments are based on compatible analytical and spectroscopic results.