6-甲基-2-(丙硫基)嘧啶-4-醇 | 62459-04-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 6-甲基-2-(丙硫基)嘧啶-4-醇
• 英文名称: 6-methyl-2-propylsulfanylpyrimidin-4(3H)-one
• 英文别名: 2-n-Propylthio-6-methyluracil；6-Methyl-2-n-propylthiouracil；6-methyl-2-propylthiopyrimidin-4(3H)-one；6-methyl-2-propylsulfanyl-3H-pyrimidin-4-one；6-Methyl-2-(propylthio)pyrimidin-4-ol；4-methyl-2-propylsulfanyl-1H-pyrimidin-6-one
• CAS: 62459-04-5
• 化学式: C₈H₁₂N₂OS
• mdl: MFCD00507249
• 分子量: 184.262
• InChiKey: LLFARFYEGBEUFC-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C(Solv: benzene (71-43-2))
• 沸点：
  289.6±23.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-碘代丙烷 、 6-甲基-2-(丙硫基)嘧啶-4-醇 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 以69%的产率得到6-methyl-4-propyloxy-2-propylsulfanylpyrimidine
  参考文献：
  名称：

  烷基卤化物和苄基卤化物中的卤素被4-羟基-2-巯基-6-甲基嘧啶生成的阴离子亲核取代的特殊特征

  摘要：

  The nucleophilic substitution of halogen (chlorine, bromine, and iodine) in alkyl and benzyl halides has been effected in aqueous dioxane media with S-and O-anions generated from 4-hydroxy-2-mercapto-6-methylpyrimidine. Under these conditions replacement of halogen proceeds by an S(N)2 mechanism and the reactivity of S-anions is 10 times greater than that of O-anions, which is in agreement with the results of ab initio quantum-chemical calculations of the electronic structure and total energy of transition states, carried out within the framework of the restricted Hartree-Fock method, basis 6-31G**.

  DOI：

  10.1007/s10593-008-0105-6
• 作为产物：
  描述：

  甲基硫脲嘧啶 、 1-碘代丙烷 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以94%的产率得到6-甲基-2-(丙硫基)嘧啶-4-醇
  参考文献：
  名称：

  Synthesis of 2-alkyl(aralkyl)sulfanyl-6-methylpyrimidin-4(3H)-ones and 4-alkyl(aralkyl)oxy-2-alkyl(aralkyl)sulfanyl-6-methylpyrimidines

  摘要：

  2-Alkyl(aralkyl)sulfanyl-6-methylpyrimidin-4(3H)-ones and 4-alkyl(aralkyl)oxy-2-alkyl(aralkyl)-sulfanyl-6-methylpyrimidines having similar or different substituents on the sulfur and oxygen atoms were synthesized by alkylation of sodium salts derived from 6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one and 2-alkyl(aralkyl)sulfanyl-6-methylpyrimidin-4(3H)-ones with alkyl (propyl, ethyl, allyl) and aralkyl [benzyl, m-phenoxybenzyl, p-(1-adamantylbenzyl)] halides. The effects of the alkyl (aralkyl) halide nature and solvent polarity on the rate of nucleophilic substitution and product yield were studied.

  DOI：

  10.1134/s1070428007010125

文献信息

• KULIEV, F. A.;GALSTYAN, K. A.;BABAXANOV, R. A., DOKL. AN AZSSR, 1985, 41, N 6, 27-28
  作者：KULIEV, F. A.、GALSTYAN, K. A.、BABAXANOV, R. A.

  DOI：——

  日期：——
• Special features of the nucleophilic substitution of halogen in alkyl and benzyl halides with anions generated from 4-hydroxy-2-mercapto-6-methylpyrimidine
  作者：A. I. Rakhimov、E. S. Titova、R. G. Fedunov、V. A. Babkin

  DOI：10.1007/s10593-008-0105-6

  日期：2008.6

  The nucleophilic substitution of halogen (chlorine, bromine, and iodine) in alkyl and benzyl halides has been effected in aqueous dioxane media with S-and O-anions generated from 4-hydroxy-2-mercapto-6-methylpyrimidine. Under these conditions replacement of halogen proceeds by an S(N)2 mechanism and the reactivity of S-anions is 10 times greater than that of O-anions, which is in agreement with the results of ab initio quantum-chemical calculations of the electronic structure and total energy of transition states, carried out within the framework of the restricted Hartree-Fock method, basis 6-31G**.
• Synthesis of 2-alkyl(aralkyl)sulfanyl-6-methylpyrimidin-4(3H)-ones and 4-alkyl(aralkyl)oxy-2-alkyl(aralkyl)sulfanyl-6-methylpyrimidines
  作者：A. I. Rakhimov、E. S. Titova

  DOI：10.1134/s1070428007010125

  日期：2007.1

  2-Alkyl(aralkyl)sulfanyl-6-methylpyrimidin-4(3H)-ones and 4-alkyl(aralkyl)oxy-2-alkyl(aralkyl)-sulfanyl-6-methylpyrimidines having similar or different substituents on the sulfur and oxygen atoms were synthesized by alkylation of sodium salts derived from 6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one and 2-alkyl(aralkyl)sulfanyl-6-methylpyrimidin-4(3H)-ones with alkyl (propyl, ethyl, allyl) and aralkyl [benzyl, m-phenoxybenzyl, p-(1-adamantylbenzyl)] halides. The effects of the alkyl (aralkyl) halide nature and solvent polarity on the rate of nucleophilic substitution and product yield were studied.