6-methyl-1-(thietan-3-yl)pyrimidine-2,4(1H,3H)-dione | 1443443-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-methyl-1-(thietan-3-yl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 6-Methyl-1-(thietan-3-yl)pyrimidine-2,4(1h,3h)-dione；6-methyl-1-(thietan-3-yl)pyrimidine-2,4-dione
• CAS: 1443443-01-3
• 化学式: C₈H₁₀N₂O₂S
• 分子量: 198.246
• InChiKey: CGYKRLPPOJCPOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methyl-1-(thietan-3-yl)pyrimidine-2,4(1H,3H)-dione 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 22.5h， 生成 2-[6-methyl-2,4-dioxo-1-(thietan-3-yl)-1,2,3,4-tetrahydropyrimidin-3-yl]acetic acid hydrazide
  参考文献：
  名称：

  尿嘧啶乙酸含硫腙的合成、异构和降压活性

  摘要：

  通过 2-[6-甲基-1-(thiethane-3-yl)uracil-3-yl] 乙酸酰肼与芳基醛和苯乙酮衍生物反应，得到了酰基腙，它以混合物的形式存在于 DMSO 溶液中EC=N-异构体的两个立体异构体，由于围绕酰肼键的内部旋转受阻。已经发现合成的化合物表现出降压活性。

  DOI：

  10.1134/s1068162014030108
• 作为产物：
  描述：

  2-(氯甲基)环硫乙烷 、 6-甲基尿嘧啶 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以29%的产率得到6-methyl-1-(thietan-3-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of thietanyl-substituted pyrimidine-2,4(1H,3H)-dions

  摘要：

  Reactions of 6-methylpyrimidine-2,4(1H,3H)-dione or 5-hydroxy-6-methyl-pyrimidine-2,4(1H,3H)-dione with 2-chloromethylthiirane afforded the corresponding substituted 1-(thietan-3-yl)pyrimidine-2,4(1H,3H)-diones. The calculations in the framework of approximations PBE/3z, B3LYP/6-31G++(d,p) and MP2/6-31G++(d,p) showed that the alkylation occurred at the atom N-1 of the pyrimidine ring.

  DOI：

  10.1134/s1070428013050199

文献信息

• Synthesis and structure of hydrazones obtained by the reaction of 2-[6-methyl-2,4-dioxo-1-(thietan-3-yl)-1,2,3,4-tetrahydropyrimidin-3-yl]acetic acide hydrazide with β-dicarbonyl compounds
  作者：S. A. Meshcheryakova、V. A. Kataev

  DOI：10.1134/s1070428014050157

  日期：2014.5

  Reaction of 2-[6-methyl-2,4-dioxo-1-(thietan-3-yl)-1,2,3,4-tetrahydropyrimidin-3-yl]acetic acid hydrazide with β-dicarbonyl compounds proceeds regioselectively; the structure of the formed hydrazones is governed by the structure of the β-dicarbonyl reaction component. The reaction with acetyl- and propionylacetone afforded 3-[2-(5-alkyl-3-methyl-1H-pyrazol-1-yl)-2-oxoethyl]-6-methyl-1-(thietan-3-yl)pyrimidin-2

  2- [6-甲基-2,4-二氧代-1-（噻吩-3-基）-1,2,3,4-四氢嘧啶-3-基]乙酸酰肼与β-二羰基化合物的反应是区域选择性的。形成的的结构受β-二羰基反应组分的结构支配。与乙酰基和丙酰基丙酮反应，得到3- [2-（5-烷基-3-甲基-1 H-吡唑-1-基）-2-氧代乙基] -6-甲基-1-（噻吩-3-基）嘧啶-2,4（1 H，3 H）-二酮与芳酰基丙酮，5-羟基吡唑啉衍生物，它们相对于酰胺键以E'构型存在于DMSO溶液中。与乙酰乙酸衍生物的缩合产物具有线性结构，由E，Z-和E'，Z'的混合物组成-异构体由于几何和构象异构。
• Synthesis of 3-(aminooxoethyl)-6-methyl-1-(thiethan-3-yl)-pyrimidine-2,4-(1H,3H)-diones
  作者：S. A. Meshcheryakova

  DOI：10.1134/s1070363214080179

  日期：2014.8

  A new approach to prepare 2-chloroacetamides has been developed, based on the reaction of chloroacetyl chloride with excess of secondary amines. Alkylation of 6-methyl-1-(thiethan-3-yl)pyrimidine-2,4(1H,3H)-dione with the synthesized 2-chloroacetamides in the presence of potassium carbonate has afforded N-3-acetamido-substituted 6-methyl-1-(thiethan-3-yl) pyrimidine-2,4(1H,3H)-diones.
• Oxidation and isomerism of thietane-containing heterocycles
  作者：S. A. Meshcheryakova、V. A. Kataev、D. A. Munasipova、I. Ya. Fattakhova

  DOI：10.1134/s1070363214050144

  日期：2014.5

  Oxidation of 6-methyl-1-(thiethan-3-yl)pyrimidine-2,4(1H,3H)-dione, 5(6)-nitro-1-(thiethan-3-yl)-benzimidazole, 2-methyl-4-nitro-1-(thiethan-3-yl)- and 5-bromo-2-methyl-4-nitro-1-(thiethan-3-yl)imidazoles was examined. Corresponding 1-oxothietan-3-yl- and 1,1-dioxothietan-3-yl derivatives were synthesized for the first time. Some factors affecting the quality of the final products and optimal conditions of the oxidation of thietanyl derivatives of pyrimidine-2,4(1H,3H)-dione, nitrobenzimidazole, and nitroimidazole were found. According to 1H NMR spectroscopy data, the obtained sulfoxides are mixtures of cis/trans isomers, the diastereomers ratio determined by the substituent at position 3 of thietane ring.
• Aminomethylation of 6-methyl-1-(thietan-3-yl)pyrimidine-2,4(1H,3H)-dione
  作者：S. A. Meshcheryakova、V. A. Kataev、D. A. Munasipova

  DOI：10.1134/s1070428014030208

  日期：2014.3

  Mannich reactions of 6-methyl-1-(thietan-3-yl)pyrimidine-2,4(1H,3H)-dione with formaldehyde and morpholine, piperidine, N-methylpiperazine, and diethylamine gave the corresponding 5-aminomethylsubstituted pyrimidine derivatives. The title compound reacted with excess piperazine to form 3,5-bis-(piperazin-1-yl) derivative, while its reaction with an equimolar amount of piperazine afforded 5,5'-(piperazin-1,4-diylbismethylene)bis[6-methyl-1-(thietan-3-yl)pyrimidine-2,4(1H,3H)-dione].