5-乙基-2,3-二氢-5-(3-甲基丁基)-2-硫代-4,6(1H,5H)-嘧啶二酮 | 4388-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-乙基-2,3-二氢-5-(3-甲基丁基)-2-硫代-4,6(1H,5H)-嘧啶二酮
• 英文名称: 5-ethyl-5-(3-methylbutyl)-2-thiobarbituric acid
• 英文别名: 5-ethyl-5-(3-methyl-butyl)-2-thioxo-dihydro-pyrimidine-4,6-dione；5-ethyl-5-isopentyl-2-thio-barbituric acid；5-Aethyl-5-isopentyl-2-thio-barbitursaeure；5-Ethyl-5-isoamyl-2-thiobarbitursaeure；Thioamobarbital；5-ethyl-5-(3-methylbutyl)-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 4388-79-8
• 化学式: C₁₁H₁₈N₂O₂S
• 分子量: 242.342
• InChiKey: NGXZRVUMBBHGBE-UHFFFAOYSA-N

物化性质

• 熔点：
  167-169 °C
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  90.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-乙基-2,3-二氢-5-(3-甲基丁基)-2-硫代-4,6(1H,5H)-嘧啶二酮 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以82%的产率得到5-ethyl-5-isoamylhexahydropyrimidine-4,6-dione
  参考文献：
  名称：

  Desulfurization of thioureas, benzimidazoline-2-thiones and 1,3-dihydro-1,3-diaryl-2-thioxopyrimidine-4,6(2H,5H)-diones with nickel boride at ambient temperature1

  摘要：

  镍硼化物被报道能促使N,N′-二芳基硫脲的脱硫和还原 cleavage，从而生成相应的苯胺和N-甲基苯胺，而N,N′-二烷基硫脲被观察到可以脱硫生成甲酰胺；还报道了苯并咪唑啉-2-硫酮能够脱硫生成苯并咪唑，而1,3-二氢-1,3-二芳基-2-硫代嘧啶-4,6(2H,5H)-二酮则在干甲醇中于室温下高产率地生成相应的六氢嘧啶-4,6-二酮。

  DOI：

  10.1039/b206398k
• 作为产物：
  描述：

  硫脲 、 乙基异戊基丙二酸二乙酯 在 sodium ethanolate 作用下， 生成 5-乙基-2,3-二氢-5-(3-甲基丁基)-2-硫代-4,6(1H,5H)-嘧啶二酮
  参考文献：
  名称：

  US2153711

  摘要：

  公开号：

文献信息

• Reductive Desulfurization of Thiohydantoins and Thiobarbituric Acids with Raney Nickel
  作者：W. B. Whalley、Elvin L. Anderson、F. DuGan、James W. Wilson、Glenn E. Ullyot

  DOI：10.1021/ja01608a056

  日期：1955.2.1
• Sulfur-Containing Barbiturate Hypnotics
  作者：D. L. Tabern、E. H. Volwiler

  DOI：10.1021/ja01313a062

  日期：1935.10
• Competition between two metabolic pathways: oxidation and desulfuration in the thiobarbiturate series
  作者：A Yebga、S Ménager、P Vérité、C Combet Farnoux、O Lafont

  DOI：10.1016/0223-5234(96)88296-1

  日期：1995.1

  In order to study the competition between hepatic hydroxylation and desulfuration in the thiobarbiturate series, two compounds bearing a branched side chain with a tertiary carbon atom in position omega-1 were administered to rats over about one week, Urine and faeces were collected and extracted. The metabolites isolated were identified. It was shown that desulfuration was not the major metabolic pathway, and that, when it took place, it remained a minor process and was accompanied by gamma-hydroxylation into a tertiary alcohol.
• US2153711
  申请人：——

  公开号：——

  公开（公告）日：——
• Desulfurization of thioureas, benzimidazoline-2-thiones and 1,3-dihydro-1,3-diaryl-2-thioxopyrimidine-4,6(2H,5H)-diones with nickel boride at ambient temperature1
  作者：Jitender M. Khurana、Gagan Kukreja、Geeti Bansal

  DOI：10.1039/b206398k

  日期：2002.11.13

  Nickel boride is reported to bring about desulfurization and reductive cleavage of N,N′-diarylthioureas to give corresponding anilines and N-methylanilines while N,N′-dialkylthioureas have been observed to undergo desulfurization to give formamidines; benzimidazoline-2-thiones are reported to undergo desulfurization to benzimidazoles and 1,3-dihydro-1,3-diaryl-2-thioxopyrimidine-4,6(2H,5H)-diones have been observed to yield corresponding hexahydropyrimidine-4,6-diones in high yields in dry methanol at ambient temperature.

  镍硼化物被报道能促使N,N′-二芳基硫脲的脱硫和还原 cleavage，从而生成相应的苯胺和N-甲基苯胺，而N,N′-二烷基硫脲被观察到可以脱硫生成甲酰胺；还报道了苯并咪唑啉-2-硫酮能够脱硫生成苯并咪唑，而1,3-二氢-1,3-二芳基-2-硫代嘧啶-4,6(2H,5H)-二酮则在干甲醇中于室温下高产率地生成相应的六氢嘧啶-4,6-二酮。