(4S*,5S*)-4,5-dihydroxy-1-methylimidazolidine-2-thione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S*,5S*)-4,5-dihydroxy-1-methylimidazolidine-2-thione
• 英文别名: (4R,5R)-4,5-dihydroxy-1-methylimidazolidine-2-thione
• 化学式: C₄H₈N₂O₂S
• 分子量: 148.186
• InChiKey: PMLULKKCEWWGHV-PWNYCUMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  87.8
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S*,5S*)-4,5-dihydroxy-1-methylimidazolidine-2-thione 、 potassium thioacyanate 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以92%的产率得到(3aR*,6aS*)-1-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione
  参考文献：
  名称：

  New access to thioglycolurils by condensation of 4,5-dihydroxyimidazolidin-2-ones(thiones) with HSCN

  摘要：

  A general and highly effective protocol for the direct synthesis of mono- and dithioglycolurils containing various substituents at the 1,3-nitrogen atoms has been developed based on the condensation of easily accessible dihydroxyimidazolidin-2-ones with HSCN under mild reactions conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.09.071
• 作为产物：
  描述：

  草酸醛 、 N-甲硫脲 以 水 为溶剂， 反应 1.0h， 以40%的产率得到(4S*,5S*)-4,5-dihydroxy-1-methylimidazolidine-2-thione
  参考文献：
  名称：

  New access to thioglycolurils by condensation of 4,5-dihydroxyimidazolidin-2-ones(thiones) with HSCN

  摘要：

  A general and highly effective protocol for the direct synthesis of mono- and dithioglycolurils containing various substituents at the 1,3-nitrogen atoms has been developed based on the condensation of easily accessible dihydroxyimidazolidin-2-ones with HSCN under mild reactions conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.09.071

文献信息

• Regioselective synthesis of 1-alkyl-4-methylsemithioglycolurils
  作者：Anton A. Galochkin、Alisa E. Pavlovskaya、Vladimir V. Baranov、Yurii A. Strelenko、Angelina N. Kravchenko

  DOI：10.1007/s10593-022-03134-2

  日期：2022.11

  The regioselective reaction of 4,5-dihydroxy-1-methylimidazolidine-2-thione with 1-alkylureas was explored for the first time, predominantly providing the previously inaccessible 1-alkyl-4-methylsemithioglycolurils as the major products. We demonstrated that the interaction of the reactants was accompanied by the formation of isomeric 1-alkyl-6-methylsemithioglycolurils and several known compounds:

  首次探索了 4,5-二羟基-1-甲基咪唑啉-2-硫酮与 1-烷基脲的区域选择性反应，主要提供以前无法获得的 1-烷基-4-甲基半硫甘脲作为主要产物。我们证明了反应物的相互作用伴随着异构 1-alkyl-6-methylsemithioglycolurils 和几种已知化合物的形成：1-methyl- 和 3-methylthiohydantoin，1-methyl-1 H -imidazole-2(3 H ) -硫酮和 1,4-二取代甘脲作为副产品。4,5-dihydroxy-1-methylimidazolidine-2-thione 与 1-isopropylurea 的反应也产生了 1,1'-(1-methyl-2-thioxoimidazolidine-4,5-diyl)bis(3-isopropylurea) 的混合物) 非对映异构体。