3-((2S,4S,6S)-2,6-Dimethyl-[1,3]dioxan-4-yl)-1-methyl-1-phenyl-thiourea | 136157-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-((2S,4S,6S)-2,6-Dimethyl-[1,3]dioxan-4-yl)-1-methyl-1-phenyl-thiourea
• 英文别名: 3-[(2S,4S,6S)-2,6-dimethyl-1,3-dioxan-4-yl]-1-methyl-1-phenylthiourea
• CAS: 136157-94-3
• 化学式: C₁₄H₂₀N₂O₂S
• 分子量: 280.391
• InChiKey: GFMGKZFUCVFYIQ-GVXVVHGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,6-dimethyl-4-isothiocyanato-1,3-dioxane 、 N-甲基苯胺 以 乙醚 为溶剂， 反应 1.0h， 以60%的产率得到3-((2S,4S,6S)-2,6-Dimethyl-[1,3]dioxan-4-yl)-1-methyl-1-phenyl-thiourea
  参考文献：
  名称：

  Simple preparation of epimeric 2,6-dimethyl-4-(N′-substituted thioureido)-1,3-dioxanes and crystal structure of rel-2S,4S,6S-2,6-dimethyl-4-(N′-benzylthioureido)-1,3-dioxane

  摘要：

  One-pot reaction of acetaldehyde, KSCN and POCl3 affords 2,6-dimethyl-4-isothiocyanato-1,3-dioxane 4 in good yield. Compound 4 reacts with primary amines to give crystalline rel-2S,4R,6S-2,6-dimethyl-4-(N'-substituted thioureido)-1,3-dioxanes 5. The obtained thioureas 5 with axial thioureido group are spontaneously epimerised in acetone solution under formation of rel-2S,4S,6S-2,6-dimethyl-4-(N'-substituted thioureido)-1,3-dioxanes 6. These compounds form dimers containing relatively strong intermolecular hydrogen bonds -N-H...S- as confirmed by X-ray diffraction analysis. Treatment of isothiocyanate 4 with secondary amines is accompanied by epimerisation during the reaction and leads to a mixture of diastereoisomeric 5 and 6 or to pure diastereoisomers 6.

  DOI：

  10.1016/s0040-4020(01)86472-3

文献信息

• Simple preparation of epimeric 2,6-dimethyl-4-(N′-substituted thioureido)-1,3-dioxanes and crystal structure of rel-2S,4S,6S-2,6-dimethyl-4-(N′-benzylthioureido)-1,3-dioxane
  作者：Juraj Bernát、Ladislav Kniežo、Gabriela Birošová、Ján Imrich、Jaroslav Podlaha、Miloš Buděšínský、Jaromír Novák、Tibor Liptaj

  DOI：10.1016/s0040-4020(01)86472-3

  日期：1991.1

  One-pot reaction of acetaldehyde, KSCN and POCl3 affords 2,6-dimethyl-4-isothiocyanato-1,3-dioxane 4 in good yield. Compound 4 reacts with primary amines to give crystalline rel-2S,4R,6S-2,6-dimethyl-4-(N'-substituted thioureido)-1,3-dioxanes 5. The obtained thioureas 5 with axial thioureido group are spontaneously epimerised in acetone solution under formation of rel-2S,4S,6S-2,6-dimethyl-4-(N'-substituted thioureido)-1,3-dioxanes 6. These compounds form dimers containing relatively strong intermolecular hydrogen bonds -N-H...S- as confirmed by X-ray diffraction analysis. Treatment of isothiocyanate 4 with secondary amines is accompanied by epimerisation during the reaction and leads to a mixture of diastereoisomeric 5 and 6 or to pure diastereoisomers 6.