(R,R)-(-)-1,3-dipropionyl-trans-4,5-tetramethyleneimidazolidine-2-thione | 139237-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (R,R)-(-)-1,3-dipropionyl-trans-4,5-tetramethyleneimidazolidine-2-thione
• 英文别名: 1-[(3aR,7aR)-3-propanoyl-2-sulfanylidene-3a,4,5,6,7,7a-hexahydrobenzimidazol-1-yl]propan-1-one
• CAS: 139237-83-5
• 化学式: C₁₃H₂₀N₂O₂S
• 分子量: 268.38
• InChiKey: ILSXLZKTXVSALB-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  40.62
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R,R)-(-)-1,3-dipropionyl-trans-4,5-tetramethyleneimidazolidine-2-thione 在 mercury(II) diacetate 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到1,3-dipropionyl-trans-4,5-tetramethyleneimidazolin-2-one
  参考文献：
  名称：

  Bifunctional chiral auxiliaries 5: The synthesis of 1,3-diacylimidazolidine-2-thiones and 1,3-diacylimidazolidin-2-ones from 1,2-diamines

  摘要：

  Although 1,2-diamines fail to cyclise with urea, phosgene or 1,1'-carbonyl diimidazole, they react with carbon disulphide to give the corresponding imidazolidine-2-thiones. These undergo clean diacylation to give 1,3-diacylimidazolidine-2-thiones which are readily converted to 1,3-diacylimidazolidin-2-ones on treatment with mercury (II) acetate. An alternative two-step route to 1,3-diacylimidazolidin-2-ones uses carbonyl sulphide to effect cyclisation of the 1,2-diamine to the imidazolidin-2-one, which is subsequently diacylated. The ability to convert homochiral 1,2-diamines to homochiral 1,3-diacylimidazolidin-2-ones has also been demonstrated.

  DOI：

  10.1016/s0040-4020(01)85757-4
• 作为产物：
  描述：

  (1R,2R)-1,2-diaminocyclohexane 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 (R,R)-(-)-1,3-dipropionyl-trans-4,5-tetramethyleneimidazolidine-2-thione
  参考文献：
  名称：

  Bifunctional chiral auxiliaries 5: The synthesis of 1,3-diacylimidazolidine-2-thiones and 1,3-diacylimidazolidin-2-ones from 1,2-diamines

  摘要：

  Although 1,2-diamines fail to cyclise with urea, phosgene or 1,1'-carbonyl diimidazole, they react with carbon disulphide to give the corresponding imidazolidine-2-thiones. These undergo clean diacylation to give 1,3-diacylimidazolidine-2-thiones which are readily converted to 1,3-diacylimidazolidin-2-ones on treatment with mercury (II) acetate. An alternative two-step route to 1,3-diacylimidazolidin-2-ones uses carbonyl sulphide to effect cyclisation of the 1,2-diamine to the imidazolidin-2-one, which is subsequently diacylated. The ability to convert homochiral 1,2-diamines to homochiral 1,3-diacylimidazolidin-2-ones has also been demonstrated.

  DOI：

  10.1016/s0040-4020(01)85757-4