1,3-dibutanoyl-trans-4,5-tetramethyleneimidazolidin-2-one | 137618-13-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3-dibutanoyl-trans-4,5-tetramethyleneimidazolidin-2-one
• 英文别名: (3aR,7aR)-1,3-di(butanoyl)-3a,4,5,6,7,7a-hexahydrobenzimidazol-2-one
• CAS: 137618-13-4；139122-02-4；140850-24-4
• 化学式: C₁₅H₂₄N₂O₃
• 分子量: 280.367
• InChiKey: GPCKUCJZIMWXNN-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  碘甲烷 、 1,3-dibutanoyl-trans-4,5-tetramethyleneimidazolidin-2-one 在 双(三甲基硅烷基)氨基钾 作用下， 生成 (3aR,7aR)-1,3-bis(2-methylbutanoyl)-3a,4,5,6,7,7a-hexahydrobenzimidazol-2-one
  参考文献：
  名称：

  Bifunctional chiral auxiliaries 4: Alkylation of enolates derived from 1,3-diacyl-trans-4,5-tetramethyleneimidazolidin-2-ones

  摘要：

  Addition of alkyl halides to sodium and potassium enolates of 1,3-diacyl-trans-4,5-tetramethyleneimidazolidin-2-ones allows diastereoselective alkylation of both acyl sidechains with the latter enolates showing generally higher stereoselectivities. S-(-)-3-Phenyl-2-methylpropan-1-ol 6 was prepared in this way with a 93% enantiomeric excess.

  DOI：

  10.1016/s0040-4039(00)91875-6
• 作为产物：
  描述：

  trans-1,2-Diaminocyclohexane 在 吡啶 、 4-二甲氨基吡啶 、 mercury(II) diacetate 作用下， 以 二氯甲烷 为溶剂， 生成 1,3-dibutanoyl-trans-4,5-tetramethyleneimidazolidin-2-one
  参考文献：
  名称：

  Bifunctional chiral auxiliaries 2: the synthesis of 1,3-diacylimidazolidin-2-ones from 1,2-diamines

  摘要：

  The title compounds are readily prepared in three steps via the corresponding 1,3-diacylimidazolidine-2-thiones. The final step involves the novel use of mercury (II) acetate for the conversion of thioureas to ureas.

  DOI：

  10.1016/s0040-4039(00)92309-8

文献信息

• Bifunctional chiral auxiliaries 6: Alkylations of enolates derived from 1,3-diacylimidazolidine- 2-thiones and 1,3-diacylimidazolidin-2-ones
  作者：Stephen G. Davies、Gary B. Evans、Andrew A. Mortlock

  DOI：10.1016/0957-4166(94)80022-7

  日期：1994.4

  Sodium and potassium enolates of 1,3-diacylimidazolidin-2-ones undergo clean alkylation reactions with reactive alkyl halides; the latter enolates reacting generally more stereoselectively due, it is proposed, to the lower temperature at which the reactions proceed. The reactions are all stereoregular, with the diastereoisomeric identity of products being established unambiguously by the synthesis

  1,3-二酰基咪唑烷基-2-酮的烯醇钠和钾盐与反应性烷基卤化物进行干净的烷基化反应；提议的是，后者由于反应进行的较低温度而通常更立体选择性地发生反应。反应都是立体有规的，通过（2S）-3-苯基-2-甲基丙烷-1-醇的合成可以明确地确定产物的非对映异构身份。在这些反应中的不对称诱导的意义上是与螯合的中间性一致的顺式烯醇化物其中亲电子从面部优先接近外在五元环上的最接近的烷基/芳基上。相反，由于烯醇盐的分解，在烷基化反应中1，3-二酰基咪唑烷-2-硫酮不能作为双官能手性助剂。
• Bifunctional chiral auxiliaries 5: The synthesis of 1,3-diacylimidazolidine-2-thiones and 1,3-diacylimidazolidin-2-ones from 1,2-diamines
  作者：Stephen G. Davies、Andrew A. Mortlock

  DOI：10.1016/s0040-4020(01)85757-4

  日期：1993.1

  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.