(R,R)-(+)-1,3-dipropionyl-trans-4,5-diphenylimidazolidin-2-one | 138808-81-8

• 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: (R,R)-(+)-1,3-dipropionyl-trans-4,5-diphenylimidazolidin-2-one
• 英文别名: (R,R)-(-)-1,3-dipropionyl-trans-4,5-diphenylimidazolidin-2-one；1,3-dipropionyl-trans-4,5-diphenylimidazolidin-2-one；(4R,5R)-4,5-diphenyl-1,3-di(propanoyl)imidazolidin-2-one
• CAS: 138808-81-8
• 化学式: C₂₁H₂₂N₂O₃
• 分子量: 350.417
• InChiKey: PJDQVUAKXVUPGY-WOJBJXKFSA-N

物化性质

• 沸点：
  483.3±55.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,R)-(+)-1,3-dipropionyl-trans-4,5-diphenylimidazolidin-2-one 生成 (4R,5R)-4,5-二苯基-2-咪唑烷酮
  参考文献：
  名称：

  Bifunctional chiral auxiliaries 3: Synthesis of homochiral 1,3-diols via asymmetric aldol reactions of dialkylboron enolates of 1,3-dipropionyl-trans-4,5-diphenyl-imidazolidin-2-one and aldehydes

  摘要：

  Dibutylboron enolates derived from both racemic and homochiral 1,3-dipropionyl-trans-4,5-diphenylimidazolidin-2-one 3 react with aldehydes in highly diastereoselective dialdol reactions to give, after reductive cleavage of the acyl sidechain, substituted 1,3-diols.

  DOI：

  10.1016/s0957-4166(00)86148-0
• 作为产物：
  描述：

  (R,R)-1,3-dipropionyl-trans-4,5-diphenylimidazolidine-2-thione 在 mercury(II) diacetate 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到(R,R)-(+)-1,3-dipropionyl-trans-4,5-diphenylimidazolidin-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

文献信息

• Bifunctional chiral auxiliaries 7: Aldol reactions of enolates derived from 1,3-diacyl-imidazolidine-2-thiones and 1,3-diacylimidazolidin-2-ones
  作者：Stephen G. Davies、Alison J. Edwards、Gary B. Evans、Andrew A. Mortlock

  DOI：10.1016/s0040-4020(01)89691-5

  日期：——

  Dibutylboron enolates of 1,3-diacylimidazolidine-2-thiones and 1,3-diacylimidazolidin-2-ones undergo highly syn-stereoselective aldol reactions with aldehydes to allow elaboration of both acyl sidechains. The reaction is proposed to occur via sequential enolisation rather than via a bisenolate and the stereochemistry of the product was elucidated by both X-ray crystallography and reductive cleavage

  烯醇化物二丁基1,3- diacylimidazolidine -2-硫酮和1,3- diacylimidazolidin -2-酮离岗高度顺式与醛-stereoselective羟醛缩合反应，从而允许其酰基侧链的阐述。建议该反应通过顺序烯醇化而不是通过二烯酸酯来进行，并且该产物的立体化学通过X射线晶体学和同手性羟醛产物的还原裂解来阐明，以给出（1 R，2 S）-1-苯基- 2-甲基丙烷-1,3-二醇。相比之下，三氟甲磺酸锡（II）介导的醛醇缩合反应仅导致两个酰基侧链之一发生反应，并展现出相反的对面立体选择性。