(R,R)-(+)-1,3-dipropionyl-trans-4,5-diphenylimidazolidin-2-one | 137618-21-4

• 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: 1,3-dipropionyl-trans-4,5-diphenylimidazolidin-2-one
• CAS: 137618-21-4；138808-81-8；139237-80-2
• 化学式: C₂₁H₂₂N₂O₃
• 分子量: 350.417
• InChiKey: PJDQVUAKXVUPGY-PMACEKPBSA-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)：
  4.08
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  苯甲醛 、 (R,R)-(+)-1,3-dipropionyl-trans-4,5-diphenylimidazolidin-2-one 生成 (4S,5S)-1,3-Bis-((2S,3S)-3-hydroxy-2-methyl-3-phenyl-propionyl)-4,5-diphenyl-imidazolidin-2-one
  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：

  (1R,2R)-1,2-二苯基乙二胺 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 (R,R)-(+)-1,3-dipropionyl-trans-4,5-diphenylimidazolidin-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 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。
• 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.