(4S,5R)-1-N-(phenylacetyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one | 169219-76-5

• 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: (4S,5R)-1-N-(phenylacetyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one
• 英文别名: (4R,5S)-1,5-dimethyl-4-phenyl-3-(2-phenylacetyl)imidazolidin-2-one
• CAS: 169219-76-5
• 化学式: C₁₉H₂₀N₂O₂
• 分子量: 308.38
• InChiKey: HABATTAOXHSFQS-KSSFIOAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5R)-1-N-(phenylacetyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 在 2,6-二甲基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 78.0h， 生成 (4R,5S,2'S)-3-(α-bromopropionyl)-1,5-dimethyl-4-phenylimidazolidin-2-one
  参考文献：
  名称：

  Synthesis of α-amino esters by dynamic kinetic resolution of α-haloacyl imidazolidinones

  摘要：

  Dynamic kinetic resolution of alpha -haloacyl imidazolidinones with a variety of nitrogen and carbon nucleophiles has been achieved with selectivities up to 100% (d.e.). An unusual dichotomy of diastereoselection has been observed whereby metalated nucleophiles preferentially react via the 5S,2 'R diastereomer whilst amine nucleophiles react via the 5S,2 'S diastereomer. Mild procedures are described for the coupling and removal of the ephedrine based chiral auxiliary. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00550-6
• 作为产物：
  描述：

  (4R,5S)-1,5-dimethyl-4-phenyl-3-[(2R)-2-pyrrolidin-1-ylpropanoyl]imidazolidin-2-one 在 2,6-二甲基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 生成 (4S,5R)-1-N-(phenylacetyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one
  参考文献：
  名称：

  Synthesis of α-amino esters by dynamic kinetic resolution of α-haloacyl imidazolidinones

  摘要：

  Dynamic kinetic resolution of alpha -haloacyl imidazolidinones with a variety of nitrogen and carbon nucleophiles has been achieved with selectivities up to 100% (d.e.). An unusual dichotomy of diastereoselection has been observed whereby metalated nucleophiles preferentially react via the 5S,2 'R diastereomer whilst amine nucleophiles react via the 5S,2 'S diastereomer. Mild procedures are described for the coupling and removal of the ephedrine based chiral auxiliary. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00550-6

文献信息

• The first enantioselective synthesis of isoflavonoids: (R)- and (S)-isoflavans
  作者：Marietjie Versteeg、Barend C. B. Bezuidenhoudt、Daneel Ferreira、Kenneth J. Swart

  DOI：10.1039/c39950001317

  日期：——

  α-Benzylation of (+)- and (–)-N-phenylacetyl imidazolidinones with 2-O-methoxymethylbenzyl bromide, followed by reductive removal of the chiral auxiliary and cyclization, leads to isoflavans in excellent enantiomeric excess and yield.

  (+)-和(-)-N-苯乙酰基咪唑烷酮与 2-O-甲氧基甲基溴化苄发生α-苄基化反应，然后还原去除手性助剂并进行环化反应，最终得到异黄酮，对映体过量，产量极高。
• Diastereoselective Addition of Imidazolidin-2-One Controlled Enolates to Activated Imines
  作者：Gregory H P Roos、Sundari Balasubramaniam

  DOI：10.1080/00397919908086028

  日期：1999.3

  Ephedrine-based imidazolidin-2-one chiral auxiliaries afford good syn stereoselectivity in the addition of their derived titanium enolates with an activated imine system. This provides entry into β-amino acid systems.

  基于麻黄碱的 imidazolidin-2-one 手性助剂通过将其衍生的钛烯醇化物与活化的亚胺体系相加，提供了良好的顺式立体选择性。这提供了进入β-氨基酸系统的入口。
• (4<i>S</i>,5<i>R</i>,2'<i>R</i>)-3,4-Dimethyl-1-[2'-(1-naphthyl)-2'-phenylacetyl]-5-phenylimidazolidin-2-one
  作者：R. Baggio、G. Lotz、S. Palacios、R. A. Mariezcurrena

  DOI：10.1107/s0108270198006453

  日期：1998.11.15

  The title compound, (4S,5R)-3,4-dimethyl-1-[(2R)-2(1-naphthyl)-2-phenylacetyl]-5-phenylimidazolidin-2-one, C29H26N2O2, has two different aryl groups at the alpha-carbon which confer a stereogenic character on the site. The geometry of the molecule is stabilized by an intramolecular hydrogen bond linking the acetamide and imidazolidine groups, which gives a planar character to the core.