(2'RS,4S,5R)-1-N-(2'bromobutanoyl)-3,4-dimethyl-5-phenylimidazolidin-2-one | 206358-47-6

• 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: (2'RS,4S,5R)-1-N-(2'bromobutanoyl)-3,4-dimethyl-5-phenylimidazolidin-2-one
• 英文别名: (4S,5R)-1-(2-bromobutanoyl)-3,4-dimethyl-5-phenylimidazolidin-2-one
• CAS: 206358-47-6
• 化学式: C₁₅H₁₉BrN₂O₂
• 分子量: 339.232
• InChiKey: BXRYTPOMWGUHDR-VLIRHVTKSA-N

物化性质

• 沸点：
  404.0±55.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (2'RS,4S,5R)-1-N-(2'bromobutanoyl)-3,4-dimethyl-5-phenylimidazolidin-2-one 在 2,6-二甲基吡啶 、 四丁基碘化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 192.42h， 生成 (2'R,4S,5R)-1-N-(2'bromohexanoyl)-3,4-dimethyl-5-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：

  2-溴丁酰溴 、 (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以32%的产率得到(2'RS,4S,5R)-1-N-(2'bromobutanoyl)-3,4-dimethyl-5-phenylimidazolidin-2-one
  参考文献：
  名称：

  A PRACTICAL METHOD FOR THE ACYLATION OF 2-IMIDAZOLIDINONE AND 2-OXAZOLIDINONE CHIRAL AUXILIARIES WITH 2- BROMOACYL HALIDES

  摘要：

  Optimised conditions for the acylation of (S)-4-(1-methylethyl) -oxazolidin-2-one 4, (R)-4-phenyloxazolidin-2-one 5 and 4-(R), (5S)-1,5-dimethyl-4-phenylimidazolidin-2-one 3 with 2-bromoacyl halides were developed. For imidazolidin-2-one 3 the optimum conditions require the use of the hindered bases2,6-di-t-butylpyridine or 2,6-lutidine in order to reduce the ketene formation which has a strong preference for O-acylation.

  DOI：

  10.1081/scc-100106033

文献信息

• Rationalising diastereoselection in the dynamic kinetic resolution of α-haloacyl imidazolidinones
  作者：Stephen Caddick、Kerry Jenkins、Nigel Treweeke、Sara X. Candeias、Carlos A.M. Afonso

  DOI：10.1016/s0040-4039(98)00175-0

  日期：1998.4

  A crossover from S(N)2 to general base catalysed nucleophilic substitution can account for the dichotomous diastereoselectivity observed in DKR reactions of alpha-haloacyl imidazolidinones. Aprotic nucleophiles (Nu(-)) react preferentially with the 5S*,2'R* diastereomer via an S(N)2 mechanism. Conversely, amines (R2NH) generally react preferentially with the 5S*,2'S* diastereomer. General base catalysis via a bifurcated hydrogen bonded assembly accounts for this anomalous stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.