(4S,5R)-1-(2',2'-dibromoethanoyl)-3,4-dimethyl-5-phenylimidazolidin-2-one | 389119-16-8

• 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: (4S,5R)-1-(2',2'-dibromoethanoyl)-3,4-dimethyl-5-phenylimidazolidin-2-one
• 英文别名: 2-Imidazolidinone, 1-(dibromoacetyl)-3,4-dimethyl-5-phenyl-, (4S,5R)-；(4S,5R)-1-(2,2-dibromoacetyl)-3,4-dimethyl-5-phenylimidazolidin-2-one
• CAS: 389119-16-8
• 化学式: C₁₃H₁₄Br₂N₂O₂
• 分子量: 390.074
• InChiKey: XWWFYRJHKYUOGU-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one 、 溴乙酰溴 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以24%的产率得到(4S,5R)-1-(2'-bromoethanoyl)-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

• A PRACTICAL METHOD FOR THE ACYLATION OF 2-IMIDAZOLIDINONE AND 2-OXAZOLIDINONE CHIRAL AUXILIARIES WITH 2- BROMOACYL HALIDES
  作者：Sara X. Candeias、Kerry Jenkins、A. S. C. Ribeiro、Carlos A. M. Afonso、Stephen Caddick

  DOI：10.1081/scc-100106033

  日期：2001.1

  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.