diethyl 2-chloro-1-[(cyclohexylidenemethyl)(methoxycarbonyl)amino]ethylphosphonate | 946603-27-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl 2-chloro-1-[(cyclohexylidenemethyl)(methoxycarbonyl)amino]ethylphosphonate
• CAS: 946603-27-6
• 化学式: C₁₅H₂₇ClNO₅P
• 分子量: 367.81
• InChiKey: VPISITBGVWNWOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diethyl 2-chloro-1-[(cyclohexylidenemethyl)(methoxycarbonyl)amino]ethylphosphonate 在 氨 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 152.0h， 生成 3-(Cyclohexylidenemethyl)-4-[diethoxy(oxido)phosphaniumyl]-1-prop-2-enylimidazolidin-2-one
  参考文献：
  名称：

  Ring transformations of aziridinyl 2-phosphonates: synthesis of 5-phosphono-2-oxazolidinones and 5-phosphono-2-imidazolidinones

  摘要：

  Syntheses of 5-phosphono-2-oxazolidinones and 5-phosphono-2-imidazolidinones were achieved from the corresponding 1-vinyl-2-phosphonoaziridines. Regioselective aziridine ring opening employing methyl chloroformate affords 1-amido-2-chloroethyl-phosphonates, which were easily transformed into the corresponding 2-oxazolidinones upon heating in dimethyl sulfoxide. Treatment of the aziridine ring opening products with ammonia furnishes vinylphosphonates, which undergo a Michael type addition with several amines. In situ ring closure of the addition products yields the corresponding phosphonylated 2-imidazolidinones. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.023
• 作为产物：
  描述：

  氯甲酸甲酯 、 2-diethylphosphono-1-(cyclohexylidenemethyl)aziridine 以 二氯甲烷 为溶剂， 反应 24.0h， 以50%的产率得到diethyl 2-chloro-1-[(cyclohexylidenemethyl)(methoxycarbonyl)amino]ethylphosphonate
  参考文献：
  名称：

  Ring transformations of aziridinyl 2-phosphonates: synthesis of 5-phosphono-2-oxazolidinones and 5-phosphono-2-imidazolidinones

  摘要：

  Syntheses of 5-phosphono-2-oxazolidinones and 5-phosphono-2-imidazolidinones were achieved from the corresponding 1-vinyl-2-phosphonoaziridines. Regioselective aziridine ring opening employing methyl chloroformate affords 1-amido-2-chloroethyl-phosphonates, which were easily transformed into the corresponding 2-oxazolidinones upon heating in dimethyl sulfoxide. Treatment of the aziridine ring opening products with ammonia furnishes vinylphosphonates, which undergo a Michael type addition with several amines. In situ ring closure of the addition products yields the corresponding phosphonylated 2-imidazolidinones. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.023