diethyl 3-(cyclohexylidenemethyl)-2-oxo-1,3-oxazolidin-4-ylphosphonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl 3-(cyclohexylidenemethyl)-2-oxo-1,3-oxazolidin-4-ylphosphonate
• 英文别名: 3-(Cyclohexylidenemethyl)-4-[diethoxy(oxido)phosphaniumyl]-1,3-oxazolidin-2-one；3-(cyclohexylidenemethyl)-4-[diethoxy(oxido)phosphaniumyl]-1,3-oxazolidin-2-one
• 化学式: C₁₄H₂₄NO₅P
• 分子量: 317.322
• InChiKey: AKNHFDXJRDVHAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-diethylphosphono-1-(cyclohexylidenemethyl)aziridine 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 64.0h， 生成 diethyl 3-(cyclohexylidenemethyl)-2-oxo-1,3-oxazolidin-4-ylphosphonate
  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

文献信息

• Ring transformations of aziridinyl 2-phosphonates: synthesis of 5-phosphono-2-oxazolidinones and 5-phosphono-2-imidazolidinones
  作者：Bart Vanderhoydonck、Christian V. Stevens

  DOI：10.1016/j.tet.2007.05.023

  日期：2007.8

  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.