diethyl 3-(4-methoxybenzoyl)oxy-1(E)-propenylphosphonate | 202476-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl 3-(4-methoxybenzoyl)oxy-1(E)-propenylphosphonate
• 英文别名: [(E)-3-diethoxyphosphorylprop-2-enyl] 4-methoxybenzoate
• CAS: 202476-38-8
• 化学式: C₁₅H₂₁O₆P
• 分子量: 328.302
• InChiKey: PVSABWUZQDUONY-WUXMJOGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  22.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  diethyl 3-(4-methoxybenzoyl)oxy-1(E)-propenylphosphonate 在 potassium osmate(VI) AD-mix-α 、 甲基磺酰胺 作用下， 以 水 、 叔丁醇 为溶剂， 反应 50.0h， 以10%的产率得到diethyl (1S,2S)-1,2-dihydroxy-3-(4-methoxybenzoyloxy)propylphosphonate
  参考文献：
  名称：

  Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents

  摘要：

  Asymmetric dihydroxylation (AD) of 1(E)-alkenylphosphonates with an AD-mix -alpha or -beta reagent was examined to give a series of optically active threo-alpha,beta-dihydroxyphosphonates. Good enantioselectivity (>88% eel was observed in the AD reaction of 1(E)-alkenylphosphonates with conjugated aromatic substituents. The steric effects of the ester functionality in the course of the dihydroxylation were also evaluated. Enantioselectivity and yield were significantly improved when the AD reaction was carried out with dimethyl phosphonate instead of diethyl phosphonate. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10341-6
• 作为产物：
  描述：

  3-溴-1-丙烯膦酸二乙酯 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 丁酮 为溶剂， 反应 27.0h， 生成 diethyl 3-(4-methoxybenzoyl)oxy-1(E)-propenylphosphonate
  参考文献：
  名称：

  Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents

  摘要：

  Asymmetric dihydroxylation (AD) of 1(E)-alkenylphosphonates with an AD-mix -alpha or -beta reagent was examined to give a series of optically active threo-alpha,beta-dihydroxyphosphonates. Good enantioselectivity (>88% eel was observed in the AD reaction of 1(E)-alkenylphosphonates with conjugated aromatic substituents. The steric effects of the ester functionality in the course of the dihydroxylation were also evaluated. Enantioselectivity and yield were significantly improved when the AD reaction was carried out with dimethyl phosphonate instead of diethyl phosphonate. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10341-6