(+/-)-diisopropyl 2-bromo-1-hydroxyethylphosphonate | 300590-29-8

• 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: (+/-)-diisopropyl 2-bromo-1-hydroxyethylphosphonate
• 英文别名: 2-Bromo-1-di(propan-2-yloxy)phosphorylethanol
• CAS: 300590-29-8
• 化学式: C₈H₁₈BrO₄P
• 分子量: 289.106
• InChiKey: NQXXGTIYAYUJDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-diisopropyl 2-bromo-1-hydroxyethylphosphonate 在 吡啶 、 sodium azide 、 18-冠醚-6 作用下， 以 乙腈 为溶剂， 反应 82.0h， 生成 (+/-)-diisopropyl 2-azido-1-acetoxyethylphosphonate
  参考文献：
  名称：

  Enzymes in organic chemistry. Part 10: Chemo-enzymatic synthesis of l-phosphaserine and l-phosphaisoserine and enantioseparation of amino-hydroxyethylphosphonic acids by non-aqueous capillary electrophoresis with quinine carbamate as chiral ion pair agent

  摘要：

  Diisopropyl 2-azido-1-acetoxyethylphosphonate (+/-)-7 was hydrolysed with high enantioselectivity by lipase SP 524 to give alpha-hydroxyphosphonate (S)-(-)-6 and ester (R)-(-)-7, which was saponified to give (R)-(+)-6. The two alpha-hydroxyphosphonates (R)- and (S)-6 were transformed into 1-phosphaisoserine and L-phosphaserine, respectively. Their enantiomeric excesses were determined to be 97% by HPLC on an chiral stationary phase. A mixture of all four stereoisomeric amino-hydroxyethylphosphonic acids can be separated by non-aqueous capillary electrophoresis with quinine carbamate as the chiral ion pair agent applying the partial filling technique. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00261-5
• 作为产物：
  描述：

  diisopropyl trimethylsily phosphite 、 溴乙酸乙酯 在 二异丁基氢化铝 作用下， 以 正庚烷 、 甲苯 为溶剂， 反应 2.0h， 以58%的产率得到(+/-)-diisopropyl 2-bromo-1-hydroxyethylphosphonate
  参考文献：
  名称：

  Enzymes in organic chemistry. Part 10: Chemo-enzymatic synthesis of l-phosphaserine and l-phosphaisoserine and enantioseparation of amino-hydroxyethylphosphonic acids by non-aqueous capillary electrophoresis with quinine carbamate as chiral ion pair agent

  摘要：

  Diisopropyl 2-azido-1-acetoxyethylphosphonate (+/-)-7 was hydrolysed with high enantioselectivity by lipase SP 524 to give alpha-hydroxyphosphonate (S)-(-)-6 and ester (R)-(-)-7, which was saponified to give (R)-(+)-6. The two alpha-hydroxyphosphonates (R)- and (S)-6 were transformed into 1-phosphaisoserine and L-phosphaserine, respectively. Their enantiomeric excesses were determined to be 97% by HPLC on an chiral stationary phase. A mixture of all four stereoisomeric amino-hydroxyethylphosphonic acids can be separated by non-aqueous capillary electrophoresis with quinine carbamate as the chiral ion pair agent applying the partial filling technique. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00261-5

文献信息

• Enzymes in organic chemistry. Part 10: Chemo-enzymatic synthesis of l-phosphaserine and l-phosphaisoserine and enantioseparation of amino-hydroxyethylphosphonic acids by non-aqueous capillary electrophoresis with quinine carbamate as chiral ion pair agent
  作者：Friedrich Hammerschmidt、Wolfgang Lindner、Frank Wuggenig、Elfriede Zarbl

  DOI：10.1016/s0957-4166(00)00261-5

  日期：2000.7

  Diisopropyl 2-azido-1-acetoxyethylphosphonate (+/-)-7 was hydrolysed with high enantioselectivity by lipase SP 524 to give alpha-hydroxyphosphonate (S)-(-)-6 and ester (R)-(-)-7, which was saponified to give (R)-(+)-6. The two alpha-hydroxyphosphonates (R)- and (S)-6 were transformed into 1-phosphaisoserine and L-phosphaserine, respectively. Their enantiomeric excesses were determined to be 97% by HPLC on an chiral stationary phase. A mixture of all four stereoisomeric amino-hydroxyethylphosphonic acids can be separated by non-aqueous capillary electrophoresis with quinine carbamate as the chiral ion pair agent applying the partial filling technique. (C) 2000 Elsevier Science Ltd. All rights reserved.