dibenzyl n-butyryloxy(phenyl)methane phosphonate | 1378313-91-7

• 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: dibenzyl n-butyryloxy(phenyl)methane phosphonate
• CAS: 1378313-91-7
• 化学式: C₂₅H₂₇O₅P
• 分子量: 438.46
• InChiKey: SJINCNRIDCUCKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dibenzyl n-butyryloxy(phenyl)methane phosphonate 在 lipase from Pseudomonas fluorescens 作用下， 以 正己烷 、 异丙醚 为溶剂， 反应 168.0h， 生成 (S)-dibenzyl [hydroxy(phenyl)methyl]phosphonate 、 dibenzyl n-butyryloxy(phenyl)methane phosphonate 、 dibenzyl n-butyryloxy(phenyl)methane phosphonate 、 Phosphonic acid, (hydroxyphenylmethyl)-, bis(phenylmethyl) ester, (R)-
  参考文献：
  名称：

  Kinetic resolution of (±)-diethyl- and dibenzyl hydroxy(phenyl)methanephosphonates and their acyl derivatives with lipases

  摘要：

  A wide variety of commercially available lipases and microbial whole cells were tested for biotransformations of (+/-)-diethyl and dibenzyl hydroxyl(phenyl) methanephosphonates. Biocatalytic hydrolysis of acylated hydroxyphosphonates by whole cells of Bacillus subtilis gave optically active compounds with 95% ee (S). Enantioselectivities obtained when using commercially available enzymatic preparations were less satisfactory, leading to both compounds with an enantiomeric excess in the range 15-35%. Screening lipases for their ability to acylate these phosphonates or to hydrolyze their acylated derivatives enabled selection of enzymes and organisms suitable for use in both processes.

  DOI：

  10.3109/10242422.2011.631211
• 作为产物：
  描述：

  苯甲醛 在 aluminum oxide 、 potassium fluoride 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 20.0h， 生成 dibenzyl n-butyryloxy(phenyl)methane phosphonate
  参考文献：
  名称：

  Kinetic resolution of (±)-diethyl- and dibenzyl hydroxy(phenyl)methanephosphonates and their acyl derivatives with lipases

  摘要：

  A wide variety of commercially available lipases and microbial whole cells were tested for biotransformations of (+/-)-diethyl and dibenzyl hydroxyl(phenyl) methanephosphonates. Biocatalytic hydrolysis of acylated hydroxyphosphonates by whole cells of Bacillus subtilis gave optically active compounds with 95% ee (S). Enantioselectivities obtained when using commercially available enzymatic preparations were less satisfactory, leading to both compounds with an enantiomeric excess in the range 15-35%. Screening lipases for their ability to acylate these phosphonates or to hydrolyze their acylated derivatives enabled selection of enzymes and organisms suitable for use in both processes.

  DOI：

  10.3109/10242422.2011.631211