diethyl 1-butyryloxy-1-phenylmethanephosphonate | 667915-47-1

• 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 1-butyryloxy-1-phenylmethanephosphonate
• 英文别名: diethyl n-butyryloxy(phenyl)methane phosphonate
• CAS: 667915-47-1
• 化学式: C₁₅H₂₃O₅P
• 分子量: 314.318
• InChiKey: HSCKMFXYXIWTLX-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  苯甲醛 在 aluminum oxide 、 potassium fluoride 、 lipase from Candida cylindracea 作用下， 以 异丙醚 为溶剂， 反应 180.0h， 生成 diethyl 1-butyryloxy-1-phenylmethanephosphonate 、 diethyl [(S)-hydroxy(phenyl)methyl]phosphonate 、 diethyl [(R)-hydroxy(phenyl)methyl]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

文献信息

• Whole-cell biotransformation of diethyl 1-hydroxy-1-phenylmethanephosphonate in a different reaction environment
  作者：Paulina Majewska

  DOI：10.1080/10426507.2016.1247088

  日期：2017.4.3

  properties, was tested as well as nutrient broth medium. The enantioselectivity of the hydrolysis reactions was at the same level (50% conversion, ∼80% ee) regardless of the used medium, but the time of reaction varied significantly, depending on the medium in which the microorganism was grown and on the reaction medium. The addition of 0.01% of tributyrin shortened the response time in the range from 30

  图形摘要摘要外消旋1-丁酰氧基-1-苯基甲烷-膦酸酯的对映异构体的全细胞生物催化拆分由枯草芽孢杆菌菌株在不同培养基中进行。为此，测试了众所周知的诱导脂肪分解特性的培养基以及营养肉汤培养基。无论使用何种培养基，水解反应的对映选择性都处于相同水平（50% 转化率，~80% ee），但反应时间差异很大，这取决于微生物生长的培养基和反应培养基. 添加 0.01% 的三丁酸甘油酯将响应时间从 30 分钟缩短到 1 小时。此外，当含有三丁酸甘油酯的营养肉汤用作生长和生物转化反应的培养基时，对映选择性也从 23 增加到 35。