diethyl 4-(1-hydroxyethyl)phenylphosphonate | 61737-89-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl 4-(1-hydroxyethyl)phenylphosphonate
• 英文别名: 1-(4-Diethoxyphosphorylphenyl)ethanol
• CAS: 61737-89-1
• 化学式: C₁₂H₁₉O₄P
• 分子量: 258.254
• InChiKey: IMYPVTMAZUTNPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  diethyl 4-(1-hydroxyethyl)phenylphosphonate 在 potassium hydrogensulfate 作用下， 生成 4-vinylbenzenephosphonic acid diethyl ester
  参考文献：
  名称：

  带有膦酸酯吸电子基团的新的NLO二苯乙烯衍生物

  摘要：

  描述了带有膦酸酯作为吸电子官能团的新型电子供体-受体取代的对苯二甲酸酯的合成和表征。芳香环的磷酸化是通过Ni催化的Arbuzov反应完成的，而Pd催化的Heck型偶联反应则被用于构建二苯乙烯衍生物。通过确定电光系数（r 33），证明了膦酸酯基作为基于的二阶NLO材料的吸电子基团是有效的。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4039(97)01390-7
• 作为产物：
  描述：

  在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 diethyl 4-(1-hydroxyethyl)phenylphosphonate
  参考文献：
  名称：

  Application of a promiscuous Arthrobacter sp. from Antarctic in aerobic (R)-selective deracemization and anaerobic (S)-selective reduction

  摘要：

  Inspired by enzyme-catalyzed reactions with microorganisms found in harsh marine environments, in which the amount of oxygen is restrict, we have shown that Arthrobacter sp. can perform different chemical transformations by switching from anaerobic to aerobic reaction conditions. Depending on the presence or absence of oxygen, either alcohol deracemization or ketone reduction with enantiocomplementary selectivities can be performed by the same microorganism. For example, reactions performed in the presence of oxygen favored the deracemization process, in which a racemic mixture of 1-(4-methylphenyl) ethanol was enriched to the (R)-alcohol in high conversion (94%) and high enantiomeric excess (94%). On the other hand, reaction in the absence of oxygen favored the reduction process, in which 4-methyl-acetophenone was converted to the (S)-alcohol in good conversion (58%) and excellent enantiomeric excess (> 99%). These concepts were applied for both deracemization and enantio selective reduction of heteroatom-containing (silicon, phosphorus, tin and boron) molecules. Moreover, preparative scale reactions were also performed for both chemical processes. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.09.016