[(1R)-1-[oxido-di(propan-2-yloxy)phosphaniumyl]ethyl] acetate | 189387-00-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: [(1R)-1-[oxido-di(propan-2-yloxy)phosphaniumyl]ethyl] acetate
• CAS: 189387-00-6
• 化学式: C₁₀H₂₁O₅P
• 分子量: 252.247
• InChiKey: PZQOBQGCYQRAKP-SNVBAGLBSA-N

物化性质

• 沸点：
  304.1±25.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(1R)-1-[oxido-di(propan-2-yloxy)phosphaniumyl]ethyl] acetate 在 甲醇 、 偶氮二甲酸二叔丁酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-(+)-diisopropyl 1-(phthalimidooxy)ethylphosphonate
  参考文献：
  名称：

  Enzymes in organic chemistry — 5: First and chemo-enzymatic synthesis of α-aminooxyphosphonic acids of high enantiomeric excess

  摘要：

  alpha-Acyloxyphosphonates (+/-)-5a and (+/-)-5b, derived from 3-phenylpropionaldehyde and acetaldehyde. were involved by lipase-catalyzed enantioselective hydrolysis. Three of the four chiral, non-racemic alpha-hydroxyphosphonates obtained had 99% ee. the fourth 91%. They were transformed chemically into alpha-aminooxyphosphonic acids. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00174-9
• 作为产物：
  描述：

  diisopropyl 1-hydroxyethylphosphonate 在 lipase SP 524 吡啶 、 sodium hydroxide 、 phosphate buffer 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 26.0h， 生成 [(1R)-1-[oxido-di(propan-2-yloxy)phosphaniumyl]ethyl] acetate
  参考文献：
  名称：

  Enzymes in organic chemistry — 5: First and chemo-enzymatic synthesis of α-aminooxyphosphonic acids of high enantiomeric excess

  摘要：

  alpha-Acyloxyphosphonates (+/-)-5a and (+/-)-5b, derived from 3-phenylpropionaldehyde and acetaldehyde. were involved by lipase-catalyzed enantioselective hydrolysis. Three of the four chiral, non-racemic alpha-hydroxyphosphonates obtained had 99% ee. the fourth 91%. They were transformed chemically into alpha-aminooxyphosphonic acids. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00174-9

文献信息

• Enzymes in Organic Chemistry, 11:[1] Hydrolase-Catalyzed Resolution ofα- andβ-Hydroxyphosphonates and Synthesis of Chiral, Non-Racemicβ-Aminophosphonic Acids
  作者：A. Woschek、Wolfgang Lindner、F. Hammerschmidt

  DOI：10.1002/adsc.200303135

  日期：2003.12

  enantioselective acylation of racemic diisopropyl α- and β-hydroxyphosphonates by hydrolases in t-butyl methyl ether with isopropenyl acetate as acyl donor is limited by the narrow substrate specificity of the enzymes. High enantiomeric excesses (up to 99%) were obtained for the acetates of (S)-diisopropyl 1-hydroxy-(2-thienyl)methyl-, 1-hydroxyethyl- and 1-hydroxyhexylphosphonate and (R)-diisopropyl 2-hydroxypropylphosphonate

  外消旋二异丙基α-和β-羟基膦酸酯在叔丁基甲基醚中通过水解酶与乙酸异丙烯酯作为酰基供体的对映选择性酰化受到酶狭窄的底物特异性的限制。对于（S）-二异丙基1-羟基-（2-噻吩基）甲基-，1-羟乙基-和1-羟己基膦酸酯和（R）-二异丙基2-羟丙基膦酸酯的乙酸酯，获得高对映体过量（至多99％）。双相系统中念珠菌和蛋白酶枯草杆菌蛋白酶对脂肪酶水解多种β-氯乙酰氧基膦酸酯的作用是对映体选择性的（S）-β-羟基膦酸酯（ee 51–92％）。（S）-2-苯基-2-羟乙基-和（S）-3-甲基-2-羟基丁基膦酸酯（ee分别为96％和99％）被转化为相同ee的（R）-2-氨基膦酸。
• Synthesis of a novel ruthenium(ІІ) complex and its unique behaviors in enzymatic dynamic kinetic resolution of secondary alcohols
  作者：Qihui Chen、Chengye Yuan

  DOI：10.1016/j.tet.2010.03.069

  日期：2010.5

  was first prepared as an efficient catalyst in Candida Antarctica lipase B (CALB) mediated dynamic kinetic resolution (DKR) of secondary alcohols. With the aid of this ruthenium complex 3, (S)-1-phenylethanol was completely racemized within 25 min, and in combination with CALB, series of secondary alcohols bearing various functional groups were resolved in an efficient DKR manner. A detailed mechanism

  首先制备了环戊二烯基苯甲酰基钌（ІІ）配合物3作为南迪假丝酵母脂肪酶B（CALB）介导的仲醇动力学动力学拆分（DKR）的有效催化剂。借助于该钌配合物3，（S）-1-苯基乙醇在25分钟内完全消旋，并与CALB结合，以有效的DKR方式拆分了一系列带有各种官能团的仲醇。提出了涉及C–H键激活的详细机制，以形成复合物3通过捕获此途径中的关键中间体。进行了相关的机理研究，以说明这种类型的DKR催化剂是基于仲醇的外消旋作用。其结构的新颖性，独特的催化性能以及在各种底物上的广泛应用以及更高的效率，使络合物3成为了DKR工艺中常用的那些络合物的重要替代品。