(1R)-diethyl 1-hydroxy-2-phenylethylphosphonate | 141207-36-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: (1R)-diethyl 1-hydroxy-2-phenylethylphosphonate
• 英文别名: (1R)-1-diethoxyphosphoryl-2-phenylethanol
• CAS: 141207-36-5
• 化学式: C₁₂H₁₉O₄P
• 分子量: 258.254
• InChiKey: DXONFKCUTGBFRT-GFCCVEGCSA-N

物化性质

• 沸点：
  378.6±35.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  7
• 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：

  (1R)-diethyl 1-hydroxy-2-phenylethylphosphonate 在 palladium on activated charcoal 二苯基膦叠氮化物 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 (S)-(1-Amino-2-phenylethyl)phosphonsaeure-diethylester
  参考文献：
  名称：

  Enantioselective synthesis of α-amino phosphonic acids by an application of stereoselective opening of homochiral dioxane acetals with triethyl phosphite

  摘要：

  Stereoselective opening of homochiral acetals (2a-c) with triethyl phosphite was applied to the enantioselective synthesis of phosphono alcohols (1a-c), which were successfully converted to the alpha-amino phosphonic acid diethyl esters (6a-c).

  DOI：

  10.1016/s0957-4166(00)80280-3
• 作为产物：
  描述：

  Acetic acid (R)-1-(diethoxy-phosphoryl)-2-phenyl-ethyl ester 在 三乙胺 作用下， 生成 (1R)-diethyl 1-hydroxy-2-phenylethylphosphonate
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of α-hydroxy-H-phosphinates

  摘要：

  A chiral synthesis of alpha-hydroxy-H-phosphinates was achieved via lipase-catalyzed hydrolysis of acetate precursors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.066

文献信息

• Enzymes in organic chemistry, part 2: Lipase-catalysed hydrolysis of 1-acyloxy-2-arylethylphosphonates and synthesis of phosphonic acid analogues of L-phenylalanine and L-tyrosine
  作者：Martina Drescher、Yong-Fu Li、Friedrich Hammerschmidt

  DOI：10.1016/0040-4020(95)98691-a

  日期：1995.4

  α-Hydroxyphosphonates (±)-3, prepared by base catalysed addition of phosphites 2 to aldehydes 1, were acylated to give esters (±)-4. Diethyl 1-acyloxy-2-arylethylphosphonates (±)-4a, 4b, and 4e were hydrolysed by lipase from Aspergillus niger in a biphasic system to afford (R)-α-hydroxyphosphonates of low enantiomeric purity. The corresponding diisopropyl phosphonates (±)-4c, 4f and 4g gave (S)-α-hydroxyphosphonates

  通过将亚磷酸酯2碱催化加成到醛1中而制得的α-羟基膦酸酯（±）-3被酰化，得到酯（±）-4。在双相系统中，通过来自黑曲霉的脂肪酶水解1-酰氧基-2-芳基乙基膦酸二乙酯（±）-4a，4b和4e，得到对映体纯度低的（R）-α-羟基膦酸酯。相应的二异丙基膦酸酯（±）-4c，4f和4g得到（S）-α-羟基膦酸酯，ee最高可达78％。通过其（R）-MTPA-酯的31 P NMR光谱法确定了α-羟基膦酸酯的绝对构型。化合物3a和3e分别通过其叠氮化物化学转化为L-苯丙氨酸和L-酪氨酸的膦酸类似物。
• Nonenzymatic kinetic resolution of racemic β-hydroxyalkanephosphonates with a chiral copper catalyst
  作者：Atsushi Moriyama、Shintaro Matsumura、Masami Kuriyama、Osamu Onomura

  DOI：10.1016/j.tetasy.2010.04.059

  日期：2010.4

  Kinetic resolution of beta-hydroxyalkanephosphonates was efficiently performed by 2-fluorobenzoylation in the presence of copper(II) triflate and (R,R)-Ph-BOX as a catalyst with good s value of up to 21 (C) 2010 Elsevier Ltd. All rights reserved.
• Nonenzymatic kinetic resolution of racemic α-hydroxyalkanephosphonates with chiral copper catalyst
  作者：Yosuke Demizu、Atsushi Moriyama、Osamu Onomura

  DOI：10.1016/j.tetlet.2009.07.003

  日期：2009.9

  Kinetic resolution of alpha-hydroxyalkanephosphonates was efficiently performed by benzoylation in the presence of copper(II) triflate and (R,R)-Ph-BOX as a catalyst with excellent s value of up to 286. (C) 2009 Elsevier Ltd. All rights reserved.