(R)-(+)-(1-Hydroxy-1-phenylethyl)phosphonsaeurediethylester | 104549-97-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (R)-(+)-(1-Hydroxy-1-phenylethyl)phosphonsaeurediethylester
• 英文别名: (1R)-1-diethoxyphosphoryl-1-phenylethanol
• CAS: 104549-97-5
• 化学式: C₁₂H₁₉O₄P
• 分子量: 258.254
• InChiKey: XAOWLBAJYUPADQ-GFCCVEGCSA-N

物化性质

• 沸点：
  373.6±35.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

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：

  (R)-(+)-(1-Hydroxy-1-phenylethyl)phosphonsaeurediethylester 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 反应 120.0h， 以27%的产率得到diethyl (1-phenylethyl) phosphate
  参考文献：
  名称：

  Die Phosphonat-Phosphat- und Phosphat-Phosphonat-Umlagerung und ihre Anwendung, Teil 2: Stereochemie der Phosphonat-Phosphat-Umlagerung am Kohlenstoff am Beispiel der Isomerisierung von (R)-(+)- und (S)-(?)-(1-Hydroxy-1-phenylethyl)-phosphons�ure-diethylester

  摘要：

  The phosphonate-phosphate-rearrangement of (R)-(+)- and (S)-(-)-6 was investigated at room temperature in various organic solvents and mixtures of organic solvent and of up to 7% of water, using potassium t-butoxide, potassium hydroxide, and DBU as bases. The rearrangement is shown to occur with retention of configuration at carbon. The highest enantiomeric excess (10.7%) for phosphate 8 was observed using a mixture of DMSO and water (100:7) containing DBU as base. Under these conditions the cleavage of phosphonate 6 into acetophenone and phosphite predominates and the yield of phosphate 8 is only 7.7%.

  DOI：

  10.1007/bf00814152
• 作为产物：
  描述：

  (S)-(-)-1-phenylethyl diethyl phosphate 在 正丁基锂 、 正己烷 、 二异丙胺 作用下， 以 甲苯 为溶剂， 以81%的产率得到(R)-(+)-(1-Hydroxy-1-phenylethyl)phosphonsaeurediethylester
  参考文献：
  名称：

  Hammerschmidt, Friedrich; Voellenkle, Horst, Liebigs Annalen der Chemie, 1986, # 12, p. 2053 - 2064

  摘要：

  DOI：

文献信息

• HAMMERSCHMIDT F.; VOLLENKLE H., LIEBIDS ANN. CHEM.,(1986) N 12, 2053-2064
  作者：HAMMERSCHMIDT F.、 VOLLENKLE H.

  DOI：——

  日期：——
• Hammerschmidt, Friedrich; Voellenkle, Horst, Liebigs Annalen der Chemie, 1986, # 12, p. 2053 - 2064
  作者：Hammerschmidt, Friedrich、Voellenkle, Horst

  DOI：——

  日期：——
• Die Phosphonat-Phosphat- und Phosphat-Phosphonat-Umlagerung und ihre Anwendung, Teil 2: Stereochemie der Phosphonat-Phosphat-Umlagerung am Kohlenstoff am Beispiel der Isomerisierung von (R)-(+)- und (S)-(?)-(1-Hydroxy-1-phenylethyl)-phosphons�ure-diethylester
  作者：F. Hammerschmidt

  DOI：10.1007/bf00814152

  日期：1993.10

  The phosphonate-phosphate-rearrangement of (R)-(+)- and (S)-(-)-6 was investigated at room temperature in various organic solvents and mixtures of organic solvent and of up to 7% of water, using potassium t-butoxide, potassium hydroxide, and DBU as bases. The rearrangement is shown to occur with retention of configuration at carbon. The highest enantiomeric excess (10.7%) for phosphate 8 was observed using a mixture of DMSO and water (100:7) containing DBU as base. Under these conditions the cleavage of phosphonate 6 into acetophenone and phosphite predominates and the yield of phosphate 8 is only 7.7%.