(S)-(-)-1-phenylethyl diethyl phosphate | 92543-26-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (S)-(-)-1-phenylethyl diethyl phosphate
• 英文别名: diethyl [(1S)-1-phenylethyl] phosphate
• CAS: 92543-26-5
• 化学式: C₁₂H₁₉O₄P
• 分子量: 258.254
• InChiKey: KEHCTXDLIGSVEI-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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：
• 作为产物：
  描述：

  phosphoric acid diethyl ester-(1-phenyl-vinyl ester) 在 Ir-chiral phosphine-oxazoline complex 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、3.0 MPa 条件下， 生成 (S)-(-)-1-phenylethyl diethyl phosphate 、 (R)-1-phenylethyl diethyl phosphate
  参考文献：
  名称：

  具有N，P配体的铱催化剂对烯醇次膦酸酯的不对称氢化。

  摘要：

  [反应：见正文]烯醇次膦酸酯是烯醇乙酸酯的结构类似物，首次被用作Ir催化的不对称氢化的底物。已经合成了许多烯醇次膦酸酯，并成功地还原了高达99％ee以上的ee。

  DOI：

  10.1021/ol070325l

文献信息

• A Simple and Convenient Synthesis of Alkyl Azides under Mild Conditions
  作者：Masato Ito、Ken-ichi Koyakumaru、Tetsuo Ohta、Hidemasa Takaya

  DOI：10.1055/s-1995-3928

  日期：1995.4

  Various primary and secondary alkyl azides have been synthesized in high yields by the fluoride anion induced SN2 substitution reactions of the corresponding alkyl halides, phosphates, or tosylates and trimethylsilyl azide.

  通过氟离子诱导的SN2取代反应，高产率合成了多种初级和次级烷基叠氮化物，反应物为相应的烷基卤化物、磷酸酯或托烷基化合物与三甲基硅基叠氮化物。
• Photochemistry of phosphate esters: an efficient method for the generation of electrophiles
  作者：Richard S. Givens、Bogdan Matuszewski、Phillip S. Athey、M. Robert Stoner

  DOI：10.1021/ja00172a016

  日期：1990.8
• Examining the origin of selectivity in the reaction of racemic alcohols with chiral N-phosphoryl oxazolidinones
  作者：Samuel Crook、Nigel J. Parr、Jonathan Simmons、Simon Jones

  DOI：10.1016/j.tetasy.2014.08.003

  日期：2014.10

  A range of known and novel N-phosphoryl oxazolidinones and imidazolidinones were prepared and screened in the kinetic resolution of a range of racemic magnesium chloroalkoxides. Models are proposed to account for the enantioselectivity achieved based on a combination of chiral relay effects, generation of transient stereochemistry and the structure of the intermediate magnesium alkoxide. (C) 2014 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/3.0/).
• Stereochemical consequences of the use of chiral N-phosphoryl oxazolidinones in the attempted kinetic resolution of bromomagnesium alkoxides
  作者：Simon Jones、Dimitrios Selitsianos

  DOI：10.1016/j.tetasy.2005.08.025

  日期：2005.9

  A number of chiral N-phosphoryl oxazolidinones have been prepared and evaluated as asymmetric phosphoryl transfer agents with the magnesium alkoxide of 1-phenyl ethanol. The reaction proceeded with little stereo selection, which was shown to be a consequence of the reaction mechanism that occurs with inversion of configuration at phosphorus consistent with in-line attack opposite the leaving group. (C) 2005 Elsevier Ltd. All rights reserved.
• 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%.