Phosphoric acid 2-phenylethyl dimethyl ester | 94626-26-3

• 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: Phosphoric acid 2-phenylethyl dimethyl ester
• 英文别名: dimethyl 2-phenylethyl phosphate；dimethyl (3-phenylethyl) phosphate；Dimethyl-phenethyl-phosphat；phosphoric acid dimethyl ester-phenethyl ester；Phosphorsaeure-dimethylester-phenaethylester
• CAS: 94626-26-3
• 化学式: C₁₀H₁₅O₄P
• 分子量: 230.2
• InChiKey: XEAPATVNFBFXHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  Phosphoric acid 2-phenylethyl dimethyl ester 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 2-Phenylethyl phosphate
  参考文献：
  名称：

  A Mild Preparation of Protected Phosphate Esters From Alcohols

  摘要：

  Treatment of a wide variety of alcohols with trimethyl phosphite and carbon tetrabromide in pyridine leads to the formation of the corresponding dimethyl phosphate esters in high yields. The reaction is presumed to proceed by formation of an intermediate alkoxy trimethoxyphosphonium salt which undergoes selective demethylation by bromide. Poor yields are generally obtained if solvents other than pyridine are employed or if carbon tetrabromide is replaced by carbon tetrachloride. The mildness of the procedure is illustrated by the conversion of the highly acid sensitive 2-(4,4'-dimethoxytrityloxy)-1-phenylethanol to its dimethyl phosphate ester (74%) and the base sensitive N-CBZ-tyrosine-p-nitrophenyl ester to the corresponding O-(dimethyl phosphate ester) (82%). The availability of methods for the demethylation of methyl phosphate esters makes this oxidative phosphorylation reaction a mild and inexpensive method for the synthesis of protected phosphate esters.

  DOI：

  10.1021/jo00117a018
• 作为产物：
  描述：

  苯乙醇 、 氯磷酸二甲酯 在 吡啶 作用下， 生成 Phosphoric acid 2-phenylethyl dimethyl ester
  参考文献：
  名称：

  Cheymol et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 247, p. 1014

  摘要：

  DOI：

文献信息

• Visible-Light-Mediated Access to Phosphate Esters
  作者：Alya Inial、Fabrice Morlet-Savary、Jacques Lalevée、Annie−Claude Gaumont、Sami Lakhdar

  DOI：10.1021/acs.orglett.0c01409

  日期：2020.6.5

  We report herein a practically simple visible-light photocatalytic approach for the synthesis of a large variety of phosphate esters through the combination of N-alkoxypyridinium salts and phosphites under mild conditions. The scope of the reaction is broad and the protocol was successfully applied to the synthesis of biologically relevant structures. Quantum yield measurements, as well as EPR experiments

  我们在此报告了在温和条件下通过N-烷氧基吡啶鎓盐和亚磷酸酯的组合合成多种磷酸酯的一种实用的可见光光催化方法。反应的范围很广，该方案已成功地应用于生物学相关结构的合成。量子产率的测量以及EPR实验，提示了合理的反应机理。
• Isopropenyl phosphate as an atom efficient reagent for phosphorylation of alcohols with catalytic base
  作者：Jens Wéry、Igor Beckers、Dirk E. De Vos

  DOI：10.1039/d3ra02293e

  日期：——

  The atom efficient transesterification of phosphate esters with catalytic base was investigated using an isopropenyl leaving group, generating acetone as the only by-product. The reaction proceeds in good yields at room temperature, with excellent chemoselectivity towards primary alcohols. Mechanistic insights were obtained by obtaining kinetic data using in operando NMR-spectroscopy.

  使用异丙烯基离去基团研究了磷酸酯与催化碱的原子高效酯交换反应，产生丙酮作为唯一的副产物。该反应在室温下以良好的收率进行，对伯醇具有出色的化学选择性。通过使用原位核磁共振波谱法获得动力学数据，获得了机理见解。
• 1,3-Dimethyl-2-(3-nitro-1,2,4-triazol-1-yl)-2-pyrrolidin-1-yl-1,3,2-diazaphospholidinium hexafluorophosphate (MNTP): a powerful condensing reagent for phosphate and phosphonate esters
  作者：Natsuhisa Oka、Mamoru Shimizu、Kazuhiko Saigo、Takeshi Wada

  DOI：10.1016/j.tet.2006.01.084

  日期：2006.4

  A novel phosphonium-type condensing reagent, 1,3-dimethyl-2-(3-nitro-1,2,4-triazol-1-yl)-2-pyrrolidin-1-yl-1,3,2-diazaphospholidinium hexafluorophosphate (MNTP), was designed and synthesized. A P-31 NMR study oil the condensation reactions of phosphate, alkylphosphonate , boranophosphate, and H-phosphonate derivatives with an alcohol in the presence of MNTP demonstrated the versatility and the enhanced activity of the new condensing reagent, compared to the previously reported phosphonium-type condensing reagents. The mechanism of the condensation reactions mediated by MNTP is discussed on the basis of the P-31 NMR studies and theoretical calculations. (c) 2006 Elsevier Ltd. All rights, reserved.
• POLYNUCLEOTIDE CONSTRUCTS HAVING BIOREVERSIBLE AND NON-BIOREVERSIBLE GROUPS
  申请人：BRADSHAW Curt W.

  公开号：US20170114341A1

  公开（公告）日：2017-04-27

  The invention features a hybridized polynucleotide construct containing a passenger strand, a guide strand loadable into a RISC complex, and (i) a 3′-terminal or an internucleotide non-bioreversible group in the guide strand; or (ii) a 5′-terminal, a 3′-terminal, or an internucleotide non-bioreversible group in the passenger strand, and a 5′-terminal, a 3′-terminal, or an internucleotide disulfide bioreversible group in the guide strand or the passenger strand. The invention also features methods of delivering a polynucleotide to a cell using the hybridized polynucleotide construct. The invention further features methods of reducing the expression of a polypeptide in a cell using the hybridized polynucleotide construct.
• Cheymol et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 247, p. 1014
  作者：Cheymol et al.

  DOI：——

  日期：——