(S)-(+)-1-benzoyloxy-1-dimethylphosphonylpropane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(+)-1-benzoyloxy-1-dimethylphosphonylpropane
• 英文别名: (S)-1-(dimethoxyphosphoryl)propyl benzoate；[(1S)-1-dimethoxyphosphorylpropyl] benzoate
• 化学式: C₁₂H₁₇O₅P
• 分子量: 272.238
• InChiKey: UJTDHHNYLZPNMT-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dimethyl 1-oxopropylphosphonate 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 C₃₆H₃₂N₃O₃P 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 (S)-(+)-1-benzoyloxy-1-dimethylphosphonylpropane
  参考文献：
  名称：

  单齿亚磷酰胺 的Rh（i）配合物催化α-或β-酰氧基α，β-不饱和膦酸酯的不对称氢化† ‡

  摘要：

  已经公开了带有伯胺部分（DpenPhos）的单齿亚磷酰胺的Rh（I）配合物对于多种α-或β-酰氧基α，β-不饱和膦酸酯的不对称氢化非常有效，从而提供了相应的生物学作用。重要的具有出色对映选择性（90-> 99％ee）的手性α-或β-羟基膦酸衍生物。

  DOI：

  10.1039/c1ob06835k

文献信息

• Asymmetric Hydrogenation of Enamides, α-Enol and α-Enamido Ester Phosphonates Catalyzed by IndolPhos-Rh Complexes
  作者：Jeroen Wassenaar、Joost N. H. Reek

  DOI：10.1021/jo9018683

  日期：2009.11.6

  The scope of the IndolPhos-Rh-catalyzed asymmetric hydrogenation of enamides, alpha-enol and alpha-enamido ester phosphonates, hits been investigated. In addition, Taddol-based IndolPhos ligands are introduced. High activities and good to excellent enantioselectivities up to 99% ee are obtained fora broad range of structurally diverse substrates, giving important chiral products such as alpha, beta(2), and beta(3) amino acid derivatives, arylamines, and amino and hydroxy phosphonates.
• Enantioselective Synthesis of α-Hydroxy and α-Amino Phosphonates via Catalytic Asymmetric Hydrogenation
  作者：Mark J. Burk、Timothy A. Stammers、Judith A. Straub

  DOI：10.1021/ol9906099

  日期：1999.8.1

  [GRAPHICS]Cationic rhodium catalysts of the C-2 symmetric DuPHOS (1) and BPE (2) ligands have demonstrated the ability to asymmetrically hydrogenate a novel series of enol phosphonates (3) in good to excellent enantiomeric excess under mild conditions. Initial studies toward the catalytic asymmetric hydrogenation of enamido phosphonates (6 and 7) using the DuPHOS-Rh+ catalysts are also reported.
• Readily Available Chiral Phosphine−Aminophosphine Ligands for Highly Efficient Rh-Catalyzed Asymmetric Hydrogenation of α-Enol Ester Phosphonates and α-Enamido Phosphonates
  作者：Dao-Yong Wang、Jia-Di Huang、Xiang-Ping Hu、Jun Deng、Sai-Bo Yu、Zheng-Chao Duan、Zhuo Zheng

  DOI：10.1021/jo702488j

  日期：2008.3.1

  [GRAPHICS]A new class of unsymmetrical hybrid phosphine-aminophosphine ligands has been prepared from commercially available, inexpensive (S)-1-phenylethylamine through a concise synthetic procedure. These ligands are not very sensitive to air and moisture, and displayed good enantioselectivities in the Rh-catalyzed asymmetric hydrogenation of various dimethyl alpha-benzoyloxyethenephosphonates bearing beta-aryl, beta-alkyl, and beta-alkoxy substituents and N-benzyloxycarbonyl alpha-enamido phosphonates, in which up to 97% ee was obtained. A side-by-side comparison study disclosed that these new phosphine-aminophosphine ligands showed better enantioselectivity than BoPhoz ligands.
• Asymmetric hydrogenation of α- or β-acyloxy α,β-unsaturated phosphonates catalyzed by a Rh(i) complex of monodentate phosphoramidite
  作者：Jinzhu Zhang、Kaiwu Dong、Zheng Wang、Kuiling Ding

  DOI：10.1039/c1ob06835k

  日期：——

  The Rh(I) complex of a monodentate phosphoramidite bearing a primary amine moiety (DpenPhos) has been disclosed to be highly efficient for the asymmetric hydrogenation of a variety of α- or β-acyloxy α,β-unsaturated phosphonates, providing the corresponding biologically important chiral α- or β-hydroxy phosphonic acid derivatives with excellent enantioselectivities (90–>99% ee).

  已经公开了带有伯胺部分（DpenPhos）的单齿亚磷酰胺的Rh（I）配合物对于多种α-或β-酰氧基α，β-不饱和膦酸酯的不对称氢化非常有效，从而提供了相应的生物学作用。重要的具有出色对映选择性（90-> 99％ee）的手性α-或β-羟基膦酸衍生物。