1-benzoyloxy-1-dimethylphosphonyl-2-(4-fluorophenyl)ethane | 1011482-42-0

• 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: 1-benzoyloxy-1-dimethylphosphonyl-2-(4-fluorophenyl)ethane
• 英文别名: [1-Dimethoxyphosphoryl-2-(4-fluorophenyl)ethyl] benzoate
• CAS: 1011482-42-0；960128-85-2
• 化学式: C₁₇H₁₈FO₅P
• 分子量: 352.299
• InChiKey: VLWPCJPZXWWEMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (E)-1-benzoyloxy-1-dimethoxyphosphoryl-2-(4-fluorophenyl)ethene 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、1.01 MPa 条件下， 反应 24.0h， 以99%的产率得到1-benzoyloxy-1-dimethylphosphonyl-2-(4-fluorophenyl)ethane
  参考文献：
  名称：

  Readily Available Chiral Phosphine−Aminophosphine Ligands for Highly Efficient Rh-Catalyzed Asymmetric Hydrogenation of α-Enol Ester Phosphonates and α-Enamido Phosphonates

  摘要：

  [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.

  DOI：

  10.1021/jo702488j

文献信息

• Modular Phosphine-Aminophosphine Ligands Based on Chiral 1,2,3,4-Tetrahydro-1-naphthylamine Backbone: A New Class of Practical Ligands for Enantioselective Hydrogenations
  作者：Min Qiu、Xiang-Ping Hu、Jia-Di Huang、Dao-Yong Wang、Jun Deng、Sai-Bo Yu、Zheng-Chao Duan、Zhuo Zheng

  DOI：10.1002/adsc.200800418

  日期：——

  been achieved in the hydrogenation of most substrates tested, demonstrating the high potential of these newly developed phosphine-aminophosphine ligands in asymmetric catalysis. The present research also discloses that these newly developed phosphine-aminophosphine ligands are more efficient than that derived from (S)-1-phenylethylamine, suggesting that the increased rigidity conferred by a cyclohexyl

  （R）-1,2,3,4-四氢-1-萘胺经两步法制备了一系列新的手性膦-氨基膦配体[（R）-HW-Phos] ，并成功应用于铑催化的各种官能化烯烃的不对称加氢反应，例如α-烯醇酯膦酸酯，α-烯酰胺膦酸酯，（Z）-β-（酰氨基）丙烯酸酯等。在大多数受试底物的氢化反应中，均具有出色的对映选择性，这表明这些新开发的膦-氨基膦配体在不对称催化中具有很高的潜力。本研究还公开了这些新开发的膦-氨基膦配体比衍生自（S）-1-苯基乙胺，表明在这些膦-氨基膦配体中由环己基片段赋予的增加的刚性在不对称诱导中具有积极作用。
• 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.