dimethyl (S)-(2-benzoyloxy-2-phenylethyl)phosphonate | 1239971-89-1

• 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: dimethyl (S)-(2-benzoyloxy-2-phenylethyl)phosphonate
• 英文别名: dimethyl 2-benzoyloxy-2-phenylethylphosphonate；[(1S)-2-[dimethoxy(oxido)phosphaniumyl]-1-phenylethyl] benzoate
• CAS: 1239971-89-1
• 化学式: C₁₇H₁₉O₅P
• 分子量: 334.309
• InChiKey: FIRHPBXHKURXOK-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 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：
  67.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dimethyl (Z)-2-benzoyloxy-2-phenylethenephosphonate 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 C₄₈H₄₅FeN₃P₂ 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、506.66 kPa 条件下， 反应 24.0h， 以89%的产率得到dimethyl (S)-(2-benzoyloxy-2-phenylethyl)phosphonate
  参考文献：
  名称：

  Rhodium-Catalyzed Enantioselective Hydrogenation of Unsaturated Phosphonates by ClickFerrophos Ligands

  摘要：

  Newly developed ClickFerrophos II ligands were applied in the hydrogenation of alpha,beta-unsaturated phosphonates. The use of a rhodium/ClickFerrophos II catalyst was examined in the hydrogenation of fimctionalized alpha,beta-unsaturated phosphonates and was revealed to be effective for beta-alkyl-beta-aryl or beta-dialkyl phosphonates, (Z)-beta-enolester phosphonates, and alpha-phenylethenyl phosphonates, producing the corresponding chiral phosphonates in good yields with high enantioselectivities (up to 96% ee).

  DOI：

  10.1021/jo300129m

文献信息

• Nonenzymatic kinetic resolution of racemic β-hydroxyalkanephosphonates with a chiral copper catalyst
  作者：Atsushi Moriyama、Shintaro Matsumura、Masami Kuriyama、Osamu Onomura

  DOI：10.1016/j.tetasy.2010.04.059

  日期：2010.4

  Kinetic resolution of beta-hydroxyalkanephosphonates was efficiently performed by 2-fluorobenzoylation in the presence of copper(II) triflate and (R,R)-Ph-BOX as a catalyst with good s value of up to 21 (C) 2010 Elsevier Ltd. All rights reserved.
• Rhodium-Catalyzed Enantioselective Hydrogenation of Unsaturated Phosphonates by ClickFerrophos Ligands
  作者：Takashi Konno、Kenta Shimizu、Kenichi Ogata、Shin-ichi Fukuzawa

  DOI：10.1021/jo300129m

  日期：2012.4.6

  Newly developed ClickFerrophos II ligands were applied in the hydrogenation of alpha,beta-unsaturated phosphonates. The use of a rhodium/ClickFerrophos II catalyst was examined in the hydrogenation of fimctionalized alpha,beta-unsaturated phosphonates and was revealed to be effective for beta-alkyl-beta-aryl or beta-dialkyl phosphonates, (Z)-beta-enolester phosphonates, and alpha-phenylethenyl phosphonates, producing the corresponding chiral phosphonates in good yields with high enantioselectivities (up to 96% ee).