dimethyl 2-oxo-2-(3,4,5-trimethoxyphenyl)ethylphosphonate | 1161444-37-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 2-oxo-2-(3,4,5-trimethoxyphenyl)ethylphosphonate
• 英文别名: 2-[Dimethoxy(oxido)phosphaniumyl]-1-(3,4,5-trimethoxyphenyl)ethanone；2-[dimethoxy(oxido)phosphaniumyl]-1-(3,4,5-trimethoxyphenyl)ethanone
• CAS: 1161444-37-6
• 化学式: C₁₃H₁₉O₇P
• 分子量: 318.263
• InChiKey: SPYTUQJWXSCHLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  86.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 2-oxo-2-(3,4,5-trimethoxyphenyl)ethylphosphonate 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 C₃₇H₃₅FeN₂P 、 potassium tert-butylate 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、2.0 MPa 条件下， 反应 24.0h， 以92%的产率得到dimethyl (R)-(2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl)phosphonate
  参考文献：
  名称：

  铱催化β-酮膦酸酯与手性二茂铁基P,N,N-配体的不对称氢化

  摘要：

  β-酮膦酸酯与手性 Ir/P,N,N-配体催化剂的不对称氢化已被开发。一系列β-酮膦酸酯被氢化，在温和的条件下以高收率获得了相应的β-羟基膦酸酯，具有良好或优异的对映选择性。

  DOI：

  10.1002/aoc.6283
• 作为产物：
  描述：

  dimethyl 2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethylphosphonate 在 potassium permanganate 作用下， 以 苯 为溶剂， 反应 13.0h， 以65%的产率得到dimethyl 2-oxo-2-(3,4,5-trimethoxyphenyl)ethylphosphonate
  参考文献：
  名称：

  Synthesis of β-ketophosphonates with electron rich β-aryl groups as useful organophosphorus reagents in lignans synthesis

  摘要：

  Investigation of the oxidation reaction of election rich alkoxy substituted beta-aryl beta-hydroxyphosphonates to Corresponding beta-ketophosphonates. which may be Utilized in syntheses of lignans with various oxidizing agents (PCC, PDC, SIBX, CAN, Oxone (R), KMNO4,SiO2, KMNO4/MS 4 angstrom, KMNO4/CuSO4, KMNO4/CuSO4 Al2O3, MnO2, CrO3/SiO2, H2O2/salen) is described. The effect of oxidants and reaction conditions on the reaction efficiency and yield was also investigated. (C) 2009 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tet.2009.03.025

文献信息

• Synthesis of β-ketophosphonates with electron rich β-aryl groups as useful organophosphorus reagents in lignans synthesis
  作者：Marek Koprowski、Dorota Szymańska、Agnieszka Bodzioch、Bernard Marciniak、Ewa Różycka-Sokołowska、Piotr Bałczewski

  DOI：10.1016/j.tet.2009.03.025

  日期：2009.5

  Investigation of the oxidation reaction of election rich alkoxy substituted beta-aryl beta-hydroxyphosphonates to Corresponding beta-ketophosphonates. which may be Utilized in syntheses of lignans with various oxidizing agents (PCC, PDC, SIBX, CAN, Oxone (R), KMNO4,SiO2, KMNO4/MS 4 angstrom, KMNO4/CuSO4, KMNO4/CuSO4 Al2O3, MnO2, CrO3/SiO2, H2O2/salen) is described. The effect of oxidants and reaction conditions on the reaction efficiency and yield was also investigated. (C) 2009 Elsevier Ltd. All rights reserved,
• Iridium‐catalyzed asymmetric hydrogenation of β‐ketophosphonates with chiral ferrocenyl P,N,N‐ligands
  作者：Yin‐Feng Ma、Chuan‐Jin Hou、De‐Quan Wei、Xinwei He、Ting‐Ting Chu、Xiu‐shuai Chen、Xiang‐Ping Hu

  DOI：10.1002/aoc.6283

  日期：2021.8

  The asymmetric hydrogenation of β-ketophosphonates with chiral Ir/P,N,N-ligands catalyst has been developed. A series of β-ketophosphonates were hydrogenated, and the corresponding β-hydroxyphosphonates were obtained in high yields with good or excellent enantioselectivities under mild condition.

  β-酮膦酸酯与手性 Ir/P,N,N-配体催化剂的不对称氢化已被开发。一系列β-酮膦酸酯被氢化，在温和的条件下以高收率获得了相应的β-羟基膦酸酯，具有良好或优异的对映选择性。