diethyl 2-oxo-2-(2'-pyridyl)ethanephosphonate | 103687-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl 2-oxo-2-(2'-pyridyl)ethanephosphonate
• 英文别名: le 2(-pyridyl)-2 oxo-2 ethylphosphonate de diethyle；diethyl (2-oxo-2-(pyridin-2-yl)ethyl)phosphonate；Phosphonic acid, [2-oxo-2-(2-pyridinyl)ethyl]-, diethyl ester；2-diethoxyphosphoryl-1-pyridin-2-ylethanone
• CAS: 103687-20-3
• 化学式: C₁₁H₁₆NO₄P
• 分子量: 257.226
• InChiKey: KTOKAXBSNRGBSX-UHFFFAOYSA-N

物化性质

• 沸点：
  382.0±22.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-oxo-2-(2'-pyridyl)ethanephosphonate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以95%的产率得到diethyl 2-hydroxy-2-(2'-pyridyl)ethanephosphonate
  参考文献：
  名称：

  Biocatalytic syntheses of chiral non-racemic 2-hydroxyalkanephosphonates

  摘要：

  A series of 2-oxoalkanephosphonates 2 were screened for reduction with Geotrichum candidum. Only diethyl 2-oxopropanephosphonate 2a underwent asymmetric reduction to give (+)-(R)-diethyl 2-hydroxypropanephosphonate 3a with 98% e.e. In turn, a series of racemic 2-hydroxyalkanephosphonates 3 were acetylated under kinetic resolution conditions in the presence of various lipases to give the corresponding 2-acetoxyalkanephosphonates 4 and recovered alcohols 3 in good yields and with e.e. up to 93%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00567-5
• 作为产物：
  描述：

  2-乙炔基吡啶 、 亚磷酸二乙酯 在 iron(III) chloride 、 氧气 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以39%的产率得到diethyl 2-oxo-2-(2'-pyridyl)ethanephosphonate
  参考文献：
  名称：

  β-Ketophosphonate Formation via Aerobic Oxyphosphorylation of Alkynes or Alkynyl Carboxylic Acids with H-Phosphonates

  摘要：

  A synergistic Cu/Fe-catalyzed aerobic oxyphosphorylation of alkynes or alkynyl carboxylic acids with H-phosphonate is disclosed. The useful beta-ketophosphonate products were obtained in good yields under oxygen atmosphere in a novel way. This reaction exhibits a wide substrate scope, and the mechanistic experiments indicate that a radical mechanism forms both C-P and C=O bonds simultaneously. This mechanism contrasts existing aerobic difunctionalization of alkynes.

  DOI：

  10.1021/acs.orglett.5b00574

文献信息

• Novel Cobalt(0)- or Magnesium-Mediated Approaches to β-Ketophosphonates
  作者：Fulvia Orsini、Emanuela Di Teodoro、Marinella Ferrari

  DOI：10.1055/s-2002-33653

  日期：——

  Two novel approaches to β-ketophosphonates, based on cobalt(0)- or magnesium-mediated reactions of α-halophosphonates with esters are described.

  描述了两种新颖的方法，通过钴(0)或镁介导的反应，将α-卤化膦酸酯与酯反应，得到β-酮膦酸酯。
• Aboujaoude, Elie Elia; Collignon, Noel; Teulade, Marie-Paule, Phosphorus and Sulfur and the Related Elements, 1985, vol. 25, p. 57 - 62
  作者：Aboujaoude, Elie Elia、Collignon, Noel、Teulade, Marie-Paule、Savignac, Philippe

  DOI：——

  日期：——
• SmI2-mediated reactions of diethyl iodomethylphosphonate with esters and lactones: a highly stereoselective synthesis of a precursor of the C-glycosyl analogue of thymidine 5′-(β-l-rhamnosyl)diphosphate
  作者：Fulvia Orsini、Alessandro Caselli

  DOI：10.1016/s0040-4039(02)01540-x

  日期：2002.9

  In the presence of samarium iodide diethyl iodomethylphosphonate reacts with esters to afford beta-ketophosphonates. The protocol has been applied to sugar lactones to afford in fairly good yields intermediates that are useful precursors for a variety of potentially bioactive compounds, such as the C-glycosyl analogue of thymidine 5'-(beta-L-rhamnosyl)diphosphate. (C) 2002 Elsevier Science Ltd. All rights reserved.
• β-Ketophosphonate Formation via Aerobic Oxyphosphorylation of Alkynes or Alkynyl Carboxylic Acids with H-Phosphonates
  作者：Mingxin Zhou、Ming Chen、Yao Zhou、Kai Yang、Jihu Su、Jiangfeng Du、Qiuling Song

  DOI：10.1021/acs.orglett.5b00574

  日期：2015.4.3

  A synergistic Cu/Fe-catalyzed aerobic oxyphosphorylation of alkynes or alkynyl carboxylic acids with H-phosphonate is disclosed. The useful beta-ketophosphonate products were obtained in good yields under oxygen atmosphere in a novel way. This reaction exhibits a wide substrate scope, and the mechanistic experiments indicate that a radical mechanism forms both C-P and C=O bonds simultaneously. This mechanism contrasts existing aerobic difunctionalization of alkynes.
• Biocatalytic syntheses of chiral non-racemic 2-hydroxyalkanephosphonates
  作者：Remigiusz Żurawiński、Kaoru Nakamura、Józef Drabowicz、Piotr Kiełbasiński、Marian Mikołajczyk

  DOI：10.1016/s0957-4166(01)00567-5

  日期：2001.12

  A series of 2-oxoalkanephosphonates 2 were screened for reduction with Geotrichum candidum. Only diethyl 2-oxopropanephosphonate 2a underwent asymmetric reduction to give (+)-(R)-diethyl 2-hydroxypropanephosphonate 3a with 98% e.e. In turn, a series of racemic 2-hydroxyalkanephosphonates 3 were acetylated under kinetic resolution conditions in the presence of various lipases to give the corresponding 2-acetoxyalkanephosphonates 4 and recovered alcohols 3 in good yields and with e.e. up to 93%. (C) 2002 Elsevier Science Ltd. All rights reserved.