diethyl (E)-2-(3-methoxyphenyl)ethenylphosphonate | 202476-39-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl (E)-2-(3-methoxyphenyl)ethenylphosphonate
• 英文别名: (E)-diethyl (3-methoxylstyryl)phosphonate；diethyl (Ε)-2-(3-methoxyphenyl)vinylphosphonate；(E)-diethyl 3-methoxystyrylphosphonate；1-[(E)-2-diethoxyphosphorylethenyl]-3-methoxybenzene
• CAS: 202476-39-9
• 化学式: C₁₃H₁₉O₄P
• 分子量: 270.265
• InChiKey: FNPROIJPVFEBAJ-MDZDMXLPSA-N

物化性质

• 沸点：
  380.0±34.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (E)-2-(3-methoxyphenyl)ethenylphosphonate 在 potassium osmate(VI) AD-mix-α 、 甲基磺酰胺 作用下， 以 水 、 叔丁醇 为溶剂， 反应 50.0h， 以67%的产率得到diethyl (1S,2S)-1,2-dihydroxy-2-(3-methoxyphenyl)ethylphosphonate
  参考文献：
  名称：

  Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents

  摘要：

  Asymmetric dihydroxylation (AD) of 1(E)-alkenylphosphonates with an AD-mix -alpha or -beta reagent was examined to give a series of optically active threo-alpha,beta-dihydroxyphosphonates. Good enantioselectivity (>88% eel was observed in the AD reaction of 1(E)-alkenylphosphonates with conjugated aromatic substituents. The steric effects of the ester functionality in the course of the dihydroxylation were also evaluated. Enantioselectivity and yield were significantly improved when the AD reaction was carried out with dimethyl phosphonate instead of diethyl phosphonate. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10341-6
• 作为产物：
  描述：

  亚甲基二磷酸四乙酯 、 3-甲氧基苯甲醛 在 正丁基锂 作用下， 以 正己烷 、 四氢呋喃 为溶剂， 反应 5.2h， 以74%的产率得到diethyl (E)-2-(3-methoxyphenyl)ethenylphosphonate
  参考文献：
  名称：

  Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents

  摘要：

  Asymmetric dihydroxylation (AD) of 1(E)-alkenylphosphonates with an AD-mix -alpha or -beta reagent was examined to give a series of optically active threo-alpha,beta-dihydroxyphosphonates. Good enantioselectivity (>88% eel was observed in the AD reaction of 1(E)-alkenylphosphonates with conjugated aromatic substituents. The steric effects of the ester functionality in the course of the dihydroxylation were also evaluated. Enantioselectivity and yield were significantly improved when the AD reaction was carried out with dimethyl phosphonate instead of diethyl phosphonate. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10341-6

文献信息

• TEMPO and Silver-Mediated Intermolecular Phosphonylation of Alkenes: Stereoselective Synthesis of (<i>E</i> )-Alkenylphosphonates
  作者：Lei Wang、Zhen Yang、Huijuan Zhu、Haitao Liu、Shuaipeng Lv、Yue Xu

  DOI：10.1002/ejoc.201801678

  日期：2019.3.21

  An efficient and novel method was developed towards the synthesis of alkenylphosphonates from simple olefins and phosphonate diesters. This method was enabled by the use of cheap and commercially available silver salts and TEMPO. This method exhibits of good functional group tolerance, specific (E)‐selectivity for all olefins and vinyl‐selectivity for aliphatic olefins. A radical mechanism was proposed

  为从简单的烯烃和膦酸酯二酯合成链烯基膦酸酯开发了一种有效且新颖的方法。通过使用便宜的和可商购的银盐和TEMPO，可以实现此方法。该方法具有良好的官能团耐受性，对所有烯烃的比选择性（E）-选择性和对脂肪族烯烃的乙烯基-选择性。提出了一种根本机理，并且TEMPO参与了产物形成步骤。
• 一种(E)-2-芳基乙烯基膦酸酯衍生物的制备方 法
  申请人：江苏强盛功能化学股份有限公司

  公开号：CN104277072B

  公开（公告）日：2016-04-13

  本发明公开了一种(E)-2-芳基乙烯基膦酸酯衍生物的制备方法，具体为将1-硝基-2-芳基乙烯衍生物、磷试剂、促进剂乙酸锰和催化剂乙酸铜溶于溶剂中，于20~100℃下反应，获得（E）-2-芳基乙烯基膦酸酯衍生物；本发明使用1-硝基-2-芳基乙烯衍生物为起始物，原料易得、种类很多；利用本发明的方法得到的产物类型多样，既可以直接使用、又可以用于其他进一步的反应；本发明方法避免使用贵金属试剂和其他添加剂；同时，合成路线简短、反应条件温和、反应操作和后处理过程简单、产率高，适合于规模化生产。
• Manganese(<scp>iii</scp>)-mediated alkenyl C_sp2–P bond formation from the reaction of β-nitrostyrenes with dialkyl phosphites
  作者：Jian-Fei Xue、Shao-Fang Zhou、Ye-Ye Liu、Xiangqiang Pan、Jian-Ping Zou、Olayinka Taiwo Asekun

  DOI：10.1039/c5ob00404g

  日期：——

  Mn(OAc)₃-mediated tandem phosphonyl radical addition to β-nitrostyrenes followed by denitration to form (E)-2-alkenyl phosphonates is described.

  通过Mn(OAc)₃介导的串联磷酰基自由基加成到β-硝基苯乙烯，然后脱硝形成(E)-2-烯基磷酸酯。
• Base-Free Mizoroki−Heck Reaction Catalyzed by Rhodium Complexes
  作者：Rémi Martinez、Florina Voica、Jean-Pierre Genet、Sylvain Darses

  DOI：10.1021/ol071098q

  日期：2007.8.1

  A base-free rhodium-catalyzed Mizoroki-Heck (M-H) reaction using potassium aryltrifluoroborates as the arylating agent of alkenes and acetone as a green '' oxidant '' is described. Thanks to the ready availability of organoboranes, this reaction should constitute an interesting alternative to conventional M-H reactions using aryl halides.
• Chemoselective Hydrogenation of α,β-Unsaturated Sulfones and Phosphonates via Palladium-Assisted Hydrogen Transfer by Ammonium Formate
  作者：Brindaban C. Ranu、Sankar K. Guchhait、Keya Ghosh

  DOI：10.1021/jo980128n

  日期：1998.7.1