diethyl (2,2-diphenylvinyl)phosphonate | 78462-91-6

• 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: diethyl (2,2-diphenylvinyl)phosphonate
• 英文别名: (2-diethoxyphosphoryl-1-phenylethenyl)benzene
• CAS: 78462-91-6
• 化学式: C₁₈H₂₁O₃P
• 分子量: 316.337
• InChiKey: OZWPKQDPDITEOG-UHFFFAOYSA-N

物化性质

• 沸点：
  425.0±45.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diethyl (2,2-diphenylvinyl)phosphonate 在 sodium hydroxide 、 (biscollidine)bromine(I) hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 生成 (2-溴-1-苯基乙烯基)苯
  参考文献：
  名称：

  α，β-不饱和膦酸单酯的卤代磷酸化

  摘要：

  α，β-烯键和炔属膦酸单酯与（双可力丁）碘（I）或（双可力丁）溴（I）六氟磷酸盐的反应通过无先例的去磷酸化反应导致α，β-不饱和卤化物。

  DOI：

  10.1016/j.tetlet.2005.01.089
• 作为产物：
  描述：

  diethyl phenylethynylphosphonate 在 palladium dichloride sodium hydroxide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 diethyl (2,2-diphenylvinyl)phosphonate
  参考文献：
  名称：

  Control of hydroboration of 1-alkynylphosphonates, followed by Suzuki coupling provides regio- and stereospecific synthesis of di-substituted 1-alkenylphosphonates

  摘要：

  Hydroboration of 1-alkynylphosphonates can be controlled to place boron on either C1 or C2 of the triple bond by control of reaction conditions. Initial hydroboration occurs on C1 (kinetic product), which can be isomerized to place boron on C2 (thermodynamic product) by extended heating or by use of large amounts of catalyst. Suzuki reaction of the hydroboration products with aryliodides provides a regio- and stereospecific route to disubstituted vinylphosphonates (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01696-3

文献信息

• Visible photocatalysis of novel oxime phosphonates: synthesis of β-aminophosphonates
  作者：Yong-Hong Li、Chun-Hai Wang、Su-Qian Gao、Feng-Ming Qi、Shang-Dong Yang

  DOI：10.1039/c9cc06075h

  日期：——

  A novel type of oxime phosphonate was synthesized and used in the intermolecular cascade radical addition reaction of alkenes to access β-aminophosphonates via visible-light-driven N-centered iminyl radical-mediated and redox-neutral selective C–P single-bond cleavage in an active phosphorus radical route. The procedure is characterized by its ability to achieve the construction of Csp3–P and Csp3–N

  合成了一种新型肟肟酸酯，并将其用于烯烃的分子间级联自由基加成反应中，通过可见光驱动的N中心亚胺基自由基介导的氧化还原中性选择性C–P单键裂解来获得β-氨基膦酸酯。活性磷自由基途径。该方法的特点是无需氧化剂和碱即可实现Csp 3 -P和Csp 3 -N键的构建。
• Stereoselective synthesis of vinylphosphonates and phosphine oxides via silver-catalyzed phosphorylation of styrenes
  作者：Qingwen Gui、Liang Hu、Xiang Chen、Jidan Liu、Ze Tan

  DOI：10.1039/c5cc04826e

  日期：——

  An efficient and stereoselective synthesis of vinylphosphonates and phosphine oxides was developed starting from styrenes using AgNO3 as the catalyst and K2S2O8 as the oxidant. Various vinyl-phosphonates and phosphine oxides were synthesized in good yields with excellent regioselectivity.

  从苯乙烯开始，使用AgNO 3作为催化剂，K 2 S 2 O 8作为氧化剂，开发了一种有效的立体选择性合成乙烯基膦酸酯和氧化膦的方法。以良好的产率和优异的区域选择性合成了各种乙烯基膦酸酯和氧化膦。
• Silver-promoted cascade radical cyclization of γ,δ-unsaturated oxime esters with P(O)H compounds: synthesis of phosphorylated pyrrolines
  作者：Chen Chen、Yinwei Bao、Jinghui Zhao、Bolin Zhu

  DOI：10.1039/c9cc08124k

  日期：——

  A cascade radical cyclization was realized for the first silver-promoted imino-phosphorylation of γ,δ-unsaturated oxime esters, which provided a step-economical and redox-neutral route to access a variety of phosphorylated pyrrolines in good to excellent yields. Moreover, a new bulky trivalent phosphine ligand with a pyrroline motif was obtained through a deoxidation process.

  对于第一个由银促进的γ，δ-不饱和肟酯的亚氨基磷酸化反应，实现了级联自由基环化反应，这为逐步获得经济且氧化还原中性的途径提供了一种经济高效且氧化还原中性的途径，从而能够以优异的产率获得各种磷酸化的吡咯啉。此外，通过脱氧过程获得了具有吡咯啉基序的新的庞大的三价膦配体。
• 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。
• Alkylation of .beta.-substituted styrenes by a free radical addition-elimination sequence
  作者：Glen A. Russell、Hasan Tashtoush、Preecha Ngoviwatchai

  DOI：10.1021/ja00328a057

  日期：1984.8

  On etudie les reactions des derives styryl-Q et diphenyl-1,1 vinyl-Q (Q=Bn 3 Sn, HgCl, HgB 2 , I, C 6 H 5 SO 2 , C 6 H 5 SO, C 6 H 5 S) avec des halogenures d'alkyl-Hg conduisant a divers alcenes

  在 Etudie les 反应 des 中衍生出苯乙烯基-Q 和二苯基-1,1 乙烯基-Q (Q=Bn 3 Sn, HgCl, HgB 2 , I, C 6 H 5 SO 2 , C 6 H 5 SO, C 6 H 5 S ) avec des halures d'烷基-Hg conduisant a divers alcenes