diethyl 2-(thiophen-3-yl)vinylphosphonate | 1165945-32-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl 2-(thiophen-3-yl)vinylphosphonate
• 英文别名: 3-(2-diethoxyphosphorylethenyl)thiophene
• CAS: 1165945-32-3
• 化学式: C₁₀H₁₅O₃PS
• 分子量: 246.267
• InChiKey: PTTJGIIROIFPGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-(thiophen-3-yl)vinylphosphonate 在 三甲基溴硅烷 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以70%的产率得到2-(thiophen-3-yl)vinylphosphonic acid
  参考文献：
  名称：

  Synthesis of 2-(Thiophen-3-yl)vinylphosphonic Acid

  摘要：

  A simple and efficient synthesis of 2-(thiophen-3-yl)vinylphosphonic acid has been developed. The title compound is obtained in 70% yield by addition of thiophene-3-carbaldehyde to lithium diethyl methylenephosphonate, followed by dehydration and hydrolysis. 1H, 13C, and 31P NMR spectra are presented for each of the intermediates.

  DOI：

  10.1080/00397910902784462
• 作为产物：
  描述：

  diethyl 2-hydroxy-2-(thiophen-3-yl)ethylphosphonate 在 盐酸 、 水 作用下， 反应 1.5h， 以91%的产率得到diethyl 2-(thiophen-3-yl)vinylphosphonate
  参考文献：
  名称：

  Synthesis of 2-(Thiophen-3-yl)vinylphosphonic Acid

  摘要：

  A simple and efficient synthesis of 2-(thiophen-3-yl)vinylphosphonic acid has been developed. The title compound is obtained in 70% yield by addition of thiophene-3-carbaldehyde to lithium diethyl methylenephosphonate, followed by dehydration and hydrolysis. 1H, 13C, and 31P NMR spectra are presented for each of the intermediates.

  DOI：

  10.1080/00397910902784462

文献信息

• Synthesis of α-Aminophosphonates by Umpolung-Enabled Cu-Catalyzed Regioselective Hydroamination
  作者：Shogo Nakamura、Soshi Nishino、Koji Hirano

  DOI：10.1021/acs.joc.2c02632

  日期：2023.1.20

  A copper-catalyzed regioselective hydroamination of α,β-unsaturated phosphonates has been developed to form corresponding α-aminophosphonates of interest in medicinal chemistry. The introduction of an umpolung, electrophilic amination strategy with the hydroxylamine derivative is the key to achieving the α-amination regioselectivity, which is otherwise difficult under the conventional nucleophilic

  已经开发了铜催化的 α,β-不饱和膦酸酯的区域选择性加氢胺化，以形成药物化学中感兴趣的相应 α-氨基膦酸酯。使用羟胺衍生物引入 umpolung 亲电胺化策略是实现 α-胺化区域选择性的关键，否则这在使用母胺的常规亲核加氢胺化条件下很难实现。还描述了使用手性双膦配体的不对称合成以及在相关甲硅烷基化反应中的应用。