C4H4N-P(S)(OEt)2 | 54006-01-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: C4H4N-P(S)(OEt)2
• 英文别名: Diaethoxy-(1-pyrryl)-phosphinsulfid；Diethoxy-pyrrol-1-yl-sulfanylidene-lambda5-phosphane；diethoxy-pyrrol-1-yl-sulfanylidene-λ5-phosphane
• CAS: 54006-01-8
• 化学式: C₈H₁₄NO₂PS
• 分子量: 219.244
• InChiKey: AUHQVUYTWSSLDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  C4H4N-P(S)(OEt)2 在 正丁基锂 作用下， 以95%的产率得到O,O'-diethyl pyrrol-2-ylthiophosphonate
  参考文献：
  名称：

  通过 A [1,2] 或 [1,3] Phospho-Fries 重排合成芳基硫代膦酸酯

  摘要：

  摘要 O,O-二乙基芳基硫代膦酸酯的合成是在碱诱导的 [1,2] 或 [1,3] 磷酸-弗里斯重排之后实现的，该重排利用 O,O-二乙基 O-芳基硫代磷酸酯作为底物。还讨论了 O,O-二乙基芳基硫代膦酸酯的配位性质。

  DOI：

  10.1080/10426507.2010.520291
• 作为产物：
  描述：

  吡咯 、 O,O-二乙基硫代磷酰氯 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以91%的产率得到C4H4N-P(S)(OEt)2
  参考文献：
  名称：

  Application of a base-induced [1,2]-rearrangement to synthesize thiophosphonate bidentate S(sp2)–N monoanionic ligand: Characterization of its silver and palladium complexes

  摘要：

  The O, O-diethyl thiophosphonate functional group has been introduced on position 2 of a pyrrole heterocycle following a two steps sequence that makes use of a [1,2] base-induced rearrangement applied for the first time to a O, O- diethyl thiophosphoramide intermediate. This rearrangement has been studied by low temperature NMR and the intermediates have been fully characterized. The coordination of this monoanionic bidentate (N,Ssp(2)) ligand to silver or palladium is studied The bidentate ligand 2 (O,O-diethyl pyrrol-2-ylthiophosphonate), associated with a palladium precursor, produces in the presence of triethylamine the complex trans-[Pd(eta(2)-2')(2)] 3 (2' is deprotonated ligand 2). Ligand 2 also reacts with silver oxide in dichloromethane to give an unstable complex 2'-Ag that can be stabilized by addition of triphenylphosphine to produce the coordination complex 4 [Ag((eta(2)-2')(PPh3)(2)]. (C) 2009 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.08.035

文献信息

• Application of a base-induced [1,2]-rearrangement to synthesize thiophosphonate bidentate S(sp2)–N monoanionic ligand: Characterization of its silver and palladium complexes
  作者：Sabrina Marie、Martin Lutz、Anthony L. Spek、Robertus J.M. Klein Gebbink、Gerard van Koten、Nelly Kervarec、François Michaud、Jean-Yves Salaün、Paul-Alain Jaffrès

  DOI：10.1016/j.jorganchem.2009.08.035

  日期：2009.12

  The O, O-diethyl thiophosphonate functional group has been introduced on position 2 of a pyrrole heterocycle following a two steps sequence that makes use of a [1,2] base-induced rearrangement applied for the first time to a O, O- diethyl thiophosphoramide intermediate. This rearrangement has been studied by low temperature NMR and the intermediates have been fully characterized. The coordination of this monoanionic bidentate (N,Ssp(2)) ligand to silver or palladium is studied The bidentate ligand 2 (O,O-diethyl pyrrol-2-ylthiophosphonate), associated with a palladium precursor, produces in the presence of triethylamine the complex trans-[Pd(eta(2)-2')(2)] 3 (2' is deprotonated ligand 2). Ligand 2 also reacts with silver oxide in dichloromethane to give an unstable complex 2'-Ag that can be stabilized by addition of triphenylphosphine to produce the coordination complex 4 [Ag((eta(2)-2')(PPh3)(2)]. (C) 2009 Elsevier B. V. All rights reserved.
• Synthesis of Aryl-Thiophosphonates via A [1,2] or [1,3] Phospho-Fries Rearrangement
  作者：Céline Denis、Aurore Fraix、Mathieu Berchel、Jean-Yves Salaün、Paul-Alain Jaffrès

  DOI：10.1080/10426507.2010.520291

  日期：2011.3.31

  Abstract The synthesis of O,O-diethyl arylthiophosphonates is achieved following a base-induced [1,2] or [1,3] phospho-Fries rearrangement that makes use of O,O-diethyl O-aryl thiophosphates as substrates. The coordination properties of O,O-diethyl arylthiophosphonates are also discussed.

  摘要 O,O-二乙基芳基硫代膦酸酯的合成是在碱诱导的 [1,2] 或 [1,3] 磷酸-弗里斯重排之后实现的，该重排利用 O,O-二乙基 O-芳基硫代磷酸酯作为底物。还讨论了 O,O-二乙基芳基硫代膦酸酯的配位性质。