2-diethoxyphosphoryl 1-p-tolylethenylamine | 171561-38-9

• 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: 2-diethoxyphosphoryl 1-p-tolylethenylamine
• 英文别名: (Z)-2-diethoxyphosphoryl-1-(4-methylphenyl)ethenamine
• CAS: 171561-38-9
• 化学式: C₁₃H₂₀NO₃P
• 分子量: 269.28
• InChiKey: DVKSFLJAEHAJMV-RAXLEYEMSA-N

物化性质

• 沸点：
  384.5±42.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-diethoxyphosphoryl 1-p-tolylethenylamine 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 5-(Diethoxy-phosphoryl)-2-oxo-6-p-tolyl-1,2-dihydro-pyridine-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of 5-Phosphonyl-2(1H)-pyridones from Primary b-Enaminophosphonate and Acetylenic Esters

  摘要：

  Primary beta-enaminophosphonates (2) are obtained from metallated diethyl methylphosphonate and nitriles. Reaction of enamines (2) with ethyl propiolate and dimethyl acetylenedicarboxylate yields 1:1 adducts (7) and (8), respectively. Treatment of monoadducts (7) with sodium hydride leads to 5-phosphonyl-2(1H)-pyridones (1). Functionalized enamines (8) under go thermal cyclocondensation 1 to give pyridones (9).

  DOI：

  10.3987/com-95-7147
• 作为产物：
  描述：

  甲基膦酸二乙酯 、 对甲苯腈 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 2-diethoxyphosphoryl 1-p-tolylethenylamine
  参考文献：
  名称：

  由金属化的烷基膦酸酯，腈和α，β-不饱和酮“一锅”合成多取代的吡啶

  摘要：

  描述了一种简单有效的多取代吡啶的合成方法。关键步骤是基于将锂化的β-烯氨基膦酸酯5的区域选择性加成到不饱和羰基化合物3上。当这些化合物金属化后，通过添加腈和不饱和羰基化合物，也可在“一锅”反应中从膦酸酯6获得吡啶1。

  DOI：

  10.1016/0040-4039(96)00850-7

文献信息

• A simple and efficient strategy for the preparation of 5-phosphorylated imidazol-2-ones from primary β-enaminophosphonates
  作者：Francisco Palacios、Ana MaOchoa de Retana、Julen Oyarzabal、J.M. Ezpeleta

  DOI：10.1016/s0040-4020(97)10438-0

  日期：1998.3

  An easy and efficient synthesis of imidazol-2-ones 5 substituted with a phosphonate group in the 5-position is described. The key step is a heterocyclization of functionalized enamines 3. These compounds 3 are formed by addition of primary β-enaminophosphonates 1 to diethyl azodicarboxylate 2.

  描述了在5位上被膦酸酯基团取代的咪唑-2-酮5的容易和有效的合成。关键步骤是官能化烯胺3的杂环化。这些化合物3是通过将伯β-烯氨基膦酸酯1加到偶氮二羧酸二乙酯2上而形成的。
• A new and efficient strategy for the preparation of 1,5,2-diazaphosphorines from primary β-enaminophosphonates
  作者：Francisco Palacios、Ana M. Ochoa de Retana、Julen Oyarzabal

  DOI：10.1016/s0040-4020(99)00068-x

  日期：1999.3

  A new and efficient synthesis of 1,5,2-diazaphosphorines is described. The key step is a base-induced heterocyclization of functionalized urea compounds. These compounds are formed by addition of primary beta-enaminophosphonates to isocyanates. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A “one pot” synthesis of polysubstituted pyridines from metallated alkylphosphonates, nitriles and α,β-unsaturated ketones
  作者：Francisco Palacios、Ana M. Ochoa de Retana、Julen Oyarzabal

  DOI：10.1016/0040-4039(96)00850-7

  日期：1996.6

  A simple and efficient synthesis of polysubstituted pyridines is described. The key step is based on the regioselective addition of lithiated β-enaminophosphonates 5 to unsaturated carbonyl compounds 3. Pyridines 1 can also be obtained in “one pot” reaction from phosphonates 6 when these compounds are metallated followed by addition of nitriles and unsaturated carbonyl compounds.

  描述了一种简单有效的多取代吡啶的合成方法。关键步骤是基于将锂化的β-烯氨基膦酸酯5的区域选择性加成到不饱和羰基化合物3上。当这些化合物金属化后，通过添加腈和不饱和羰基化合物，也可在“一锅”反应中从膦酸酯6获得吡啶1。
• Synthesis of 5-Phosphonyl-2(1H)-pyridones from Primary b-Enaminophosphonate and Acetylenic Esters
  作者：Francisco Palacios、Jesús García、Ana Ma Ochoa de Retana、Julen Oyarzabal

  DOI：10.3987/com-95-7147

  日期：——

  Primary beta-enaminophosphonates (2) are obtained from metallated diethyl methylphosphonate and nitriles. Reaction of enamines (2) with ethyl propiolate and dimethyl acetylenedicarboxylate yields 1:1 adducts (7) and (8), respectively. Treatment of monoadducts (7) with sodium hydride leads to 5-phosphonyl-2(1H)-pyridones (1). Functionalized enamines (8) under go thermal cyclocondensation 1 to give pyridones (9).