diethyl (1-(m-tolyl)ethyl)phosphonate | 65797-29-7

• 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 (1-(m-tolyl)ethyl)phosphonate
• 英文别名: 1-(1-Diethoxyphosphorylethyl)-3-methylbenzene
• CAS: 65797-29-7
• 化学式: C₁₃H₂₁O₃P
• 分子量: 256.282
• InChiKey: YGSFFEQCBPBONS-UHFFFAOYSA-N

物化性质

• 沸点：
  345.0±21.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(diethoxyphosphoryl)vinyl 4-methylbenzenesulfonate 在 palladium 10% on activated carbon 、 甲酸铵 、 palladium diacetate 、 caesium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 diethyl (1-(m-tolyl)ethyl)phosphonate
  参考文献：
  名称：

  Applications of α-Phosphonovinyl Tosylates in the Synthesis of α-Arylethenylphosphonates via Suzuki–Miyaura Cross-Coupling Reactions

  摘要：

  It has been demonstrated for the first time that alpha-phosphonovinyl tosylates could efficiently couple with a range of arylboronic acids to access alpha-arylethenylphosphonates. The unprecedented procedure exhibits excellent functional group tolerance, giving the terminal vinylphosphonates in good to excellent isolated yields (60-99%) under mild reaction conditions.

  DOI：

  10.1021/ol503518h

文献信息

• Metal-free diimide reduction of alkenylphosphonates: simple and efficient protocol for the synthesis of α-substituted ethylphosphonates
  作者：Yewen Fang、Meijuan Yuan、Xiaoping Jin、Li Zhang、Ruifeng Li、Shaoshuai Yang、Mei Fang

  DOI：10.1016/j.tetlet.2016.02.057

  日期：2016.3

  A simple and straightforward method for the synthesis of α-substituted ethylphosphonates via diimide reduction strategy is described. With K3PO4 or Na2CO3 as the basic additive, a range of terminal alkenylphosphonates underwent efficient reduction by diimide generated from 2-nitrobenzenesulfonylhydrazide (NBSH) under room temperature. The high functional group tolerance of this methodology is also

  描述了一种通过二酰亚胺还原策略合成α-取代的乙基膦酸酯的简单直接的方法。以K 3 PO 4或Na 2 CO 3为基本添加剂，在室温下，一定范围内的末端链烯基膦酸酯被2-硝基苯磺酰肼（NBSH）生成的二酰亚胺有效还原。还证明了该方法具有较高的官能团耐受性。此外，我们的方法具有安全性高，反应条件温和，对设备的要求低以及化学选择性高的特点。
• Nucleophilic Alkylation of Carbenoids¹ ; III. Copper(I)-Catalysed Replacement of the Chlorine Atoms in 1,1-Dichloroalkanephosphonates by Various Substituents
  作者：Jean VILLIERAS、Alain RELIQUET、Jean NORMANT

  DOI：10.1055/s-1978-24656

  日期：——
• Applications of α-Phosphonovinyl Tosylates in the Synthesis of α-Arylethenylphosphonates via Suzuki–Miyaura Cross-Coupling Reactions
  作者：Yewen Fang、Li Zhang、Jinjian Li、Xiaoping Jin、Meijuan Yuan、Ruifeng Li、Rong Wu、Jianghua Fang

  DOI：10.1021/ol503518h

  日期：2015.2.20

  It has been demonstrated for the first time that alpha-phosphonovinyl tosylates could efficiently couple with a range of arylboronic acids to access alpha-arylethenylphosphonates. The unprecedented procedure exhibits excellent functional group tolerance, giving the terminal vinylphosphonates in good to excellent isolated yields (60-99%) under mild reaction conditions.