naphthylmethylphosphonic acid methyl ester | 764621-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthylmethylphosphonic acid methyl ester
• 英文别名: Methoxy(naphthalen-1-ylmethyl)phosphinic acid
• CAS: 764621-31-0
• 化学式: C₁₂H₁₃O₃P
• 分子量: 236.207
• InChiKey: NPKXBNBTVRAVCX-UHFFFAOYSA-N

物化性质

• 沸点：
  413.7±38.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  naphthylmethylphosphonic acid methyl ester 在 dichlorobis(triethylphosphine)palladium(II) 、 potassium hydrogen bifluoride 、 N-乙酰-L-缬氨酸 、 silver(l) oxide 作用下， 以 乙醚 、 叔丁醇 为溶剂， 反应 24.5h， 生成 dimethyl (2-phenylnaphthalen-1-yl)methylphosphonate
  参考文献：
  名称：

  Palladium(II)-Catalyzed Ortho-Arylation of Benzylic Phosphonic Monoesters Using Potassium Aryltrifluoroborates

  摘要：

  The new monophosphonic acid directing group was successfully utilized in the Pd (II)-catalyzed orthoarylation of benzylic phosphonic monoesters using potassium aryltrifluoroborates. A wide range of benzylic phosphonic monoesters underwent clean ortho-arylation in high yields, and excellent functional group tolerance was also observed.

  DOI：

  10.1021/jo401716p
• 作为产物：
  描述：

  1-萘甲醇 在 氯化亚砜 、 N,N-二甲基甲酰胺 、 zinc(II) iodide 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 naphthylmethylphosphonic acid methyl ester
  参考文献：
  名称：

  Palladium(II)-Catalyzed Ortho-Arylation of Benzylic Phosphonic Monoesters Using Potassium Aryltrifluoroborates

  摘要：

  The new monophosphonic acid directing group was successfully utilized in the Pd (II)-catalyzed orthoarylation of benzylic phosphonic monoesters using potassium aryltrifluoroborates. A wide range of benzylic phosphonic monoesters underwent clean ortho-arylation in high yields, and excellent functional group tolerance was also observed.

  DOI：

  10.1021/jo401716p

文献信息

• Palladium(II)-Catalyzed <i>ortho</i>-Olefination of Benzylic Phosphonic Monoesters
  作者：Xiangjian Meng、Sunggak Kim

  DOI：10.1021/ol400565r

  日期：2013.4.19

  The new monophosphonic acid directing group is successfully utilized in the Pd(II)-catalyzed ortho-olefination of benzylic phosphonic monoesters and offers further development of other phosphoryl-related directing groups in the transition-metal-catalyzed C-H activations.
• <i>ortho</i>-Acetoxylation of Phosphonic and Phosphoric Monoacids via Pd(II) Catalysis
  作者：Li Yan Chan、Xiangjian Meng、Sunggak Kim

  DOI：10.1021/jo4011188

  日期：2013.9.6

  A simple and efficient method is developed for Pd-catalyzed ortho-acetoxylation using organophosphates, namely, benzylic phosphonic and aryl phosphoric monoacids, as the directing group.
• Palladium(II)-Catalyzed Ortho-Arylation of Benzylic Phosphonic Monoesters Using Potassium Aryltrifluoroborates
  作者：Xiangjian Meng、Sunggak Kim

  DOI：10.1021/jo401716p

  日期：2013.11.15

  The new monophosphonic acid directing group was successfully utilized in the Pd (II)-catalyzed orthoarylation of benzylic phosphonic monoesters using potassium aryltrifluoroborates. A wide range of benzylic phosphonic monoesters underwent clean ortho-arylation in high yields, and excellent functional group tolerance was also observed.