1,1-dimethoxyphosphinine | 32323-37-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 磷环化合物
• 英文名称: 1,1-dimethoxyphosphinine
• 英文别名: 1,1-Dimethoxy-λ⁵-phosphorin；1,1-Dimethoxy-1lambda5-phosphacyclohexa-1,3,5-triene；1,1-dimethoxy-1λ5-phosphacyclohexa-1,3,5-triene
• CAS: 32323-37-8
• 化学式: C₇H₁₁O₂P
• 分子量: 158.137
• InChiKey: GEDRWJSHXFWDNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-dimethoxyphosphinine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 68.0h， 以15%的产率得到磷杂苯
  参考文献：
  名称：

  Reduction of λ ⁵ ‐Phosphinines

  摘要：

  AbstractA convenient method to easily prepare parent λ3‐phosphinine from easily accessible λ5‐precursors was developed. A series of λ5‐phosphinines bearing heteroatom substituents OMe, SMe, and/or NMe2 at the phosphorus atom were prepared by electrocyclization of phosphahexatrienes generated in situ. Reaction conditions for the synthesis of λ5‐phosphinines were optimized. The molecular structure of 1,1‐dimethoxy‐λ5‐phosphinine was determined by an X‐ray diffraction analysis. A series of reducing agents were tested in order to prepare λ3‐phosphinine. 1,1‐Dimethoxy‐λ5‐phosphinine was reduced by LiAlH4. The method of choice appeared to be the reduction of bis(dimethylamino)‐λ5‐phosphinine with diisobutylaluminium hydride (DIBAL‐H) in 30 % overall yield starting from vinyl ethyl ether.

  DOI：

  10.1002/ejic.201500856
• 作为产物：
  描述：

  (E)-p-allyl-p-(2-ethoxyvinyl)-N,N-dimethylphosphinoselenoic amide 在 正丁基锂 、 potassium tert-butylate 、 过氧化脲素 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 1,1-dimethoxyphosphinine
  参考文献：
  名称：

  Reduction of λ ⁵ ‐Phosphinines

  摘要：

  AbstractA convenient method to easily prepare parent λ3‐phosphinine from easily accessible λ5‐precursors was developed. A series of λ5‐phosphinines bearing heteroatom substituents OMe, SMe, and/or NMe2 at the phosphorus atom were prepared by electrocyclization of phosphahexatrienes generated in situ. Reaction conditions for the synthesis of λ5‐phosphinines were optimized. The molecular structure of 1,1‐dimethoxy‐λ5‐phosphinine was determined by an X‐ray diffraction analysis. A series of reducing agents were tested in order to prepare λ3‐phosphinine. 1,1‐Dimethoxy‐λ5‐phosphinine was reduced by LiAlH4. The method of choice appeared to be the reduction of bis(dimethylamino)‐λ5‐phosphinine with diisobutylaluminium hydride (DIBAL‐H) in 30 % overall yield starting from vinyl ethyl ether.

  DOI：

  10.1002/ejic.201500856

文献信息

• Reduction of λ ⁵ ‐Phosphinines
  作者：Aleksandr Savateev、Yurii Vlasenko、Nataliya Shtil、Aleksandr Kostyuk

  DOI：10.1002/ejic.201500856

  日期：2016.2

  AbstractA convenient method to easily prepare parent λ3‐phosphinine from easily accessible λ5‐precursors was developed. A series of λ5‐phosphinines bearing heteroatom substituents OMe, SMe, and/or NMe2 at the phosphorus atom were prepared by electrocyclization of phosphahexatrienes generated in situ. Reaction conditions for the synthesis of λ5‐phosphinines were optimized. The molecular structure of 1,1‐dimethoxy‐λ5‐phosphinine was determined by an X‐ray diffraction analysis. A series of reducing agents were tested in order to prepare λ3‐phosphinine. 1,1‐Dimethoxy‐λ5‐phosphinine was reduced by LiAlH4. The method of choice appeared to be the reduction of bis(dimethylamino)‐λ5‐phosphinine with diisobutylaluminium hydride (DIBAL‐H) in 30 % overall yield starting from vinyl ethyl ether.