N1,N1,N1,N1-tetramethyl-1λ5-phosphinine-1,1-diamine | 1315511-37-5

• 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: N1,N1,N1,N1-tetramethyl-1λ5-phosphinine-1,1-diamine
• 英文别名: 1-N,1-N,1-N',1-N'-tetramethyl-1lambda5-phosphacyclohexa-1,3,5-triene-1,1-diamine；1-N,1-N,1-N',1-N'-tetramethyl-1λ5-phosphacyclohexa-1,3,5-triene-1,1-diamine
• CAS: 1315511-37-5
• 化学式: C₉H₁₇N₂P
• 分子量: 184.221
• InChiKey: YKUJMFWSQVQONV-UHFFFAOYSA-N

物化性质

• 沸点：
  75-80 °C(Press: 0.05 Torr)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N1,N1,N1,N1-tetramethyl-1λ5-phosphinine-1,1-diamine 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 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
• 作为产物：
  描述：

  allyl(bis(dimethylamino))(2-ethoxyvinyl)phosphonium bromide 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 N1,N1,N1,N1-tetramethyl-1λ5-phosphinine-1,1-diamine
  参考文献：
  名称：

  Electrocyclization of Phosphahexatrienes: An Approach to λ⁵-Phosphinines

  摘要：

  We experimentally verified an assumption that the substitution of a carbon atom with a pentavalent phosphorus atom in 1-alkoxy (dialkylamino) hexatrienes will not hamper its ability to electrocyclize. A series of 1-, 3-, and 5-phosphahexatrienes were synthesized. It was shown that parent lambda(5)-phosphinines could be synthesized by electrocyclization of the 3- and 5-phosphahexatrienes. The resultant electrocyclization is a convenient method for the synthesis of parent lambda(5)-phosphinines bearing different substituents on the phosphorus atom.

  DOI：

  10.1021/jo200847r

文献信息

• Electrocyclization of Phosphahexatrienes: An Approach to λ⁵-Phosphinines
  作者：Yurii V. Svyaschenko、Bogdan B. Barnych、Dmitriy M. Volochnyuk、Nadiya V. Shevchuk、Aleksandr N. Kostyuk

  DOI：10.1021/jo200847r

  日期：2011.8.5

  We experimentally verified an assumption that the substitution of a carbon atom with a pentavalent phosphorus atom in 1-alkoxy (dialkylamino) hexatrienes will not hamper its ability to electrocyclize. A series of 1-, 3-, and 5-phosphahexatrienes were synthesized. It was shown that parent lambda(5)-phosphinines could be synthesized by electrocyclization of the 3- and 5-phosphahexatrienes. The resultant electrocyclization is a convenient method for the synthesis of parent lambda(5)-phosphinines bearing different substituents on the phosphorus atom.
• 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.