2,2-bis(diphenylphosphino)-1-(quinolyl-8)-hydrazine | 1248801-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,2-bis(diphenylphosphino)-1-(quinolyl-8)-hydrazine
• 英文别名: 2,2-(diphenylphosphino)-1-(8-quinolyl)hydrazine；1,1-Bis(diphenylphosphanyl)-2-quinolin-8-ylhydrazine；1,1-bis(diphenylphosphanyl)-2-quinolin-8-ylhydrazine
• CAS: 1248801-79-7
• 化学式: C₃₃H₂₇N₃P₂
• 分子量: 527.545
• InChiKey: RLXQXPYNHVJDSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-bis(diphenylphosphino)-1-(quinolyl-8)-hydrazine 以 甲苯 为溶剂， 反应 1.0h， 以90%的产率得到7-[Diphenylphosphanylimino(diphenyl)-lambda5-phosphanyl]quinolin-8-amine
  参考文献：
  名称：

  Chemistry of the Phosphorus−Nitrogen Ligands. Multiple Isomeric Transformations of the Diphosphinohydrazine Bearing 8-Quinolyl Substituent: P→C, P→N, and P→P Migrations Caused by Different Factors

  摘要：

  The reaction of 8-quinolylhydrazine with 2 equiv of Ph2PCl in the presence of Et3N gives 8-[(Ph2P)(2)NNH]-Quin (1) (Quin = quinolyl) in 84% yield. The heating of 1 at 130 degrees C for 1 h in toluene results in migration of the [Ph2PNPPh2] group to a carbon atom of the quinolyl fragment to form an isomer, 7-(Ph2P-N=PPh2)-8-NH2-Quin (2). The same migration is caused by the addition of LiN(SiMe3)(2) to 1. On the contrary, lithiation of 1 with n-BuLi followed by the addition of ZnI2 (1:1) affords the aminoquinolyl-phosphazenide dinuclear complex [ZnI(8-Quin-NPPh2=N-PPh2)(KN)-N-3,N,P](2) (4), which is a result of P -> N migration. Compound 1 itself reacts with ZnI2 in THF to form 4 and protonated molecule 1 center dot HI, which rearranges to the more stable iminobiphosphine salt (Ph2P-PPh2=N-NH-Quin-8) center dot HI. Zinc iodide reacts with 2 equiv of the lithium salt of 1 without rearrangement, to form homoleptic aminoquinolyl zinc complex Zn[{(Ph2P)(2)NN-Quin-8}-k(2)N,N](2) (6). Solutions of 4 and 2 in dichloromethane show luminescence at 510 and 460 nm (quantum yields are 45% and 7%, respectively). DFT calculations were provided for possible isomers and their complexes.

  DOI：

  10.1021/ic101410u
• 作为产物：
  描述：

  8-肼基喹啉盐酸盐 、 二苯基氯化膦 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以94%的产率得到2,2-bis(diphenylphosphino)-1-(quinolyl-8)-hydrazine
  参考文献：
  名称：

  Chemistry of the Phosphorus−Nitrogen Ligands. Multiple Isomeric Transformations of the Diphosphinohydrazine Bearing 8-Quinolyl Substituent: P→C, P→N, and P→P Migrations Caused by Different Factors

  摘要：

  The reaction of 8-quinolylhydrazine with 2 equiv of Ph2PCl in the presence of Et3N gives 8-[(Ph2P)(2)NNH]-Quin (1) (Quin = quinolyl) in 84% yield. The heating of 1 at 130 degrees C for 1 h in toluene results in migration of the [Ph2PNPPh2] group to a carbon atom of the quinolyl fragment to form an isomer, 7-(Ph2P-N=PPh2)-8-NH2-Quin (2). The same migration is caused by the addition of LiN(SiMe3)(2) to 1. On the contrary, lithiation of 1 with n-BuLi followed by the addition of ZnI2 (1:1) affords the aminoquinolyl-phosphazenide dinuclear complex [ZnI(8-Quin-NPPh2=N-PPh2)(KN)-N-3,N,P](2) (4), which is a result of P -> N migration. Compound 1 itself reacts with ZnI2 in THF to form 4 and protonated molecule 1 center dot HI, which rearranges to the more stable iminobiphosphine salt (Ph2P-PPh2=N-NH-Quin-8) center dot HI. Zinc iodide reacts with 2 equiv of the lithium salt of 1 without rearrangement, to form homoleptic aminoquinolyl zinc complex Zn[{(Ph2P)(2)NN-Quin-8}-k(2)N,N](2) (6). Solutions of 4 and 2 in dichloromethane show luminescence at 510 and 460 nm (quantum yields are 45% and 7%, respectively). DFT calculations were provided for possible isomers and their complexes.

  DOI：

  10.1021/ic101410u

文献信息

• New rearrangements of phosphorus-nitrogen ligands
  作者：Yu. S. Panova、A. N. Kornev、V. V. Sushchev、A. V. Cherkasov、G. A. Abakumov

  DOI：10.1134/s0012500812080058

  日期：2012.8
• Chemistry of the Phosphorus−Nitrogen Ligands. Multiple Isomeric Transformations of the Diphosphinohydrazine Bearing 8-Quinolyl Substituent: P→C, P→N, and P→P Migrations Caused by Different Factors
  作者：Alexander N. Kornev、Natalia V. Belina、Vyacheslav V. Sushev、Julia S. Panova、Olga V. Lukoyanova、Sergey Y. Ketkov、Georgy K. Fukin、Mikhail A. Lopatin、Gleb A. Abakumov

  DOI：10.1021/ic101410u

  日期：2010.10.18

  The reaction of 8-quinolylhydrazine with 2 equiv of Ph2PCl in the presence of Et3N gives 8-[(Ph2P)(2)NNH]-Quin (1) (Quin = quinolyl) in 84% yield. The heating of 1 at 130 degrees C for 1 h in toluene results in migration of the [Ph2PNPPh2] group to a carbon atom of the quinolyl fragment to form an isomer, 7-(Ph2P-N=PPh2)-8-NH2-Quin (2). The same migration is caused by the addition of LiN(SiMe3)(2) to 1. On the contrary, lithiation of 1 with n-BuLi followed by the addition of ZnI2 (1:1) affords the aminoquinolyl-phosphazenide dinuclear complex [ZnI(8-Quin-NPPh2=N-PPh2)(KN)-N-3,N,P](2) (4), which is a result of P -> N migration. Compound 1 itself reacts with ZnI2 in THF to form 4 and protonated molecule 1 center dot HI, which rearranges to the more stable iminobiphosphine salt (Ph2P-PPh2=N-NH-Quin-8) center dot HI. Zinc iodide reacts with 2 equiv of the lithium salt of 1 without rearrangement, to form homoleptic aminoquinolyl zinc complex Zn[(Ph2P)(2)NN-Quin-8}-k(2)N,N](2) (6). Solutions of 4 and 2 in dichloromethane show luminescence at 510 and 460 nm (quantum yields are 45% and 7%, respectively). DFT calculations were provided for possible isomers and their complexes.