2-[2-[Bis(dimethylamino)methylideneamino]-4,6-bis(4-oxopyridin-1-yl)-1,3,5-triaza-2lambda5-phosphacyclohexa-1,3,5-trien-2-yl]-1,1,3,3-tetramethylguanidine | 1268699-88-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-[2-[Bis(dimethylamino)methylideneamino]-4,6-bis(4-oxopyridin-1-yl)-1,3,5-triaza-2lambda5-phosphacyclohexa-1,3,5-trien-2-yl]-1,1,3,3-tetramethylguanidine
• 英文别名: 2-[2-[bis(dimethylamino)methylideneamino]-4,6-bis(4-oxopyridin-1-yl)-1,3,5-triaza-2λ5-phosphacyclohexa-1,3,5-trien-2-yl]-1,1,3,3-tetramethylguanidine
• CAS: 1268699-88-2
• 化学式: C₂₂H₃₂N₁₁O₂P
• 分子量: 513.542
• InChiKey: BAOUJNNMJKHBCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  双(乙腈)氯化钯(II) 、 2-[2-[Bis(dimethylamino)methylideneamino]-4,6-bis(4-oxopyridin-1-yl)-1,3,5-triaza-2lambda5-phosphacyclohexa-1,3,5-trien-2-yl]-1,1,3,3-tetramethylguanidine 以 乙腈 为溶剂， 以62%的产率得到[((NC(OC₅H₄N))2(NP(NC(N(CH₃)2)2)2))PdCl₂]
  参考文献：
  名称：

  Carbophosphazene-Supported Ligand Systems Containing Pyrazole/Guanidine Coordinating Groups

  摘要：

  Carbophosphazene-based coordination ligands [{NC(NMe2)}(2){NP(3,5-Me(2)Pz)(2)}] (1), [{NC(NEt)(2)}{NC(3,5-Me(2)Pz)}{NP(3,5-Me(2)Pz)(2)}] (2), [NC(3,5-Me(2)Pz)](2)[NP(3,5-Me(2)Pz)(2)] (3), [{NCCl}(2){NP(NC(NMe2)(2))(2)}] (4), and [{NC(p-OC5H4N)}(2){NP(NC(NMe2)(2))(2)}] (5) were synthesized and structurally characterized. In these compounds, the six-membered C2N3P ring is perfectly planar. The reaction of 1 with CuCl2 afforded [{NC(NMe2)}(2){NHP(O)(3,5-Me(2)Pz)}center dot{Cu(3,5-Me(2)PzH)(2)(Cl)}] [Cl] (6). The ligand binds to Cu(II) utilizing the geminal [P(O)(3,5-Me(2)Pz)] coordinating unit. Similarly, the reaction of 2. with PdCl2 afforded, after a metal-assisted P-N hydrolysis, [{NC(NEt)(2)}{NC(3,5-Me(2)Pz)}{NP(O)(3,5-Me(2)Pz)}center dot{Pd(3,5-Me(2)PzH)(Cl)}] (7). In the latter, the [P(O)(3,5-Me(2)Pz)] unit does not coordinate; in this instance, the Pd(II) is bound by a ring nitrogen atom and a carbon-tethered pyrazolyl nitrogen atom. The reaction of 3 with PdCl2 also results in P-N bond hydrolysis affording [{NC(3,5-Me(2)Pz)(2)}{NP(O)(3,5-Me(2)Pz)}{Pd(Cl)}] (8). In contrast to 7, however, in 8, the Pd(II) elicits a nongeminal eta(3) coordination from the ligand involving two carbon-tethered pyrazolyl groups and a ring nitrogen atom. Metalated products could not be isolated in the reaction of 3 with K2PtCl4. Instead, a P-O-P bridged carbodiphosphazane dimer, [{NC(3,5-Me(2)Pz)NHC(3,5-Me(2)Pz)}{NP(O)}](2) (9), was isolated as the major product. Finally, the reaction of 5 with PdCl2 resulted in [{NC(OC5H4N)}(2){NP(NC(NMe2)(2))(2)}center dot{PdCl2}] (10). In the latter, the exocyclic P-N bonds are quite robust and are involved in binding to the metal ion. Compounds 6-10 have been characterized by a variety of techniques including X-ray crystallography. In all of the compounds, the bond parameters of the inorganic heterocyclic rings are affected by metalation.

  DOI：

  10.1021/ic102415x
• 作为产物：
  描述：

  4-羟基吡啶 、 2-[2-[Bis(dimethylamino)methylideneamino]-4,6-dichloro-1,3,5-triaza-2lambda5-phosphacyclohexa-1,3,5-trien-2-yl]-1,1,3,3-tetramethylguanidine 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 49.0h， 以83%的产率得到2-[2-[Bis(dimethylamino)methylideneamino]-4,6-bis(4-oxopyridin-1-yl)-1,3,5-triaza-2lambda5-phosphacyclohexa-1,3,5-trien-2-yl]-1,1,3,3-tetramethylguanidine
  参考文献：
  名称：

  Carbophosphazene-Supported Ligand Systems Containing Pyrazole/Guanidine Coordinating Groups

  摘要：

  Carbophosphazene-based coordination ligands [{NC(NMe2)}(2){NP(3,5-Me(2)Pz)(2)}] (1), [{NC(NEt)(2)}{NC(3,5-Me(2)Pz)}{NP(3,5-Me(2)Pz)(2)}] (2), [NC(3,5-Me(2)Pz)](2)[NP(3,5-Me(2)Pz)(2)] (3), [{NCCl}(2){NP(NC(NMe2)(2))(2)}] (4), and [{NC(p-OC5H4N)}(2){NP(NC(NMe2)(2))(2)}] (5) were synthesized and structurally characterized. In these compounds, the six-membered C2N3P ring is perfectly planar. The reaction of 1 with CuCl2 afforded [{NC(NMe2)}(2){NHP(O)(3,5-Me(2)Pz)}center dot{Cu(3,5-Me(2)PzH)(2)(Cl)}] [Cl] (6). The ligand binds to Cu(II) utilizing the geminal [P(O)(3,5-Me(2)Pz)] coordinating unit. Similarly, the reaction of 2. with PdCl2 afforded, after a metal-assisted P-N hydrolysis, [{NC(NEt)(2)}{NC(3,5-Me(2)Pz)}{NP(O)(3,5-Me(2)Pz)}center dot{Pd(3,5-Me(2)PzH)(Cl)}] (7). In the latter, the [P(O)(3,5-Me(2)Pz)] unit does not coordinate; in this instance, the Pd(II) is bound by a ring nitrogen atom and a carbon-tethered pyrazolyl nitrogen atom. The reaction of 3 with PdCl2 also results in P-N bond hydrolysis affording [{NC(3,5-Me(2)Pz)(2)}{NP(O)(3,5-Me(2)Pz)}{Pd(Cl)}] (8). In contrast to 7, however, in 8, the Pd(II) elicits a nongeminal eta(3) coordination from the ligand involving two carbon-tethered pyrazolyl groups and a ring nitrogen atom. Metalated products could not be isolated in the reaction of 3 with K2PtCl4. Instead, a P-O-P bridged carbodiphosphazane dimer, [{NC(3,5-Me(2)Pz)NHC(3,5-Me(2)Pz)}{NP(O)}](2) (9), was isolated as the major product. Finally, the reaction of 5 with PdCl2 resulted in [{NC(OC5H4N)}(2){NP(NC(NMe2)(2))(2)}center dot{PdCl2}] (10). In the latter, the exocyclic P-N bonds are quite robust and are involved in binding to the metal ion. Compounds 6-10 have been characterized by a variety of techniques including X-ray crystallography. In all of the compounds, the bond parameters of the inorganic heterocyclic rings are affected by metalation.

  DOI：

  10.1021/ic102415x

文献信息

• Carbophosphazene-Supported Ligand Systems Containing Pyrazole/Guanidine Coordinating Groups
  作者：Vadapalli Chandrasekhar、Venkatasubbiah Krishnan、Ramachandran Azhakar、Tapas Senapati、Atanu Dey、R. Suriya Narayanan

  DOI：10.1021/ic102415x

  日期：2011.3.21

  Carbophosphazene-based coordination ligands [NC(NMe2)}(2)NP(3,5-Me(2)Pz)(2)}] (1), [NC(NEt)(2)}NC(3,5-Me(2)Pz)}NP(3,5-Me(2)Pz)(2)}] (2), [NC(3,5-Me(2)Pz)](2)[NP(3,5-Me(2)Pz)(2)] (3), [NCCl}(2)NP(NC(NMe2)(2))(2)}] (4), and [NC(p-OC5H4N)}(2)NP(NC(NMe2)(2))(2)}] (5) were synthesized and structurally characterized. In these compounds, the six-membered C2N3P ring is perfectly planar. The reaction of 1 with CuCl2 afforded [NC(NMe2)}(2)NHP(O)(3,5-Me(2)Pz)}center dotCu(3,5-Me(2)PzH)(2)(Cl)}] [Cl] (6). The ligand binds to Cu(II) utilizing the geminal [P(O)(3,5-Me(2)Pz)] coordinating unit. Similarly, the reaction of 2. with PdCl2 afforded, after a metal-assisted P-N hydrolysis, [NC(NEt)(2)}NC(3,5-Me(2)Pz)}NP(O)(3,5-Me(2)Pz)}center dotPd(3,5-Me(2)PzH)(Cl)}] (7). In the latter, the [P(O)(3,5-Me(2)Pz)] unit does not coordinate; in this instance, the Pd(II) is bound by a ring nitrogen atom and a carbon-tethered pyrazolyl nitrogen atom. The reaction of 3 with PdCl2 also results in P-N bond hydrolysis affording [NC(3,5-Me(2)Pz)(2)}NP(O)(3,5-Me(2)Pz)}Pd(Cl)}] (8). In contrast to 7, however, in 8, the Pd(II) elicits a nongeminal eta(3) coordination from the ligand involving two carbon-tethered pyrazolyl groups and a ring nitrogen atom. Metalated products could not be isolated in the reaction of 3 with K2PtCl4. Instead, a P-O-P bridged carbodiphosphazane dimer, [NC(3,5-Me(2)Pz)NHC(3,5-Me(2)Pz)}NP(O)}](2) (9), was isolated as the major product. Finally, the reaction of 5 with PdCl2 resulted in [NC(OC5H4N)}(2)NP(NC(NMe2)(2))(2)}center dotPdCl2}] (10). In the latter, the exocyclic P-N bonds are quite robust and are involved in binding to the metal ion. Compounds 6-10 have been characterized by a variety of techniques including X-ray crystallography. In all of the compounds, the bond parameters of the inorganic heterocyclic rings are affected by metalation.