N,N'-dineopentyl-3,4-diaminopyridine | 205940-52-9

• 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: N,N'-dineopentyl-3,4-diaminopyridine
• 英文别名: 3-N,4-N-bis(2,2-dimethylpropyl)pyridine-3,4-diamine
• CAS: 205940-52-9
• 化学式: C₁₅H₂₇N₃
• 分子量: 249.399
• InChiKey: VSSDBLOLQHXJLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N'-dineopentyl-3,4-diaminopyridine 在 ammonium hexafluorophosphate 、 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 1,3-dineopentyl-imidazolino[4,5-c]pyridin-2-ylidene
  参考文献：
  名称：

  吡啶环化对N，N'-二戊戊基-咪唑啉-2-亚基及相关过渡金属配合物的影响；与苯并，萘和喹喔啉环的比较

  摘要：

  现在已经详细报道了部分早先公开的可分离的N，N′-二戊戊基取代的非和吡啶基环化的咪唑啉-2-亚烷基及其选择的Ag，Rh和Pd配合物的合成。该化合物的结构通过多核NMR表征，部分通过晶体结构分析。将诊断结构和NMR数据与类似地用N，N'-二戊戊基取代的苯并，萘和喹喔啉环化的化合物进行比较，并通过L / Pd和L 2 / Pd催化测试了环化的影响PhB（OH）2与对溴甲苯的Suzuki-Miyaura偶联。

  DOI：

  10.1016/j.jorganchem.2019.04.001
• 作为产物：
  描述：

  3,4-二氨基吡啶 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 128.0h， 生成 N,N'-dineopentyl-3,4-diaminopyridine
  参考文献：
  名称：

  Unsymmetrical Carbene Homologues: Isolable Pyrido[ b ]‐1,3,2 λ ² ‐diazasilole, ‐germole and ‐stannole and Quantum‐Chemical Comparison with Unstable Pyrido[ c ] Isomers

  摘要：

  Reaction of the dilithium pyridine-2,3-diamide 1a-Li-2 with SiCl4 and subsequent reduction of the resulting 2a with potassium or direct ring closure with GeCl2 . dioxane or SnCl2 gave the stable carbene homologues 1,3-dineopentylpyrido[b]-1,3,2 lambda(2)-diazasilole (3a), -germole (4a) and -stannole (5a). Similarly, the dilithium pyridine-3,4-diamide 1b-Li-2 and SiCl4 furnished the pyrido[c]-1,3,2 lambda(4)-diazasilole (2b). However, attempt to obtain the silylene 3b as well as the analogous germylene and stannylene failed. Ab initio quantum chemical studies of model compounds IIIa, IIIb and benzo-1,3,2 lambda(2)-diazasilole (IIIc) reveal a comparable thermodynamic stabilization, Unexpected similarities of benzo and pyrido[b] derivatives and lower kinetic stability of carbene homologues of the pyrido[c]-type (b) correlate with high symmetry of the HOMO re charge densities in the former (IIIa has a nodal plane through the N-atom) and with unsymmetrical charge distribution in IIIb. All compounds are structurally characterized by NMR and MS, the carbene homologues also by UV and 3a by photoelectron spectroscopy.

  DOI：

  10.1002/(sici)1521-3765(19980310)4:3<541::aid-chem541>3.0.co;2-#

文献信息

• Self-Assembly of N-Heterocyclic Derivatives of Divalent Germanium, Tin, and Lead
  作者：Alexander V. Zabula、Andrey Yu. Rogachev、Robert West

  DOI：10.1002/chem.201405062

  日期：2014.12.8

  through strong intermolecular Npy→EII (E=Ge, Sn, Pb) interactions involving the nitrogen atom of a neighboring pyridine moiety. The electronic structures and stabilities of the prepared divalent derivatives of Ge, Sn, and Pb in monomeric and aggregated forms are discussed based on theoretical investigations.

  通过单晶X射线衍射分析和多核NMR光谱已成功分离出新型异常稳定的非对称N杂环亚甲基二萘嵌苯，亚锡萘和亚plum苯。它们的稳定性来自四聚体超分子聚集，其通过涉及相邻吡啶部分的氮原子的强分子间N py →E II（E = Ge，Sn，Pb）相互作用而产生。在理论研究的基础上，讨论了所制备的Ge，Sn和Pb二价衍生物单体和聚集形式的电子结构和稳定性。
• Stabilization of Unsymmetrically Annelated Imidazol-2-ylidenes with Respect to Their Higher Group 14 Homologues by n-/π-HOMO Inversion
  作者：Farman Ullah、Gabor Bajor、Tamas Veszprémi、Peter G. Jones、Joachim W. Heinicke

  DOI：10.1002/anie.200604516

  日期：2007.4.2
• Unsymmetrical Carbene Homologues: Isolable Pyrido[ <i>b</i> ]‐1,3,2 <i>λ</i> ² ‐diazasilole, ‐germole and ‐stannole and Quantum‐Chemical Comparison with Unstable Pyrido[ <i>c</i> ] Isomers
  作者：Joachim Heinicke、Anca Oprea、Markus K. Kindermann、Tamás Karpati、Laszlo Nyulászi、Tamás Veszprémi

  DOI：10.1002/(sici)1521-3765(19980310)4:3<541::aid-chem541>3.0.co;2-#

  日期：1998.3.10

  Reaction of the dilithium pyridine-2,3-diamide 1a-Li-2 with SiCl4 and subsequent reduction of the resulting 2a with potassium or direct ring closure with GeCl2 . dioxane or SnCl2 gave the stable carbene homologues 1,3-dineopentylpyrido[b]-1,3,2 lambda(2)-diazasilole (3a), -germole (4a) and -stannole (5a). Similarly, the dilithium pyridine-3,4-diamide 1b-Li-2 and SiCl4 furnished the pyrido[c]-1,3,2 lambda(4)-diazasilole (2b). However, attempt to obtain the silylene 3b as well as the analogous germylene and stannylene failed. Ab initio quantum chemical studies of model compounds IIIa, IIIb and benzo-1,3,2 lambda(2)-diazasilole (IIIc) reveal a comparable thermodynamic stabilization, Unexpected similarities of benzo and pyrido[b] derivatives and lower kinetic stability of carbene homologues of the pyrido[c]-type (b) correlate with high symmetry of the HOMO re charge densities in the former (IIIa has a nodal plane through the N-atom) and with unsymmetrical charge distribution in IIIb. All compounds are structurally characterized by NMR and MS, the carbene homologues also by UV and 3a by photoelectron spectroscopy.
• Influence of pyrido-annulation on N,N′-dineopentyl-imidazolin-2-ylidene and associated transition metal complexes; comparison with benzo-, naphtho- and quinoxalino-annulation
  作者：Farman Ullah、Saravanakumar Shanmuganathan、Claudia Schindler、Peter G. Jones、Joachim W. Heinicke

  DOI：10.1016/j.jorganchem.2019.04.001

  日期：2019.7

  The syntheses of isolable N,N′-dineopentyl-substituted non- and pyrido-annulated imidazolin-2-ylidenes and selected Ag, Rh and Pd complexes thereof, in part earlier communicated, are now reported in full detail. The compounds were structurally characterized by multinuclear NMR and in part by crystal structure analyses. Diagnostic structural and NMR data were compared with those of analogously N,N′

  现在已经详细报道了部分早先公开的可分离的N，N′-二戊戊基取代的非和吡啶基环化的咪唑啉-2-亚烷基及其选择的Ag，Rh和Pd配合物的合成。该化合物的结构通过多核NMR表征，部分通过晶体结构分析。将诊断结构和NMR数据与类似地用N，N'-二戊戊基取代的苯并，萘和喹喔啉环化的化合物进行比较，并通过L / Pd和L 2 / Pd催化测试了环化的影响PhB（OH）2与对溴甲苯的Suzuki-Miyaura偶联。