N,N'-dineopentyl-2,3-diaminopyridine | 205940-49-4

• 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-2,3-diaminopyridine
• 英文别名: 2-N,3-N-bis(2,2-dimethylpropyl)pyridine-2,3-diamine
• CAS: 205940-49-4
• 化学式: C₁₅H₂₇N₃
• 分子量: 249.399
• InChiKey: KWQFPVLZJDKOHF-UHFFFAOYSA-N

物化性质

• 沸点：
  364.6±22.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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-2,3-diaminopyridine 在 氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 31.0h， 生成 (1,3-dineopentyl-imidazolino[4,5-b]pyridin-2-ylidene)silver chloride
  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：

  2,3-二氨基吡啶 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 240.0h， 生成 N,N'-dineopentyl-2,3-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

• Anellated N-Heterocyclic Carbenes: 1,3-Dineopentylnaphtho[2,3-d]imidazol-2-ylidene: Synthesis, KOH Addition Product, Transition-Metal Complexes, and Anellation Effects
  作者：Shanmuganathan Saravanakumar、Anca I. Oprea、Markus K. Kindermann、Peter G. Jones、Joachim Heinicke

  DOI：10.1002/chem.200501183

  日期：2006.4.3

  Two novel anellated N-heterocyclic carbenes (NHC), 1,3-dineopentylnaphtho[2,3-d]imidazol-2-ylidene, and 1,3-dineopentyl-2-ylido-imidazolo[4,5-b]pyridine were obtained by reduction of the respective thiones with potassium, the former also by deprotonation of the corresponding naphthimidazolium hexafluorophosphate by using excess KH in THF. The use of equimolar amounts of KH provided an unexpected formal

  两个新颖的带电荷的N-杂环卡宾（NHC）分别是1,3-二烯戊基萘[2,3-d]咪唑-2-亚基和1,3-二烯戊基-2-ylido-咪唑并[4,5-b]吡啶通过用钾还原相应的硫酮获得前者，前者还通过在THF中使用过量的KH使相应的萘并咪唑六氟磷酸盐去质子化。等摩尔量的KH的使用提供了这种NHC与KOH的出乎意料的形式加成产物。加合物的X射线晶体结构分析提供了被两个THF分子稳定的扭曲的四聚N-杂环醇盐的证据。在C（6）D（6）中，化合物发生歧化。合成了新型萘并咪唑-2-亚烷基的过渡金属配合物[（NHC）AgCl]，[（NHC）Rh（cod）Cl]和（E）-[（NHC）（2）PdCl（2）]。X射线晶体结构以及（1）H和（13）C NMR光谱数据提供了详细的结构信息。将特征数据与无代数和不同代数的NHC或其复合物的特征数据进行比较，可提供有关扩展代数的影响的信息。
• 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。