N-[3-(2,2-Dimethyl-propionylamino)-pyridin-2-yl]-2,2-dimethyl-propionamide | 125867-20-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[3-(2,2-Dimethyl-propionylamino)-pyridin-2-yl]-2,2-dimethyl-propionamide
• 英文别名: N-[2-(2,2-dimethylpropanoylamino)pyridin-3-yl]-2,2-dimethylpropanamide
• CAS: 125867-20-1
• 化学式: C₁₅H₂₃N₃O₂
• 分子量: 277.367
• InChiKey: UAYOBYFDLVWISJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[3-(2,2-Dimethyl-propionylamino)-pyridin-2-yl]-2,2-dimethyl-propionamide 在 lithium aluminium tetrahydride 、 正丁基锂 、 四氯化硅 、 氢化钾 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 240.5h， 生成 1,3-Dineopentylpyrido[b]-1,3,2λ²-diazasilole
  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-#
• 作为产物：
  描述：

  2,3-二氨基吡啶 、 三甲基乙酰氯 在 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 20.0h， 以50%的产率得到N-[3-(2,2-Dimethyl-propionylamino)-pyridin-2-yl]-2,2-dimethyl-propionamide
  参考文献：
  名称：

  邻取代的氨基吡啶的合成。新戊酰氨基衍生物的金属化

  摘要：

  将三种异构体新戊酰氨基吡啶以超过80％的产率进行锂化。在乙醚中，在-10°下用2.5-3当量的复合BuLi-TMEDA处理氨基吡啶衍生物。锂化物种与各种亲电试剂的反应以良好的产率提供了许多邻位取代的新戊酰氨基吡啶。仲吡啶醇被氧化成相应的氨基吡啶基酮。已合成了吡啶并嘧啶，苯并萘啶以及天然抗肿瘤生物碱玫瑰树碱的类似物，显示了该方法的多功能性。

  DOI：

  10.1002/jhet.5570260119

文献信息

• Marsais, Francis; Rovera, Jean-Claude; Turck, Alain, Journal of the Chemical Society. Perkin transactions I, 1990, # 9, p. 2611 - 2612
  作者：Marsais, Francis、Rovera, Jean-Claude、Turck, Alain、Godard, Alain、Queguiner, Guy

  DOI：——

  日期：——
• ESTEL, L.;LINARD, F.;MARSAIS, F.;GODARD, A.;QUEGUINER, G., J. HETEROCYCL. CHEM., 26,(1989) N, C. 105-112
  作者：ESTEL, L.、LINARD, F.、MARSAIS, F.、GODARD, A.、QUEGUINER, G.

  DOI：——

  日期：——
• MARSAIS, FRANCIS;ROVERA, JEAN-CLAUDE;TURCK, ALAIN;GODARD, ALAIN;QUEQUINER+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 2611-2612
  作者：MARSAIS, FRANCIS、ROVERA, JEAN-CLAUDE、TURCK, ALAIN、GODARD, ALAIN、QUEQUINER+

  DOI：——

  日期：——
• Synthesis of<i>ortho</i>-substituted aminopyridines. Metalation of pivaloylamino derivatives
  作者：L. Estel、F. Linard、F. Marsais、A. Godard、G. Quéguiner

  DOI：10.1002/jhet.5570260119

  日期：1989.1

  The three isomeric pivaloylaminopyridines were lithiated in more than 80% yields. Aminopyridine derivatives were treated by 2.5-3 equivalents of the complex BuLi-TMEDA at −10° in diethyl ether. Reaction of the lithiated species with various electrophiles afforded a number of ortho-substituted pivaloylaminopyridines in good yields. Secondary pyridine alcohols were oxidized to the corresponding aminopyridyl

  将三种异构体新戊酰氨基吡啶以超过80％的产率进行锂化。在乙醚中，在-10°下用2.5-3当量的复合BuLi-TMEDA处理氨基吡啶衍生物。锂化物种与各种亲电试剂的反应以良好的产率提供了许多邻位取代的新戊酰氨基吡啶。仲吡啶醇被氧化成相应的氨基吡啶基酮。已合成了吡啶并嘧啶，苯并萘啶以及天然抗肿瘤生物碱玫瑰树碱的类似物，显示了该方法的多功能性。
• 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.