N-trimethylsilyl-2-amino-3-methylpyridine | 185255-26-9

• 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-trimethylsilyl-2-amino-3-methylpyridine
• 英文别名: 3-methyl-N-trimethylsilylpyridin-2-amine
• CAS: 185255-26-9
• 化学式: C₉H₁₆N₂Si
• 分子量: 180.325
• InChiKey: QWANZPNJXSEAPU-UHFFFAOYSA-N

物化性质

• 沸点：
  240.3±28.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-trimethylsilyl-2-amino-3-methylpyridine 、 9-borabicyclo[3.3.1]nonane dimer 以 neat (no solvent) 为溶剂， 以92%的产率得到N-trimethylsilyl-9-(3-methyl-2-pyridylamino)-9-borabicyclo[3.3.1]nonane
  参考文献：
  名称：

  Reaction of 9-Borabicyclo[3.3.1]nonane with N-Trimethylsilylamines – Cleavage of the N–Si or N–H Bond

  摘要：

  标题：摘要

  二聚体9-硼杂双环[3.3.1]壬烷1与N-三甲基硅基苯胺2的反应通过消除三甲基硅烷生成9-苯基-9-硼杂双环[3.3.1]壬烷5。相反，1与N-三甲基硅基-2-氨基吡啶3和4选择性地通过消除H₂生成相应的N-三甲基硅基氨基硼烷6和7。后者的反应通过形成硼烷-吡啶加合物进行。

  DOI：

  10.1515/znb-1998-0321
• 作为产物：
  描述：

  2-氨基-3-甲基吡啶 、 三甲基氯硅烷 在 三乙胺 作用下， 以 正己烷 为溶剂， 生成 N-trimethylsilyl-2-amino-3-methylpyridine
  参考文献：
  名称：

  Coupling Sign Determination and Isotope-Induced Chemical Shifts1Δ15/14N(29Si),1Δ15/14N(119Sn) and1Δ29/28Si(15N): Multinuclear Magnetic Resonance Study ofN-Trimethylsilyl-, -stannyl- and -plumbyl-Substituted 2-Aminopyridines, 2,6-Diaminopyridines and Analogous 2-Picolines

  摘要：

  2-Aminopyridines (1), 2-amino-3-methylpyridines (2) and 2,6-diaminopyridines (3), bearing N-trimethylsilyl, -stannyl or -plumbyl groups, and analogously substituted 2-picolines (4) were studied by H-1, C-13, N-15, Si-29, Sn-119 and (207)pb NMR spectroscopy Intramolecular N-Sn coordination became evident in the case of N,N-trimethylsilyl(trimethylstannyl)-2-aminopyridine (1e) and N,N-trimethylsilyl(trimethylstannyl)-N-trimethylsilyl-2,6-diaminopyridine (3f), in particular from their delta(15)N(amine) and delta(119)Sn data. Numerous coupling constants J(M,N-15) and J(M,C-13) (M=Si-29, Sn-119, Pb-207) were measured and, in the case of 2-/trimethylsilyl(trimethylstannyl)/methylpyridine (4e), absolute signs of (n)J(Sn-119,C-13) and (n+1)J(Sn-119,H-1) were determined by appropriate 2D C-13/H-1 heteronuclear shift correlations. Isotope-induced chemical shifts (1) Delta(15)/N-14(Si-29) (range -9 to -16 ppb) and (1) Delta(15/14)N(Sn-119) (range -32 to -55 ppb) were measured at natural abundance of N-15 by using Hahn-echo extended polarization transfer pulse sequences. (1) Delta(29/28)Si(N-15) values (range of -2.4 to -6.0 ppb) were measured from N-15 NMR spectra.

  DOI：

  10.1002/(sici)1097-458x(199611)34:11<921::aid-omr987>3.0.co;2-9

文献信息

• Reaction of 9-Borabicyclo[3.3.1]nonane with N-Trimethylsilylamines – Cleavage of the N–Si or N–H Bond
  作者：Bernd Wrackmeyer、Gerald Kehr、Saqib Alib

  DOI：10.1515/znb-1998-0321

  日期：1998.3.1

  The reaction of dimeric 9-borabicyclo[3.3.1]no-nane 1 with N-trimethylsilyl-aniline 2 affords 9-anilino-9-borabicyclo[3.3.1]nonane 5 by elimina­tion of trimethylsilane. In contrast, 1 reacts with the N-trimethylsilyl-2-aminopyridines 3 and 4 se­ lectively by elimination of H₂ to give the corre­sponding N-trimethylsilyl-aminoboranes 6 and 7. The latter reactions proceed via formation of bo-rane-pyridine adducts.

  标题：摘要

  二聚体9-硼杂双环[3.3.1]壬烷1与N-三甲基硅基苯胺2的反应通过消除三甲基硅烷生成9-苯基-9-硼杂双环[3.3.1]壬烷5。相反，1与N-三甲基硅基-2-氨基吡啶3和4选择性地通过消除H₂生成相应的N-三甲基硅基氨基硼烷6和7。后者的反应通过形成硼烷-吡啶加合物进行。

• Coupling Sign Determination and Isotope-Induced Chemical Shifts1Δ15/14N(29Si),1Δ15/14N(119Sn) and1Δ29/28Si(15N): Multinuclear Magnetic Resonance Study ofN-Trimethylsilyl-, -stannyl- and -plumbyl-Substituted 2-Aminopyridines, 2,6-Diaminopyridines and Analogous 2-Picolines
  作者：Bernd Wrackmeyer、Gerald Kehr、Hong Zhou、Saqib Ali

  DOI：10.1002/(sici)1097-458x(199611)34:11<921::aid-omr987>3.0.co;2-9

  日期：1996.11

  2-Aminopyridines (1), 2-amino-3-methylpyridines (2) and 2,6-diaminopyridines (3), bearing N-trimethylsilyl, -stannyl or -plumbyl groups, and analogously substituted 2-picolines (4) were studied by H-1, C-13, N-15, Si-29, Sn-119 and (207)pb NMR spectroscopy Intramolecular N-Sn coordination became evident in the case of N,N-trimethylsilyl(trimethylstannyl)-2-aminopyridine (1e) and N,N-trimethylsilyl(trimethylstannyl)-N-trimethylsilyl-2,6-diaminopyridine (3f), in particular from their delta(15)N(amine) and delta(119)Sn data. Numerous coupling constants J(M,N-15) and J(M,C-13) (M=Si-29, Sn-119, Pb-207) were measured and, in the case of 2-/trimethylsilyl(trimethylstannyl)/methylpyridine (4e), absolute signs of (n)J(Sn-119,C-13) and (n+1)J(Sn-119,H-1) were determined by appropriate 2D C-13/H-1 heteronuclear shift correlations. Isotope-induced chemical shifts (1) Delta(15)/N-14(Si-29) (range -9 to -16 ppb) and (1) Delta(15/14)N(Sn-119) (range -32 to -55 ppb) were measured at natural abundance of N-15 by using Hahn-echo extended polarization transfer pulse sequences. (1) Delta(29/28)Si(N-15) values (range of -2.4 to -6.0 ppb) were measured from N-15 NMR spectra.