2,6-dimethyl-4-dimethylaminopyrylium iodide | 78617-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2,6-dimethyl-4-dimethylaminopyrylium iodide
• 英文别名: 2,6-dimethyl-4-(dimethylamino)pyrrylium iodide；(2,6-Dimethylpyran-4-ylidene)-dimethylazanium;iodide
• CAS: 78617-25-1
• 化学式: C₉H₁₄NO*I
• 分子量: 279.121
• InChiKey: AYWDJGWNGZTZBE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.75
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  12.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-4-dimethylaminopyrylium iodide 在 氨 、 碳酸氢铵 作用下， 反应 0.25h， 以78.4%的产率得到2,6-dimethyl-4-dimethylaminopyridine
  参考文献：
  名称：

  Peptide Coupling in the Presence of Highly Hindered Tertiary Amines

  摘要：

  Previously, 2,4,6-trimethylpyridine (collidine), due to steric shielding around the N-atom, was found to be an efficient base for effecting peptide segment coupling via azabenzotriazole-based onium-style coupling reagents. A number of even more highly hindered bases, including 2,3,5,6-tetramethylpyridine , 2, 6-di-tert-butyl-4-(dimethylamino)pyridine, triisopropylamine, and N-tert-butylmorpholine, have been compared with collidine in such reactions. Some of the newer bases showed advantages in terms of convenience in handling and maintenance of configuration during segment coupling processes, although dramatic differences based on steric effects were not observed. On the basis of results with a number of test peptides and many base-coupling reagent combinations, it was noted that most efficient results are obtained if 1 equiv of HOAt is present as an additive during the coupling process. For rapid activation of onium-style coupling reagents during stepwise solid-phase coupling reactions, the stronger base 2,6-di-tert-butyl-4-(dimethylamino)pyridine was more effective than collidine.

  DOI：

  10.1021/jo950912x
• 作为产物：
  描述：

  2,6-dimethyl-4-methoxypyrrylium iodide 生成 2,6-dimethyl-4-dimethylaminopyrylium iodide
  参考文献：
  名称：

  超酸体系中2,6-二甲基-γ-吡喃酮及其相关碱的质子核磁共振研究

  摘要：

  1 H和13 C nmr光谱表明，在HSO 3 F–SbF 5（1：1）溶液中的2,6-二甲基-4 H-吡喃-4-酮在环外氧原子处被双质子化。硫和氮类似物，分别为2,6-二甲基-4 H-噻喃-4-酮和2,6-二甲基-N-甲基-4-吡啶酮。其他相关化合物显示1 H和13 C nmr光谱以支持我们的解释。

  DOI：

  10.1039/p29810000812

文献信息

• Peptide Coupling in the Presence of Highly Hindered Tertiary Amines
  作者：Louis A. Carpino、Dumitru Ionescu、Ayman El-Faham

  DOI：10.1021/jo950912x

  日期：1996.1.1

  Previously, 2,4,6-trimethylpyridine (collidine), due to steric shielding around the N-atom, was found to be an efficient base for effecting peptide segment coupling via azabenzotriazole-based onium-style coupling reagents. A number of even more highly hindered bases, including 2,3,5,6-tetramethylpyridine , 2, 6-di-tert-butyl-4-(dimethylamino)pyridine, triisopropylamine, and N-tert-butylmorpholine, have been compared with collidine in such reactions. Some of the newer bases showed advantages in terms of convenience in handling and maintenance of configuration during segment coupling processes, although dramatic differences based on steric effects were not observed. On the basis of results with a number of test peptides and many base-coupling reagent combinations, it was noted that most efficient results are obtained if 1 equiv of HOAt is present as an additive during the coupling process. For rapid activation of onium-style coupling reagents during stepwise solid-phase coupling reactions, the stronger base 2,6-di-tert-butyl-4-(dimethylamino)pyridine was more effective than collidine.
• Nuclear magnetic resonance study of the protonation of 2,6-dimethyl-γ-pyrone and related bases in superacid systems
  作者：Victor Gold、Talat Mah

  DOI：10.1039/p29810000812

  日期：——

  is doubly protonated at the exocyclic oxygen atom. The sulphur and nitrogen analogues, 2,6-dimethyl-4H-thiopyran-4-one, and 2,6-dimethyl-N-methyl-4-pyridone, respectively, behave similarly. Other related compounds show 1H and 13C n.m.r. spectra in support of our interpretation.

  1 H和13 C nmr光谱表明，在HSO 3 F–SbF 5（1：1）溶液中的2,6-二甲基-4 H-吡喃-4-酮在环外氧原子处被双质子化。硫和氮类似物，分别为2,6-二甲基-4 H-噻喃-4-酮和2,6-二甲基-N-甲基-4-吡啶酮。其他相关化合物显示1 H和13 C nmr光谱以支持我们的解释。