N-[(2E,4E)-5-Dimethylamino-2-(1-trifluoromethanesulfonyl-1,4-dihydro-pyridin-4-yl)-penta-2,4-dien-(E)-ylidene]-C,C,C-trifluoro-methanesulfonamide

• 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-[(2E,4E)-5-Dimethylamino-2-(1-trifluoromethanesulfonyl-1,4-dihydro-pyridin-4-yl)-penta-2,4-dien-(E)-ylidene]-C,C,C-trifluoro-methanesulfonamide
• 英文别名: (NE)-N-[(2E,4E)-5-(dimethylamino)-2-[1-(trifluoromethylsulfonyl)-4H-pyridin-4-yl]penta-2,4-dienylidene]-1,1,1-trifluoromethanesulfonamide
• 化学式: C₁₄H₁₅F₆N₃O₄S₂
• 分子量: 467.413
• InChiKey: DSSPGWGOXYWEBC-QWYOPQJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  N-(trifluoromethylsulfonyl)pyridinium trifluoromethanesulfonate 、 二甲胺 以 二氯甲烷 为溶剂， 反应 0.75h， 以34.2%的产率得到Trifluoro-methanesulfonate((2E,4E)-5-dimethylamino-penta-2,4-dienylidene)-dimethyl-ammonium;
  参考文献：
  名称：

  Nucleophilic Reactions on 1-Trifluoromethanesulfonylpyridinium Trifluoromethanesulfonate (Triflylpyridinium Triflate, TPT). Ring-Opening and "Unexpected" 1,4-Dihydropyridine Reaction Products.

  摘要：

  The reaction products of 1-trifluoromethanesulfonylpyridinium trifluoromethanesulfonate (TPT) with secondary amines have been thoroughly examined by spectroscopic and X-ray diffraction methods. The products include the normal ones expected for a ring-opening reaction (1-azahexatriene and cyanine) in addition to the "unexpected"formation of a 4-substituted 1, 4-dihydropyridine. Tandem reactions -ring-opening, nucleophilic addition- on the pyridinium ring seems to be the most probable pathway to the 1, 4-dihydropyridine compounds. Preliminary tests on the compounds revealed significant anti-microbial activity against Gram-positive bacteria, with moderate specificity towards Enterococcus faecalis.

  DOI：

  10.1248/cpb.45.957

文献信息

• Nucleophilic Reactions on 1-Trifluoromethanesulfonylpyridinium Trifluoromethanesulfonate (Triflylpyridinium Triflate, TPT). Ring-Opening and "Unexpected" 1,4-Dihydropyridine Reaction Products.
  作者：Ruben Alfredo TOSCANO、Maria del Carmen HERNANDEZ-GALINDO、Raul ROSAS、Olivia GARCIA-MELLADO、Federico del RIO PORTILLA、Carlos AMABILE-CUEVAS、Cecilio ALVAREZ-TOLEDANO

  DOI：10.1248/cpb.45.957

  日期：——

  The reaction products of 1-trifluoromethanesulfonylpyridinium trifluoromethanesulfonate (TPT) with secondary amines have been thoroughly examined by spectroscopic and X-ray diffraction methods. The products include the normal ones expected for a ring-opening reaction (1-azahexatriene and cyanine) in addition to the "unexpected"formation of a 4-substituted 1, 4-dihydropyridine. Tandem reactions -ring-opening, nucleophilic addition- on the pyridinium ring seems to be the most probable pathway to the 1, 4-dihydropyridine compounds. Preliminary tests on the compounds revealed significant anti-microbial activity against Gram-positive bacteria, with moderate specificity towards Enterococcus faecalis.