4-(Decylmethylamino)pyridine | 140177-00-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(Decylmethylamino)pyridine
• 英文别名: N-Decyl-N-methylpyridin-4-amine
• CAS: 140177-00-0
• 化学式: C₁₆H₂₈N₂
• 分子量: 248.412
• InChiKey: IOLLRNZSDJGUJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,3-tetrakis(4-(dimethylamino)pyridinium-1-yl)cyclopropene tetrakis(hexafluorophosphate) 、 4-(Decylmethylamino)pyridine 以 乙腈 为溶剂， 反应 48.0h， 以34%的产率得到hexafluoro-l6-phosphane, 3-(4-(decyl(methyl)amino)pyridin-1-ium-1-yl)-1,1,2,3-tetrakis(4-(dimethylamino)pyridin-1-ium-1-yl)prop-2-en-1-ide salt
  参考文献：
  名称：

  The structure and reactivity of 1,2,3,3,-tetrakis[4-(dimethylamino)pyridinium-1-yl]cyclopropene salts

  摘要：

  The X-ray single crystal structure of 1,2,3,3-tetrakis(4-(dimethylamino)pyridinium-1-yl)cyclopropene, 1, is presented together with some reactions of 1. Both triphenylphosphine and 1-methylimidazole react with 1 to form the ring-opened products, (Z)-1-(triphenylphosphonio)-1,2,3,3-tetrakis(4-(dimethylamino)pyridinium-1-yl)allylide (6), and the isomeric (E)- and (Z)-1-(3-methylimidazolium-1-yl)-1,2,3,3-tetrakis(4-(dimethylamino)-pyridinium-1-yl)allylides (7), respectively. Cyclic voltammetry shows that 6 oxidizes to its corresponding allyl radical at 1.3 V vs SCE; the isomers of 7 oxidize at 0.48 and 0.61 V. The pK(a)'s of the conjugate acids of 6 and 7 are -1 and 3.0, respectively. Reaction of 1 with potassium nitrite gave an unexpected product, 1,1,2-tris(4-(dimethylamino)pyridinium-1-yl)ethylene. The reactivity of 1 was compared to some analogous systems, 2-phenyl-1,3,3-tris(4-(dimethylamino)pyridinium-1-yl)cyclopropene (12) and 2-phenyl-1,3,3-tris(3-methyl-imidazolium-1-yl)cyclopropene (13). The phenyl substituent significantly alters the reactivity of 12 and 13, such that both compounds do not form ring-opened products when treated with strong nucleophiles.

  DOI：

  10.1021/jo00036a027
• 作为产物：
  描述：

  4-氯吡啶盐酸盐 在 sodium hydride 作用下， 以 水 为溶剂， 反应 13.5h， 生成 4-(Decylmethylamino)pyridine
  参考文献：
  名称：

  The structure and reactivity of 1,2,3,3,-tetrakis[4-(dimethylamino)pyridinium-1-yl]cyclopropene salts

  摘要：

  The X-ray single crystal structure of 1,2,3,3-tetrakis(4-(dimethylamino)pyridinium-1-yl)cyclopropene, 1, is presented together with some reactions of 1. Both triphenylphosphine and 1-methylimidazole react with 1 to form the ring-opened products, (Z)-1-(triphenylphosphonio)-1,2,3,3-tetrakis(4-(dimethylamino)pyridinium-1-yl)allylide (6), and the isomeric (E)- and (Z)-1-(3-methylimidazolium-1-yl)-1,2,3,3-tetrakis(4-(dimethylamino)-pyridinium-1-yl)allylides (7), respectively. Cyclic voltammetry shows that 6 oxidizes to its corresponding allyl radical at 1.3 V vs SCE; the isomers of 7 oxidize at 0.48 and 0.61 V. The pK(a)'s of the conjugate acids of 6 and 7 are -1 and 3.0, respectively. Reaction of 1 with potassium nitrite gave an unexpected product, 1,1,2-tris(4-(dimethylamino)pyridinium-1-yl)ethylene. The reactivity of 1 was compared to some analogous systems, 2-phenyl-1,3,3-tris(4-(dimethylamino)pyridinium-1-yl)cyclopropene (12) and 2-phenyl-1,3,3-tris(3-methyl-imidazolium-1-yl)cyclopropene (13). The phenyl substituent significantly alters the reactivity of 12 and 13, such that both compounds do not form ring-opened products when treated with strong nucleophiles.

  DOI：

  10.1021/jo00036a027

文献信息

• The structure and reactivity of 1,2,3,3,-tetrakis[4-(dimethylamino)pyridinium-1-yl]cyclopropene salts
  作者：Amy S. Feng、Drew V. Speer、Stephen G. DiMagno、Mark S. Konings、Andrew Streitwieser

  DOI：10.1021/jo00036a027

  日期：1992.5

  The X-ray single crystal structure of 1,2,3,3-tetrakis(4-(dimethylamino)pyridinium-1-yl)cyclopropene, 1, is presented together with some reactions of 1. Both triphenylphosphine and 1-methylimidazole react with 1 to form the ring-opened products, (Z)-1-(triphenylphosphonio)-1,2,3,3-tetrakis(4-(dimethylamino)pyridinium-1-yl)allylide (6), and the isomeric (E)- and (Z)-1-(3-methylimidazolium-1-yl)-1,2,3,3-tetrakis(4-(dimethylamino)-pyridinium-1-yl)allylides (7), respectively. Cyclic voltammetry shows that 6 oxidizes to its corresponding allyl radical at 1.3 V vs SCE; the isomers of 7 oxidize at 0.48 and 0.61 V. The pK(a)'s of the conjugate acids of 6 and 7 are -1 and 3.0, respectively. Reaction of 1 with potassium nitrite gave an unexpected product, 1,1,2-tris(4-(dimethylamino)pyridinium-1-yl)ethylene. The reactivity of 1 was compared to some analogous systems, 2-phenyl-1,3,3-tris(4-(dimethylamino)pyridinium-1-yl)cyclopropene (12) and 2-phenyl-1,3,3-tris(3-methyl-imidazolium-1-yl)cyclopropene (13). The phenyl substituent significantly alters the reactivity of 12 and 13, such that both compounds do not form ring-opened products when treated with strong nucleophiles.