6-<(n-Dodecylamino)methyl>-2-(hydroxymethyl)pyridine | 139909-49-2

• 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: 6-<(n-Dodecylamino)methyl>-2-(hydroxymethyl)pyridine
• 英文别名: {6-[(Dodecylamino)methyl]pyridin-2-YL}methanol；[6-[(dodecylamino)methyl]pyridin-2-yl]methanol
• CAS: 139909-49-2
• 化学式: C₁₉H₃₄N₂O
• 分子量: 306.492
• InChiKey: RMHCZKXDMPUXPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-<(n-Dodecylamino)methyl>-2-(hydroxymethyl)pyridine 在 氯化亚砜 作用下， 生成 (6-Chloromethyl-pyridin-2-ylmethyl)-dodecyl-amine
  参考文献：
  名称：

  Bunton, Clifford A.; Scrimin, Paolo; Tecilla, Paolo, Journal of the Chemical Society. Perkin transactions II, 1996, # 3, p. 419 - 426

  摘要：

  DOI：
• 作为产物：
  描述：

  十二烷基伯胺 、 6-Formyl-2-(carboxymethyl)pyridine 在 sodium tetrahydroborate 、 4 A molecular sieve 、 calcium chloride 作用下， 生成 6-<(n-Dodecylamino)methyl>-2-(hydroxymethyl)pyridine
  参考文献：
  名称：

  Metallomicelles as catalysts of the hydrolysis of carboxylic and phosphoric acid esters

  摘要：

  Lipophilic ligands 2-4 have been synthesized. In the presence of Cu(II) ions, they form metallomicelles that are catalytically active in the cleavage of the p-nitrophenyl esters of acetic, hexanoic, and dodecanoic acids. Catalysis was also observed in the cleavage of p-nitrophenyl diphenyl phosphate. The apparent pK(a) of the Cu(II)-coordinated hydroxyl of ligand 2a, in the micellar aggregate, is 7.7, as estimated from the rate vs pH profiles for both classes of esters: this suggests that the hydroxyl is involved as a nucleophile in the hydrolytic cleavage, which proved to be really catalytic process. The ligand bearing the free hydroxyl (2a) is more effective in the cleavage of carboxylate esters than ligands with the methylated alcoholic group (2b) or devoid of it (4); the opposite behavior is observed in the cleavage of the phosphate triester. A rationale is offered that calls for the difference in the coordination ability to the metal center of phosphate and carboxylate esters.

  DOI：

  10.1021/jo00001a033

文献信息

• Kinetics of "extraction" of copper(II) by micelle-solubilized complexing agents of varying hydrophilic lipophilic balance. 1. Stopped-flow study
  作者：Sung Geun Son、Marc Hebrant、Paolo Tecilla、Paolo Scrimin、Christian Tondre

  DOI：10.1021/j100205a082

  日期：1992.12

  Micellar particles can solubilize lipophilic extractants similarly to the organic phase in classical biphasic extraction. A series of 6-(alkylamino)methyl-2-(hydroxymethyl)pyridines (C(n)NHMePy with n = 1, 4, 8, 10, 12, 14, and 16), good complexing agents for copper(II), has been used in this work to investigate the role of hydrophobic interactions on the kinetics of complexation in micellar media. Apparent rate constants for complex formation (k(f)app) and dissociation (k(d)app) obtained from stopped-flow experiments are reported in different micellar systems (CTAB, SDS, and C12EO6), showing important variations with the value of n. These results which mainly concerned the protonated form of the extractant molecules (pH 3.5) have permitted precise determination of the role played by the electrostatic interactions. k(f)app is found to decrease more than 20 times in CTAB and about 10 times in C12EO6 for n changing from 1 to 16. The influence of copper(II) and surfactant concentrations on the observed rate constants is interpreted in terms of partition coefficients which have been independently determined from dialysis experiments. The reaction is found to be insensitive to surfactant concentration for n = 1, 4, and 8 in CTAB and only for n = 1 and 4 for C12EO6. The activation parameters are determined for n = 4 and 14 in water, in CTAB, and in C12EO6. The effect of the addition of alcohol and oil to form different o/w microemulsions is finally reported.
• SCRIMIN, PAOLO;TECILLA, PAOLO;TONELLATO, UMBERTO, J. ORG. CHEM., 56,(1991) N, C. 161-166
  作者：SCRIMIN, PAOLO、TECILLA, PAOLO、TONELLATO, UMBERTO

  DOI：——

  日期：——
• Metallomicelles as catalysts of the hydrolysis of carboxylic and phosphoric acid esters
  作者：Paolo Scrimin、Paolo Tecilla、Umberto Tonellato

  DOI：10.1021/jo00001a033

  日期：1991.1

  Lipophilic ligands 2-4 have been synthesized. In the presence of Cu(II) ions, they form metallomicelles that are catalytically active in the cleavage of the p-nitrophenyl esters of acetic, hexanoic, and dodecanoic acids. Catalysis was also observed in the cleavage of p-nitrophenyl diphenyl phosphate. The apparent pK(a) of the Cu(II)-coordinated hydroxyl of ligand 2a, in the micellar aggregate, is 7.7, as estimated from the rate vs pH profiles for both classes of esters: this suggests that the hydroxyl is involved as a nucleophile in the hydrolytic cleavage, which proved to be really catalytic process. The ligand bearing the free hydroxyl (2a) is more effective in the cleavage of carboxylate esters than ligands with the methylated alcoholic group (2b) or devoid of it (4); the opposite behavior is observed in the cleavage of the phosphate triester. A rationale is offered that calls for the difference in the coordination ability to the metal center of phosphate and carboxylate esters.
• Bunton, Clifford A.; Scrimin, Paolo; Tecilla, Paolo, Journal of the Chemical Society. Perkin transactions II, 1996, # 3, p. 419 - 426
  作者：Bunton, Clifford A.、Scrimin, Paolo、Tecilla, Paolo

  DOI：——

  日期：——