N-(1,1-dimethyl-2-propynyl)-N-methyl-benzylamine | 92039-26-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(1,1-dimethyl-2-propynyl)-N-methyl-benzylamine
• 英文别名: 1,1-dimethyl-N-benzyl-N-methyl-2-propyn-1-amine；2-(Methyl-benzyl-amino)-2-methyl-butin-(3)；Benzyl(methyl)(2-methylbut-3-yn-2-yl)amine；N-benzyl-N,2-dimethylbut-3-yn-2-amine
• CAS: 92039-26-4
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: ZQWUDPPCXFMQRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  羰基硫 、 N-(1,1-dimethyl-2-propynyl)-N-methyl-benzylamine 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 4-[benzyl(methyl)amino]-4-methylpent-2-ynethioic S-acid
  参考文献：
  名称：

  Aldehyde dehydrogenase inhibitors: α,β-Acetylenic N-substituted aminothiolesters are reversible growth inhibitors of normal epithelial but irreversible apoptogens for cancer epithelial cells from human prostate in culture

  摘要：

  The pharmacomodulation of the N atom of alpha,beta-acetylenic aminothiolesters or the replacement of the thiolester moiety by more electroplfflic groups did not permit any clear rationale to be established for improving the selective growth-inhibitory activity of this family of compounds over that of the previously synthesized alpha,beta-acetylenic aminothiolesters DIMATE and MATE [G. Quash, G. Fournet, J. Chantepie, J. Gore, C. Ardiet, D. Ardail, Y. Michal, U. Reichert, Biochem Phannacol 64 (2002) 1279-92]. Hence DIMATE and MATE were investigated more thoroughly for selectivity and growth-inhibitory activity using human prostate epithelial normal cells (HPENC) on the one hand and human prostate epithelial cancer cells (DU145) on the other. Unequivocal evidence was obtained showing that both compounds were reversible growth inhibitors of HPENC but irreversible growth inhibitors of DU145. Growth-inhibition of DU145 was due to the induction of early apoptosis as revealed by the flow cytometric analytical profile of inhibitor-treated cells, of the decrease in the redox potential and increase in superoxide anion content of their mitochondria. Of the two intracellular enzymes: aldehyde dehydrogenases 1 and 3 (ALDH1 and ALDH3) targeted by DIMATE and MATE, ALDH3 was inhibited to the same extent by both compounds whereas ALDH1 was less susceptible to inhibition by MATE. As the induction of ALDH3 by xenobiotics is hormone-dependent, MATE, the more selective of the two inhibitors, is a useful tool not only for examining the role of the ALDH3 isoform in hormone-sensitive and resistant prostate cancer cells in culture but also for investigating if it can inhibit the growth of xenografts of prostate cancer in immunodeficient mice. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.06.004
• 作为产物：
  描述：

  1,1-二甲基丙-2-炔基乙酸酯 、 N-甲基苄胺 在 C₇₀H₅₆Cl₂NO₂P₃Ru 、 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以71%的产率得到N-(1,1-dimethyl-2-propynyl)-N-methyl-benzylamine
  参考文献：
  名称：

  New five-coordinate Ru(ii) phosphoramidite complexes and their catalytic activity in propargylic amination reactions

  摘要：

  已制备出通式为[RuCl2(PPh3)2L]的前五个五配位、四方锥形的钌配合物，其中L为膦酰胺配体。这些新配合物被用作催化剂，用于丙炔酯的氨基化反应（18小时，室温或45°C，碳酸铯），以高达94%的分离产率得到丙炔胺。

  DOI：

  10.1039/c1nj20520j