(1S,2S)-N-<<9-<(N-Methyldodecylamino)methyl>-1,10-phenanthrolin-2-yl>methyl>ephedrine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: (1S,2S)-N-<<9-<(N-Methyldodecylamino)methyl>-1,10-phenanthrolin-2-yl>methyl>ephedrine
• 英文别名: (1S,2S)-N-({9-[(N-Methyldodecylamino)methyl]-1,10-phenanthrolin-2-yl}methyl)ephedrine；(1S,2S)-2-[[9-[[dodecyl(methyl)amino]methyl]-1,10-phenanthrolin-2-yl]methyl-methylamino]-1-phenylpropan-1-ol
• 化学式: C₃₇H₅₂N₄O
• 分子量: 568.846
• InChiKey: MYHQZNFFSPMAGJ-LUPQGNFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-十二烷基甲胺 、 (1S,2S)-2-甲氨基-1-苯基丙-1-醇 、 2,9-bis-(bromomethyl)-1,10-phenantroline 在 三乙胺 作用下， 生成 (1S,2S)-N-<<9-<(N-Methyldodecylamino)methyl>-1,10-phenanthrolin-2-yl>methyl>ephedrine
  参考文献：
  名称：

  Synthesis of chiral 1,10-phenanthroline ligands and the activity of metal-ion complexes in the enantioselective hydrolysis of N-protected amino acid esters

  摘要：

  The synthesis of seven new, chiral 1,10-phenanthrolines (1-7) containing a 2-pyrrolidinemethanol or ephedrine substitutent at the alpha-position is reported. The catalytic activity of Zn2+, Co2+, Cu2+, Ni2+, and Cd2+ complexes of these ligands in the hydrolysis of p-nitrophenyl esters of picolinic acid (PNPP) and chiral N-protected amiDo acids was examined in water and micellar solution. The Zn2+ Comp]ex of the chiral, asymmetrically disubstituted (S)-1-[[9-[(N-methyldodecylamino)methyl]-1,10-phenanthrolin-2-yl]mehyl]-2-pyrrolidinemethanol (1) exhibits the highest activity toward PNPP. The highest enantioselectivity m the stereoselective hydrolysis of p-nitrophenyl N-dodecanoyl-D(L)-phenylalaninate (D(L)-C12-Phe-PNP) is observed for 1-Co2+ solubilized in Brij 35 micelles (k(D)a,obs/k(L)a,obs = 15.3). In a mixed micellar system of 1-Zn2+ with Brij 35 as the cosurfactant, hydrolysis of D-C12-Phe-PNP predominates over that of the L-enantiomer (k(D)a,obs/k(a,obs) = 2.4), whereas with CTABr as the cosurfactant an inversion of enantioselectivity is observed (k(D)a,obs/k(L)a,obs = 0.54).

  DOI：

  10.1021/jo00052a047

文献信息

• Synthesis of chiral 1,10-phenanthroline ligands and the activity of metal-ion complexes in the enantioselective hydrolysis of N-protected amino acid esters
  作者：John G. J. Weijnen、Arie Koudijs、Johan F. J. Engbersen

  DOI：10.1021/jo00052a047

  日期：1992.12

  The synthesis of seven new, chiral 1,10-phenanthrolines (1-7) containing a 2-pyrrolidinemethanol or ephedrine substitutent at the alpha-position is reported. The catalytic activity of Zn2+, Co2+, Cu2+, Ni2+, and Cd2+ complexes of these ligands in the hydrolysis of p-nitrophenyl esters of picolinic acid (PNPP) and chiral N-protected amiDo acids was examined in water and micellar solution. The Zn2+ Comp]ex of the chiral, asymmetrically disubstituted (S)-1-[[9-[(N-methyldodecylamino)methyl]-1,10-phenanthrolin-2-yl]mehyl]-2-pyrrolidinemethanol (1) exhibits the highest activity toward PNPP. The highest enantioselectivity m the stereoselective hydrolysis of p-nitrophenyl N-dodecanoyl-D(L)-phenylalaninate (D(L)-C12-Phe-PNP) is observed for 1-Co2+ solubilized in Brij 35 micelles (k(D)a,obs/k(L)a,obs = 15.3). In a mixed micellar system of 1-Zn2+ with Brij 35 as the cosurfactant, hydrolysis of D-C12-Phe-PNP predominates over that of the L-enantiomer (k(D)a,obs/k(a,obs) = 2.4), whereas with CTABr as the cosurfactant an inversion of enantioselectivity is observed (k(D)a,obs/k(L)a,obs = 0.54).