(E)-N-(2-[(8-hydroxyquinolin-2-yl)methyleneamino]benzyl)-4-methylbenzenesulfonamide | 1355955-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (E)-N-(2-[(8-hydroxyquinolin-2-yl)methyleneamino]benzyl)-4-methylbenzenesulfonamide
• CAS: 1355955-66-6
• 化学式: C₂₄H₂₁N₃O₃S
• 分子量: 431.515
• InChiKey: QJUKTZQXFSFDMR-PCLIKHOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  91.65
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 (E)-N-(2-[(8-hydroxyquinolin-2-yl)methyleneamino]benzyl)-4-methylbenzenesulfonamide 、 nickel(II) acetate tetrahydrate 以 甲醇 为溶剂， 生成 (S(C),R(N),R(C),S(N))-Ni(2-(3-tosyl-1,2,3,4-tetrahydroquinazolin-2-yl)quinolin-8-oxy)2*4methanol
  参考文献：
  名称：

  Metal-Assisted Ring-Closing/Opening Process of a Chiral Tetrahydroquinazoline

  摘要：

  The ring-chain tautomerism of a 2-aryl-1,2,3,4-tetrahydroquinazo-line has been exploited to induce reversible changes in the aminal-imine equilibrium, as desired, by coordination of a suitable metal ion. This process was studied by NMR and UV-vis spectroscopies, X-ray crystallography, and molecular modeling approach. The results obtained show that the imine H2Li undergoes a selective ring-closing reaction upon complexation with Ni2+. As a result, complexes of the type Ni(HLa)(2) are obtained, whose chirality arises from the chiral ligand H2La and the helicity of the structure. Hence, helical enantiomers form the following racemates: [Delta-C(R,R)N(S,S),Lambda-C(S,S)N(R,R)]-Ni(HLa)(2)center dot 2HOAc and [Delta,Lambda-C(S,R)N(R,S)]-Ni(HLa)(2)center dot 4MeOH. In contrast to the situation observed for Ni2+, the cyclic tautomer of the ligand, H2La, undergoes a selective ring-opening reaction upon complex formation with Pd2+, ultimately yielding Pd(HLi)(2)center dot MeOH, in which the open-chain imine ligand is bidentate through the N,O donor set of the quinoline residue. Density functional theory calculations were conducted to provide insight into the different behavior of both coordinated metals (Ni2+ and Pd2+) and to propose a mechanism for the metal-assisted opening/closing reaction of the tetrahydroquinazoline ring.

  DOI：

  10.1021/ic2017038
• 作为产物：
  描述：

  2-tosylaminomethylaniline 、 8-羟基喹啉-2-甲醛 以 氯仿 为溶剂， 反应 1.0h， 以42%的产率得到(E)-N-(2-[(8-hydroxyquinolin-2-yl)methyleneamino]benzyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Metal-Assisted Ring-Closing/Opening Process of a Chiral Tetrahydroquinazoline

  摘要：

  The ring-chain tautomerism of a 2-aryl-1,2,3,4-tetrahydroquinazo-line has been exploited to induce reversible changes in the aminal-imine equilibrium, as desired, by coordination of a suitable metal ion. This process was studied by NMR and UV-vis spectroscopies, X-ray crystallography, and molecular modeling approach. The results obtained show that the imine H2Li undergoes a selective ring-closing reaction upon complexation with Ni2+. As a result, complexes of the type Ni(HLa)(2) are obtained, whose chirality arises from the chiral ligand H2La and the helicity of the structure. Hence, helical enantiomers form the following racemates: [Delta-C(R,R)N(S,S),Lambda-C(S,S)N(R,R)]-Ni(HLa)(2)center dot 2HOAc and [Delta,Lambda-C(S,R)N(R,S)]-Ni(HLa)(2)center dot 4MeOH. In contrast to the situation observed for Ni2+, the cyclic tautomer of the ligand, H2La, undergoes a selective ring-opening reaction upon complex formation with Pd2+, ultimately yielding Pd(HLi)(2)center dot MeOH, in which the open-chain imine ligand is bidentate through the N,O donor set of the quinoline residue. Density functional theory calculations were conducted to provide insight into the different behavior of both coordinated metals (Ni2+ and Pd2+) and to propose a mechanism for the metal-assisted opening/closing reaction of the tetrahydroquinazoline ring.

  DOI：

  10.1021/ic2017038