2,3-dichloro-6-quinoxalinecarboxylic acid (-)-menthyl ester | 142437-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3-dichloro-6-quinoxalinecarboxylic acid (-)-menthyl ester
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2,3-dichloroquinoxaline-6-carboxylate
• CAS: 142437-62-5
• 化学式: C₁₉H₂₂Cl₂N₂O₂
• 分子量: 381.302
• InChiKey: MRRHBQKMVHDEAJ-PVXIVEMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  r-11,c-13,c-15,c-40-tetrahexyl-9,17-methano-11H,13H,15H-bisbenzo<5',6'>quinoxalino<2'',3'':2',3'><1,4>benzodioxonino<10',9':5,6:9'',10'':8,9><1,4>dioxonino<2,3-b>quinoxaline-8,18-diol 、 2,3-dichloro-6-quinoxalinecarboxylic acid (-)-menthyl ester 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以76%的产率得到(-)-3-carbo(-)menthoxy-r-9,c-11,c-13,c-15-tetrahexyl-7,17:8,16-dimetheno-9H,11H,13H,15H-quinoxalino<2''',3''':2''',3'''><1,4>benzodioxonino<10''',9''':5,6>quinoxalino<2',3':2',3'>quinoxalino<2'',3'':2'',3''><1,4>dioxonino<6'',5'':9',10'><1,4>benzodio...
  参考文献：
  名称：

  Cavitands as versatile molecular receptors

  摘要：

  X-ray crystal structure of 3.2PhF and H-1 NMR complexation studies in solution reveal the strong tendency of cavitand 3 to selectively bind aromatic guests in organic solution. The association constants (K(a)) for eight 1:1 caviplexes formed in acetone-d6 were determined. The solvation effect is largely responsible for the relatively low K(a) values observed. The orientation assumed by the guests inside the cavity is determined by dipole-dipole interactions between the host and the guest; additional CH3-pi interactions are present in the case of 3.3(CH3)2CO. The modification of the structure of 3 by introducing a suitable and furtherly modifiable substituent allowed the synsesis of optically pure chiral cavitand 5. H-1 NMR complexation studies of 5 in acetone-d6 reveal that the CH2OH group perching on top of the cavity rim affects the selectivity but not the orientation of the included aromatic guests for the 1:1 caviplexes formed.

  DOI：

  10.1021/jo00043a015
• 作为产物：
  描述：

  L-薄荷醇 、 2,3-二氯喹噁啉-6-羰酰氯 以 甲苯 为溶剂， 反应 15.0h， 以75%的产率得到2,3-dichloro-6-quinoxalinecarboxylic acid (-)-menthyl ester
  参考文献：
  名称：

  Cavitands as versatile molecular receptors

  摘要：

  X-ray crystal structure of 3.2PhF and H-1 NMR complexation studies in solution reveal the strong tendency of cavitand 3 to selectively bind aromatic guests in organic solution. The association constants (K(a)) for eight 1:1 caviplexes formed in acetone-d6 were determined. The solvation effect is largely responsible for the relatively low K(a) values observed. The orientation assumed by the guests inside the cavity is determined by dipole-dipole interactions between the host and the guest; additional CH3-pi interactions are present in the case of 3.3(CH3)2CO. The modification of the structure of 3 by introducing a suitable and furtherly modifiable substituent allowed the synsesis of optically pure chiral cavitand 5. H-1 NMR complexation studies of 5 in acetone-d6 reveal that the CH2OH group perching on top of the cavity rim affects the selectivity but not the orientation of the included aromatic guests for the 1:1 caviplexes formed.

  DOI：

  10.1021/jo00043a015

文献信息

• Cavitands as versatile molecular receptors
  作者：Paolo Soncini、Stefanio Bonsignore、Enrico Dalcanale、Franco Ugozzoli

  DOI：10.1021/jo00043a015

  日期：1992.8

  X-ray crystal structure of 3.2PhF and H-1 NMR complexation studies in solution reveal the strong tendency of cavitand 3 to selectively bind aromatic guests in organic solution. The association constants (K(a)) for eight 1:1 caviplexes formed in acetone-d6 were determined. The solvation effect is largely responsible for the relatively low K(a) values observed. The orientation assumed by the guests inside the cavity is determined by dipole-dipole interactions between the host and the guest; additional CH3-pi interactions are present in the case of 3.3(CH3)2CO. The modification of the structure of 3 by introducing a suitable and furtherly modifiable substituent allowed the synsesis of optically pure chiral cavitand 5. H-1 NMR complexation studies of 5 in acetone-d6 reveal that the CH2OH group perching on top of the cavity rim affects the selectivity but not the orientation of the included aromatic guests for the 1:1 caviplexes formed.