[6]cavitand

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: [6]cavitand
• 英文别名: 6,12,18,24,30,59-Hexamethyl-2,4,8,10,14,16,20,22,26,28,32,34-dodecaoxatridecacyclo[33.23.1.136,58.05,56.07,54.011,52.013,50.017,48.019,46.023,44.025,42.029,40.031,38]hexaconta-1(59),5,7(54),11,13(50),17,19(46),23(44),24,29(40),30,35,38,42,47,51,55,58(60)-octadecaene；6,12,18,24,30,59-hexamethyl-2,4,8,10,14,16,20,22,26,28,32,34-dodecaoxatridecacyclo[33.23.1.136,58.05,56.07,54.011,52.013,50.017,48.019,46.023,44.025,42.029,40.031,38]hexaconta-1(59),5,7(54),11,13(50),17,19(46),23(44),24,29(40),30,35,38,42,47,51,55,58(60)-octadecaene
• 化学式: C₅₄H₄₈O₁₂
• 分子量: 888.968
• InChiKey: HDJUAOCRECSJIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  66
• 可旋转键数：
  0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  二乙氧基甲烷 、 溴氯甲烷 、 2,6-二羟基甲苯 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 1.0h， 以13.9%的产率得到[6]cavitand
  参考文献：
  名称：

  Expanding Cavitand Chemistry: The Preparation and Characterization of [n]Cavitands withn≥4

  摘要：

  The preparation of cavitands composed of 4, 5, 6, and 7 aromatic subunits ([n]cavitands, n = 4-7) is described. The simple, two-step synthetic procedure utilized readily available starting materials (2-methylresorcinol and diethoxymethane). The two cavitand products having 4 and 5 aromatic subunits exhibited highly symmetric cone conformations, while the larger cavitands (n = 6 and 7) adopt conformations of lower symmetry, H-1 NMR spectroscopic studies of [6]cavitand and [7]cavitand revealed that these hosts undergo exchange between equivalent conformations at room temperature. The departure of these two cavitands from cone conformations is related to steric crowding on their Ar-O-CH2-O-Ar bridges and is predicted by simple molecular mechanics calculations (MM2 force field). X-ray diffraction studies on single crystals of the [4]cavitand, [5]cavitand, and [6]cavitand hosts afforded additional experimental support for these conclusions.

  DOI：

  10.1002/1521-3765(20010417)7:8<1637::aid-chem16370>3.0.co;2-x

文献信息

• Expanding Cavitand Chemistry: The Preparation and Characterization of [n]Cavitands withn≥4
  作者：Christoph Naumann、Esteban Román、Carlos Peinador、Tong Ren、Brian O. Patrick、Angel E. Kaifer、John C. Sherman

  DOI：10.1002/1521-3765(20010417)7:8<1637::aid-chem16370>3.0.co;2-x

  日期：2001.4.17

  The preparation of cavitands composed of 4, 5, 6, and 7 aromatic subunits ([n]cavitands, n = 4-7) is described. The simple, two-step synthetic procedure utilized readily available starting materials (2-methylresorcinol and diethoxymethane). The two cavitand products having 4 and 5 aromatic subunits exhibited highly symmetric cone conformations, while the larger cavitands (n = 6 and 7) adopt conformations of lower symmetry, H-1 NMR spectroscopic studies of [6]cavitand and [7]cavitand revealed that these hosts undergo exchange between equivalent conformations at room temperature. The departure of these two cavitands from cone conformations is related to steric crowding on their Ar-O-CH2-O-Ar bridges and is predicted by simple molecular mechanics calculations (MM2 force field). X-ray diffraction studies on single crystals of the [4]cavitand, [5]cavitand, and [6]cavitand hosts afforded additional experimental support for these conclusions.