20,22,24,25-Tetrapentyl-2,18-methano-20H,22H,24H-dibenzo<1,3>dioxocino<5,4-i:7,8-i'>bis<1,3>benzodioxocin-3,17-diol | 137964-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 20,22,24,25-Tetrapentyl-2,18-methano-20H,22H,24H-dibenzo<1,3>dioxocino<5,4-i:7,8-i'>bis<1,3>benzodioxocin-3,17-diol
• 英文别名: 20,22,24,25-Tetrapentyl-2,18-methano-20H,22H,24H-dibenzo[d,d'][1,3]dioxocino[5,4-i:7,8-i']bis[1,3]benzodioxocin-3,17-diol
• CAS: 137964-71-7
• 化学式: C₅₁H₆₄O₈
• 分子量: 805.064
• InChiKey: SMFBJAFLVWYQEV-WDEUUBJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.45
• 重原子数：
  59.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  95.84
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,3,7,8-tetrachloro-pyrazino[2,3-g]quinoxaline 、 20,22,24,25-Tetrapentyl-2,18-methano-20H,22H,24H-dibenzo<1,3>dioxocino<5,4-i:7,8-i'>bis<1,3>benzodioxocin-3,17-diol 在 sodium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以16%的产率得到
  参考文献：
  名称：

  Host-guest complexation. 61. C- and Z-shaped ditopic cavitands, their binding characteristics, and monotopic relatives

  摘要：

  Readily available octol 1, when treated with 3 mol of CH2ClBr, gave hexol 2 (3%), tetrol 3 (7%), diol 4 (17%), and tetra-bridged 5 (10%). The tetrol and diol served as starting materials for preparing mixed-bridged systems. Diol 4 reacted with 2,3-dichloroquinoxaline (7) to give 7% of cavitand 8, whereas tetrol 3 reacted with only one of the 2 mol of quinoxaline 7 to give the chiral diol 9 (18%). When 2 mol of diol 4 were treated with 1 mol of fluoranil (6), the mixture of 42% of Z-shaped 10 (Z-10) and 12% of C-shaped 10 (C-10) produced was easily separated. The crystal structures of 4.CHCl3.H2O, C-10.3CH3CN.CH2Cl2, Z-10.4CH3CO2CH2CH3, Z-10.4CH3COCH2CH3, and Z-10.6C6H5NO2 were determined and found to resemble what was predicted from molecular model examination. When 1 mol of diol 4 was mixed with tetrachlorotetraazaanthracene 12, a 16% yield of what is probably Z-11 was obtained. One-to-one association constants of C-10 in CD2Cl2 at 21-degrees-C were determined by H-1 NMR titrations with guests as follows: C6D5NO2 (K(a) = 0.6 M-1), C6D5CD3 (K(a) = 1.8 M-1), p-CD3C6D4CD3 (K(a) = 1.6), and CH3COCH2CH3 (K(a) = 1.2 M-1). Attempts to detect binding failed with 2-butyne, 2-pentyne, and methylcyclohexane, although molecular model examination suggested that all seven of the above guests are complementary to the highly preorganized ditopic cavity of C-10.

  DOI：

  10.1021/jo00028a025
• 作为产物：
  描述：

  溴氯甲烷 、 四-正-戊基怀[4]间苯二酚芳烃 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以10%的产率得到1,21,23,25-Tetrapentyl-2,20:3,19-dimetheno-1H,21H,23H,25H-bis<1,3>dioxocino<5,4-i:5',4'-i'>benzo<1,2-d:5,4-d'>bis<1,3>benzodioxocin
  参考文献：
  名称：

  Host-guest complexation. 61. C- and Z-shaped ditopic cavitands, their binding characteristics, and monotopic relatives

  摘要：

  Readily available octol 1, when treated with 3 mol of CH2ClBr, gave hexol 2 (3%), tetrol 3 (7%), diol 4 (17%), and tetra-bridged 5 (10%). The tetrol and diol served as starting materials for preparing mixed-bridged systems. Diol 4 reacted with 2,3-dichloroquinoxaline (7) to give 7% of cavitand 8, whereas tetrol 3 reacted with only one of the 2 mol of quinoxaline 7 to give the chiral diol 9 (18%). When 2 mol of diol 4 were treated with 1 mol of fluoranil (6), the mixture of 42% of Z-shaped 10 (Z-10) and 12% of C-shaped 10 (C-10) produced was easily separated. The crystal structures of 4.CHCl3.H2O, C-10.3CH3CN.CH2Cl2, Z-10.4CH3CO2CH2CH3, Z-10.4CH3COCH2CH3, and Z-10.6C6H5NO2 were determined and found to resemble what was predicted from molecular model examination. When 1 mol of diol 4 was mixed with tetrachlorotetraazaanthracene 12, a 16% yield of what is probably Z-11 was obtained. One-to-one association constants of C-10 in CD2Cl2 at 21-degrees-C were determined by H-1 NMR titrations with guests as follows: C6D5NO2 (K(a) = 0.6 M-1), C6D5CD3 (K(a) = 1.8 M-1), p-CD3C6D4CD3 (K(a) = 1.6), and CH3COCH2CH3 (K(a) = 1.2 M-1). Attempts to detect binding failed with 2-butyne, 2-pentyne, and methylcyclohexane, although molecular model examination suggested that all seven of the above guests are complementary to the highly preorganized ditopic cavity of C-10.

  DOI：

  10.1021/jo00028a025

文献信息

• Hinged Molecular Capsules:  Synthesis and Conformational Control via Temperature, pH, or Solvent Composition
  作者：Sang-Woo Kang、Peter P. Castro、Gang Zhao、Jose E. Nuñez、Carlos E. Godinez、Linda M. Gutierrez-Tunstad

  DOI：10.1021/jo0521807

  日期：2006.2.1

  Three new covalently linked molecular capsules were synthesized from their resorcinarene cavitand precursors in good yields. The capsules undergo reversible conformational switching between the closed "vase" form and the open "kite" form upon temperature or pH variation. The kite conformation obtained via either method in CDCl(3) switches to vase conformation upon addition of polar solvents such as acetone-d(6) or THF-d(8).