16,18,19,26-Tetrapentyl-2,14-(methano<1,3>benzenomethano)-16H,18H-benzo<1,2-d:5,4-d'>bis<1,3>benzodioxocin-3,13,23,25-tetrol | 137964-70-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 16,18,19,26-Tetrapentyl-2,14-(methano<1,3>benzenomethano)-16H,18H-benzo<1,2-d:5,4-d'>bis<1,3>benzodioxocin-3,13,23,25-tetrol
• 英文别名: 16,18,19,26-Tetrapentyl-2,14-(methano[1,3]benzenomethano)-16H,18H-benzo[1,2-d:5,4-d']bis[1,3]benzodioxocin-3,13,23,25-tetrol
• CAS: 137964-70-6
• 化学式: C₅₀H₆₄O₈
• 分子量: 793.053
• InChiKey: DBUFAWKPUJNIIA-WKKVWOBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.13
• 重原子数：
  58.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  117.84
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,3-二氯喹喔啉 、 16,18,19,26-Tetrapentyl-2,14-(methano<1,3>benzenomethano)-16H,18H-benzo<1,2-d:5,4-d'>bis<1,3>benzodioxocin-3,13,23,25-tetrol 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以18%的产率得到5,7,9,30-Tetrapentyl-3,11-methano-5H,7H,9H-benzo<5,6><1,3>benzodioxocino<5'',4'':8',9'><1,3>benzodioxocino<5',4':9,10><1,4>benzodioxocino<2,3-b>quinoxaline-2,12-diol*Methanol
  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