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 | 137964-72-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 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
• 英文别名: 5-bromo-4(24),6(10),12(16),18(22)-tetramethylenedioxy-2,8,14,20-tetrapentylresorcin[4]arene；25,29,33,37-Tetrapentyl-2,4,8,10,14,16,20,22-octaoxanonacyclo[21.15.1.124,38.05,36.07,34.011,32.013,30.017,28.019,26]tetraconta-1(39),5,7(34),11,13(30),17(28),18,23,26,31,35,38(40)-dodecaene
• CAS: 137964-72-8
• 化学式: C₅₂H₆₄O₈
• 分子量: 817.075
• InChiKey: XSTMNHBQTNKFNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.9
• 重原子数：
  60
• 可旋转键数：
  16
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  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 在 仲丁基锂 、 硼酸三甲酯 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 19.5h， 生成 tetrahydroxy cavitand
  参考文献：
  名称：

  阴离子与基于间苯二甲烯的空洞结合：CH ...阴离子相互作用的重要性。

  摘要：

  DOI：

  10.1002/anie.200703451
• 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

• Hexacarboxylic Acid Biscavitands
  作者：Linda Gutierrez-Tunstad、Gang Zhao、Peter Castro

  DOI：10.1055/s-2004-834834

  日期：——

  The synthesis of hexacarboxylic acid biscavitands is described. These new singly bridged biscavitands are based on resorcin[4]arene with a flexible all-carbon bridge at one 2-resorcyl position and carboxylic acids at the remaining 2-resorcyl positions. Preliminary self-assembling behavior of these new biscavitands is described.

  文中介绍了六羧酸双穴醚的合成。这些新型单桥连双穴醚以间苯二酚[4]芳烃为基底，在其中一个2-间苯甲酰位置上具有一个灵活的全碳桥，而在其余的2-间苯甲酰位置上则带有羧酸基团。初步描述了这些新型双穴醚的自组装行为。
• Resorcinarenyl‐Phosphines in Suzuki–Miyaura Cross‐Coupling Reactions of Aryl Chlorides
  作者：Laure Monnereau、Hani El Moll、David Sémeril、Dominique Matt、Loïc Toupet

  DOI：10.1002/ejic.201301473

  日期：2014.3

  AbstractTwo phosphines built on a bowl‐shaped resorcin[4]arene skeleton, namely 5‐diphenylphosphanyl‐ and 5‐diisopropylphosphanyl‐4(24),6(10),12(16),18(22)‐tetramethylenedioxy‐2,8,14,20‐tetrapentylresorcin[4]arene, have been synthesised and tested in the Suzuki–Miyaura cross‐coupling reaction of aryl halides. Combining these ligands with [Pd(OAc)2] resulted in highly active catalysts that allowed the formation of o,o′‐biphenyls starting from aryl chlorides. The remarkable activities observed possibly arise from 1) the capacity of the phosphines to operate transiently as P,O chelators, thereby increasing the electron density of the metal, and 2) the ability of the ligands to embed metal–organic units, which, when occurring, makes the ligand considerably bulkier so as to disfavour the coordination of a second phosphine. Both features are known to facilitate the oxidative addition step.