7,11,15,28-tetrabromo-1,21,23,25-tetramethyl-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 | 83136-20-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 7,11,15,28-tetrabromo-1,21,23,25-tetramethyl-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: 6,12,18,39-Tetrabromo-25,29,33,37-tetramethyl-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: 83136-20-3
• 化学式: C₃₆H₂₈Br₄O₈
• 分子量: 908.23
• InChiKey: PHTUXLXOSDUOCV-UHFFFAOYSA-N

物化性质

• 密度：
  1.741±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  48
• 可旋转键数：
  0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  7,11,15,28-tetrabromo-1,21,23,25-tetramethyl-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 sodium hydroxide 、 正丁基锂 、 硼酸三甲酯 、 双氧水 作用下， 生成 1,21,23,25-Tetramethyl-2,20:3,19-dimetheno-1H,21H,23H,25H-bis[1,3]dioxocino[5,4-i:5'-i']benzo[1,2-d:5,4-d']bis[1,3]benzodioxocin-7,11,15,28-tetrol
  参考文献：
  名称：

  An Asymmetric Carceplex and New Crystal Structure Yield Information Regarding a 1 Million-Fold Template Effect

  摘要：

  We report the incorporation of methyl ''feet'' as pendant groups in cavitands and carceplexes and their use in the creation of an asymmetric carceplex and the facilitation of the determination of the crystal structure of a carceplex. From the asymmetric carceplex, we have determined a 19 kcal/mol energy barrier to rotation of the guest pyrazine about the host's pseudo-C-2 axes, which demonstrates a high degree of complementarity between the shell of the carceplex and the guest pyrazine. The crystal structure reveals the extensive conjugation of the aryl ethers into the aromatic rings of the host when pyrazine is the guest. This result helps explain why pyrazine is, to date, the best template for the reaction to form the carceplex and thus provides insight to the powerful template effect that is the hallmark of this carceplex reaction. Thus, the investigation of this template effect provides a sensitive probe into noncovalent interactions in general and may be useful in the understanding of recognition in both natural systems such as enzyme/substrate complexes and in non-natural systems such as designed self-assembling structures.

  DOI：

  10.1021/jo00110a025
• 作为产物：
  描述：

  溴氯甲烷 、 5,11,17,23-tetrabromo-2,8,14,20-tetramethylpentacyclo[19.3.1.1^3,7.1^9,13.1^15,19]octacosa-1-(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaen-4,6,10,12,16,18,22,24-octol 以42%的产率得到7,11,15,28-tetrabromo-1,21,23,25-tetramethyl-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：

  Cavitands: synthetic molecular vessels

  摘要：

  DOI：

  10.1021/ja00385a064

文献信息

• Efficient Coupling of Amino Acid Derivatives to Rigid Organic Scaffolds: Model Syntheses for De Novo Proteins.
  作者：Bruce C. Gibb、Adam R. Mezo、Ashley S. Causton、Janet R. Fraser、Frank C.S. Tsai、John C. Sherman

  DOI：10.1016/0040-4020(95)00485-q

  日期：1995.8

  We describe the coupling of amino acid derivatives to four different rigid organic macrocycles. The couplings were achieved in high yields, which augurs well for the coupling of polypeptides to the rigid macrocycles to create a new family of de novo proteins. We discuss the structure of the model compounds based on the hydrogen bonding patterns that are evident from their NMR and IR spectra.
• Host-guest complexation. 46. Cavitands as open molecular vessels form solvates
  作者：Donald J. Cram、Stefan. Karbach、Hye Eun. Kim、Carolyn B. Knobler、Emily F. Maverick、John L. Ericson、Roger C. Helgeson

  DOI：10.1021/ja00215a037

  日期：1988.3
• IMPROVED SYNTHESIS AND PURIFICATION OF CAVITANDS
  作者：Jorden P. Kass、Leslie A. Slasor、Cesar H. Zambrano、Eric E. Dueno

  DOI：10.1080/00304940609356441

  日期：2006.10
• Reversible Molecular Capsules Composed of Two Cavitands Linked via an Assortment of Charged-Hydrogen Bonds and Covalent Bonds
  作者：Robert G. Chapman、John C. Sherman

  DOI：10.1021/ja981596h

  日期：1998.9.1

  Six new cavitand bowls are reported (6, 7, 8, 9, 11, and 12), as are three bis-bowl compounds (4, 13, and 14). Eight new complexes (4.guest, 7C.guest, 8C.guest, 9C.guest, 14.guest, 15.guest, 15C.guest, and 16C.guest) that reversibly encapsulate small molecules are reported. Two or more charged-hydrogen bonds (CHBs) or covalent linkages between the bowls are required to form stable complexes. Guest exchange rates vary from milliseconds to days. Thermodynamically, these complexes display an enthalpy-entropy compensation. The relative stability of complex 3.pyrazine versus complex 3.chloroform is 170000 in nitrobenzene-d(5) at 298 It. Apparent stability constants in nitrobenzene-d(5) at 298 K yield 1.1 x 10(9) M-1 for complex 3.pyrazine. The absolute stability constant for complex 4.pyrazine in nitrobenzene-d(5) at 333 K is 3.5 x 10(6) M-1.
• Improved Synthesis of Cavitands
  作者：Esteban Román、Carlos Peinador、Sandra Mendoza、Angel E. Kaifer

  DOI：10.1021/jo982218y

  日期：1999.4.1