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 | 135269-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 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
• 英文别名: 15,35,55,75-Tetrabromo-2,4,6,8-tetramethyl-1,3,5,7(1,3)-tetrabenzenacyclooctaphan-14,16,34,36,54,56,74,76-octaol；5,11,17,23-tetrabromo-2,8,14,20-tetramethylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol
• CAS: 135269-76-0
• 化学式: C₃₂H₂₈Br₄O₈
• 分子量: 860.186
• InChiKey: GIKSBRYWPGDNPF-UHFFFAOYSA-N

物化性质

• 熔点：
  230-232 °C
• 沸点：
  502.3±50.0 °C(Predicted)
• 密度：
  1.852±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  44
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  162
• 氢给体数：
  8
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  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 在 三氯化磷 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以69%的产率得到6,12,18,39-Tetrabromo-3,9,15,21-tetrachloro-25,29,33,37-tetramethyl-2,4,8,10,14,16,20,22-octaoxa-3,9,15,21-tetraphosphanonacyclo[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
  参考文献：
  名称：

  四（O，O-磷）-桥杯[4]间苯二酚及其衍生物的合成，结构和反应活性

  摘要：

  描述了反应性四（O，O-磷）-桥杯[ 4 ]间苯二酚3和4的合成和表征。由于其在常见有机溶剂中的溶解度较差，因此进行了3（1 H，13 C，31 P）的固态NMR研究。的反应3与MeMgl中，Me 3 SiMNe 2，和HNME 2提供的η 3 γ 3 P-取代的cavitands 5和6。6与（H 2 N）的氧化加成反应2 C（= O）/ H 2 ö 2（1：1）加合物，四氯-邻苯醌（TOB），和六氟丙酮（HFA）导致了η 4 γ 5 P衍生物7，并以η 5 γ 5 P导数8和9。进行了四（O，O-磷）-桥杯[4]间苯二酚4的X射线晶体结构测定。框架显示圆锥构象；氯原子被引导向内。

  DOI：

  10.1002/cber.19971301124
• 作为产物：
  描述：

  Calix[4]resorcinarene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 丁酮 为溶剂， 反应 4.0h， 以80%的产率得到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
  参考文献：
  名称：

  Host-guest complexation. 46. Cavitands as open molecular vessels form solvates

  摘要：

  DOI：

  10.1021/ja00215a037

文献信息

• Jacopozzi, Paola; Dalcanale, Enrico; Spera, Silvia, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 3, p. 671 - 677
  作者：Jacopozzi, Paola、Dalcanale, Enrico、Spera, Silvia、Chrisstoffels, Lysander A. J.、Reinhoudt, David N.、Lippmann, Tino、Mann, Gerhard

  DOI：——

  日期：——
• Neda, Ion; Siedentop, Tjark; Vollbrecht, Alexander, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1998, vol. 53, # 8, p. 841 - 848
  作者：Neda, Ion、Siedentop, Tjark、Vollbrecht, Alexander、Thoennessen, Holger、Jones, Peter G.、Schmutzler, Reinhard

  DOI：——

  日期：——
• Synthesis and conformational dynamics of ortho-xylyl-bridged-[4]cavitands
  作者：Christoph Naumann、Brian O Patrick、John C Sherman

  DOI：10.1016/s0040-4020(01)01105-x

  日期：2002.1

  ortho-Xylyl-[4]cavitands 2 to 6 were synthesized from bromoresorcin[4] arenes 1. Cavitands 2 to 6 show C-4nu symmetry in their H-1 NMR spectra at higher temperatures. Dynamic H-1 NMR studies of 2 to 6 indicate the C-4nu symmetry is due to fast interconversion of rectangular C-2nu isomers. This is supported by the crystal structure of 2a, which shows a C-2nu rectangular structure. The activation energy barriers for 2a and 2b were measured by quantitative 1D NOESY (EXSY) experiments. The results were analyzed by the initial rate approximation and matrix calculations. The activation energy barrier was found to depend strongly on the size of the upper rim group (Br, H, OH, CN). In addition, replacing the phenolic proton of tetrol derivatives 4a and 4b with metal ions raises the energy barrier further, likely via bridging metal cations. The two tetrabromo compounds (2a and 2b) reveal a sensitivity of the activation barrier to the feet of the cavitands. Cavitand 6 may act as a hub for radially expanded cavitands. The advantages of the 1D NOESY experiments over the more commonly used two-dimensional experiments are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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
• Cavitands: synthetic molecular vessels
  作者：John R. Moran、Stefan Karbach、Donald J. Cram

  DOI：10.1021/ja00385a064

  日期：1982.10