2,8,14,20-tetraphenylpentacyclo<19.3.1.13,7.19,13.115,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol | 1005763-70-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,8,14,20-tetraphenylpentacyclo<19.3.1.13,7.19,13.115,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol
• 英文别名: 2,8,14,20-tetraphenylpentacyclo<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-dodecaene-4,6,10,12,16,18,22,24-octol
• CAS: 1005763-70-1
• 化学式: C₅₂H₄₀O₈
• 分子量: 792.885
• InChiKey: LIPYULCVZHIINA-QXYIQSCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.37
• 重原子数：
  60.0
• 可旋转键数：
  4.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  161.84
• 氢给体数：
  8.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  苯甲醛 、 间苯二酚 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以10%的产率得到2,8,14,20-tetraphenylpentacyclo<19.3.1.13,7.19,13.115,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol
  参考文献：
  名称：

  Host-guest complexation. 48. Octol building blocks for cavitands and carcerands

  摘要：

  DOI：

  10.1021/jo00267a015

文献信息

• Lanthanide(III) nitrobenzenesulfonates and p-toluenesulfonate complexes of lanthanide(III), iron(III), and copper(II) as novel catalysts for the formation of calix[4]resorcinarene
  作者：Karen Deleersnyder、Hasan Mehdi、István T. Horváth、Koen Binnemans、Tatjana N. Parac-Vogt

  DOI：10.1016/j.tet.2007.06.090

  日期：2007.9

  catalysts for the synthesis of resorcinol-derived calix[4]resorcinarenes. The reaction of resorcinol with benzaldehyde yields two isomers, the all-cis isomer (rccc) and the cis-trans-trans isomer (rctt) with the relative isomer ratios depending on the reaction conditions. However, in the reaction of resorcinol with octanal only one isomer, the all-cis isomer, is formed in high yields with less than 0

  对甲苯磺酸[甲苯磺酸镧系元素甲苯磺酸盐，Ln（TOS）3 ]和硝基苯磺酸[Ln（NBSA）3 ]的镧系元素（III）盐，以及铁（III）和铜（II）的对甲苯磺酸盐络合物为制备，表征并检查了间苯二酚衍生的杯[4]间苯二芳烃的合成催化剂。间苯二酚与苯甲醛的反应产生两种异构体，即全顺式异构体（rccc）和顺式-反式-反式-异构体（rctt），其相对异构体比例取决于反应条件。然而，在间苯二酚与辛醛的反应中，仅以小于0.1mol％的Yb（TOS）3的高收率形成了一种异构体，即全顺式异构体。。对甲苯磺酸镧系元素（III）和硝基苯磺酸镧系元素（III）的检测表明，4-（III）4-硝基苯磺酸盐[no（III）甲苯磺酸盐，Yb（4-NBSA）3 ]和（III）2,4-二硝基苯磺酸盐[Yb（ 2,4-NBSA）3 ]是最具活性的催化剂。催化剂可以容易地回收并多次重复使用以形成间苯二甲烯，而不会降低效率。用对
• Bismuth compounds in organic synthesis. Synthesis of resorcinarenes using bismuth triflate
  作者：Katherine E Peterson、Russell C Smith、Ram S Mohan

  DOI：10.1016/j.tetlet.2003.08.093

  日期：2003.10

  Bismuth triflate (5 mol%) smoothly catalyzes the condensation of aromatic and aliphatic aldehydes with resorcinol to give tetrameric cyclic products, resorcinarenes. With benzaldehyde, the product is obtained as a mixture of two diastereomers and the ratio of the diastereomers depends on reaction time. On the other hand, a single diastereomer is obtained with aliphatic aldehydes. The low toxicity and

  三氟甲磺酸铋（5 mol％）平稳地催化芳香族和脂肪族醛与间苯二酚的缩合，生成四聚体环状产物间苯二芳烃。与苯甲醛一起，以两种非对映异构体的混合物形式获得产物，并且非对映异构体的比例取决于反应时间。另一方面，单一的非对映异构体与脂族醛一起获得。铋化合物的低毒性和易处理性以及快速的反应时间使该方法成为现有的间苯二甲烯形成方法的有吸引力的替代方法。
• Molecular iodine: An efficient and environment-friendly catalyst for the synthesis of calix[4]resorcinarenes
  作者：Fatemeh Darvish、Shima Khazraee

  DOI：10.1016/j.crci.2013.10.017

  日期：2014.9

  Abstract Iodine catalyzes the cyclocondensation of various aldehydes with resorcinol to give tetrameric cyclic products, resorcinarenes. Through the reaction of resorcinol with aromatic aldehydes, the product is obtained as a mixture of two isomers, the all- cis isomer (rccc) and the cis - trans - trans isomer (rctt), whereas a single diastereomer, the all- cis , is formed with aliphatic aldehydes. Besides

  摘要 碘催化各种醛与间苯二酚的环缩合反应生成四聚环状产物间苯二酚。通过间苯二酚与芳香醛的反应，得到的产物是两种异构体的混合物，全顺式异构体 (rccc) 和顺反式异构体 (rctt)，而单一的非对映异构体全顺式、由脂肪醛形成。除了出色的分离产率外，碘的使用使该过程简单、方便、经济高效且实用。
• Barrett, Anthony G. M.; Braddock, D. Christopher; Henschke, Julian P., Journal of the Chemical Society. Perkin transactions I, 1999, # 8, p. 873 - 878
  作者：Barrett, Anthony G. M.、Braddock, D. Christopher、Henschke, Julian P.、Walker, Edward R.

  DOI：——

  日期：——
• A reactive and environmentally friendly protocol for expeditious synthesis of various resorcinarenes using zinc hydrogen sulfate
  作者：Arash Mouradzadegun、Mohammad Reza Ganjali、Neda Kheirandish、Fatemeh Abadast

  DOI：10.1080/10610278.2019.1598557

  日期：2019.6.3

  In this work, for the first time, metal hydrogen phosphates and sulfates have been studied as effective solid acid catalysts for the condensation of resorcinol with aromatic and aliphatic aldehydes to give tetrameric cyclic products, resorcinarenes, which have major roles in biological and industrial activities. This catalyst has several advantages, it is non-toxic, thermally and mechanically stable, inexpensive and highly resistant against organic solvents. It increases the reaction rate about six fold and makes this method an attractive alternative to the existing methods for resorcinarene formation. Interestingly, the present catalyst exhibited a high turnover number (TON) and turnover frequency (TOF) which were even comparable with that of HCl.[GRAPHICS].