3-nitrophenyl-calix[4]resorcinarene | 130915-20-7

• 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: 3-nitrophenyl-calix[4]resorcinarene
• 英文别名: 2,8,14,20-Tetrakis(3-nitrophenyl)pentacyclo[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: 130915-20-7；130981-67-8
• 化学式: C₅₂H₃₆N₄O₁₆
• 分子量: 972.875
• InChiKey: WMHQLMZSRYKUDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  72
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  345
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3-nitrophenyl-calix[4]resorcinarene 在 镍 、 sodium carbonate 、 一水合肼 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 N-[3-[14-[3-[benzoyl(hydroxy)amino]phenyl]-4,6,10,12,16,18,22,24-octahydroxy-8,20-bis(3-nitrophenyl)-2-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9,11,13(27),15(26),16,18,21,23-dodecaenyl]phenyl]-N-hydroxybenzamide
  参考文献：
  名称：

  Microwave‐Assisted Synthesis of Calix[4]resorcinarene Hydroxamic Acids

  摘要：

  New calix[4]resorcinarenes bearing hydroxamic acid groups, calix[4]resorcinarene hydroxamic acids (CRAHAs), have been synthesized.

  DOI：

  10.1080/00397910500498895
• 作为产物：
  描述：

  间硝基苯甲醛 、 间苯二酚 在 silica sulfuric acid 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以80%的产率得到3-nitrophenyl-calix[4]resorcinarene
  参考文献：
  名称：

  Silica Sulfuric Acid-Catalyzed Syntheses of Calix[4] Resorcinarenes

  摘要：

  二氧化硅硫酸（SSA）首次作为一种高效催化剂，通过间苯二酚与芳香醛的一锅缩合，促进了rctt构型钙并[4]间苯二酚的合成。4- cyanophenyl-calix[4]resorcinarene (3b) 的结构已通过单晶 X 射线衍射确定。

  DOI：

  10.2174/1570178611310040012

文献信息

• Host-guest chemistry. 27. Mechanisms of macrocycle genesis. The condensation of resorcinol with aldehydes
  作者：Frank Weinelt、Hans Joerg Schneider

  DOI：10.1021/jo00019a011

  日期：1991.9

  The title reactions proceed in high yields without high dilution techniques as long as substituents allow hydrogen bonds between the phenolic units and do not lead to steric hindrance. Isomerization rates for three epimeric cyclophanes, including a hitherto undiscovered one, are obtained by least-squares fit with integrated rate equations. The buildup sequences of oligomers, polymers, and macrocycles are analyzed by numerical stepwise integration with 50 rate constants, based on the fit of time-concentration curves of seven identified structures that were followed by proton NMR. Macrocyclization is favored by the following: (a) fast degradation of oligomers, (b) fast ring closure of tetramers, as well as (c) fast chain growth to these in comparison to ring opening. Homogeneous reaction conditions, here with methanol as solvent, are essential not only for the quantitative analyses, but also for the solubility of polymers in view of their degradation and for the observation of new stereoisomers. Molecular mechanics calculations with the CHARMm field and model considerations identify the factors responsible for the unique preference for cyclization over polymerization. Both hydrogen bonds between the phenolic units and 1.5 interactions between phenolic groups and the methyl substituent-stemming from the acetaldehyde-strongly favor folded conformers with small distances around d = 3.3-4.6 angstrom between the terminal reacting centers in comparison to stretched conformations with d = 12.2-18.3 angstrom.