11'-(tert-butyl)-5',17',23',37',40',42'45',47'-octamethyldispiro[cyclohexane-1,2'-[7,15,25,35]tetraazaheptacyclo[34.2.2.2(3,6).2(16,19).2(21,24).1(9,13).1(28,32)]octatetraconta[3,5,9,11,13(46),16,18,21,23,28,30,32(41),36,38,39,42,44,47]octadecaene...].. | 231613-66-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 11'-(tert-butyl)-5',17',23',37',40',42'45',47'-octamethyldispiro[cyclohexane-1,2'-[7,15,25,35]tetraazaheptacyclo[34.2.2.2(3,6).2(16,19).2(21,24).1(9,13).1(28,32)]octatetraconta[3,5,9,11,13(46),16,18,21,23,28,30,32(41),36,38,39,42,44,47]octadecaene...]..
• CAS: 231613-66-4
• 化学式: C₆₆H₇₆N₄O₄
• 分子量: 989.354
• InChiKey: YVCMXVBWQBBNFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.2
• 重原子数：
  74
• 可旋转键数：
  1
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氯磺酰苯甲酰氯 、 4-[tris(4-tert-butylphenyl)methyl]aniline 、 11'-(tert-butyl)-5',17',23',37',40',42'45',47'-octamethyldispiro[cyclohexane-1,2'-[7,15,25,35]tetraazaheptacyclo[34.2.2.2(3,6).2(16,19).2(21,24).1(9,13).1(28,32)]octatetraconta[3,5,9,11,13(46),16,18,21,23,28,30,32(41),36,38,39,42,44,47]octadecaene...].. 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以7%的产率得到[2]{N-{4-{tris[4-(tert-butyl)phenyl]methyl}phenyl}-3-{{{4-{tris[4-(tert-butyl)phenyl]methyl}phenyl}amino}sulfonyl}benzamide}-{11'(tert-butyl)-5',17',23',37',40',42',45',47'-octamethyldispiro[cyclohexane-1,2'-[7,15,25,35]tetraazaheptacyclo...]}...
  参考文献：
  名称：

  Size Complementarity of Macrocyclic Cavities and Stoppers in Amide-Rotaxanes

  摘要：

  New [2]rotaxanes were prepared by the threading and the slipping procedure, the latter having the advantage of not needing templating interactions. As a consequence, the first [2]rotaxane consisting of a tetraamide macrocycle and a pure hydrocarbon thread was synthesized (see 12a in Scheme 2). Sterically matching wheels and axles being the basic requirement of a successful slipping approach to rotaxanes, mono- and bishomologous wheels 5b, c with larger diameters than the parent 5a were synthesized and mechanically connected to amide axles 10a-c which were stoppered with blocking groups of different spatial demand (Scheme 1). The deslipping kinetics of the resulting rotaxanes 8a-c and 9a,b were measured and compared; it emerges that even slight increases in the wheel size require larger stoppers to stabilize the mechanical bond. Moreover, when the deslipping rate of 8a (amide wheel and amide axle) was determined in either DMF or THF, a strong dependence on the solvent polarity, which is caused by a differing extent of intramolecular H-bonds between the wheel and the axle, was observed. As expected, no such dependence was detected for rotaxane 12a (amide wheel and hydrocarbon axle) whose components cannot interact via ii-bonds. The comparison of the sterically matching pairs of macrocycles and blocking groups, found by a systematic fitting based on the results of slipping and deslipping experiments, with other rotaxane types bearing similar stoppers allows conclusions concerning the relative cavity size of wheels of various structure.

  DOI：

  10.1002/(sici)1522-2675(19990505)82:5<746::aid-hlca746>3.0.co;2-c
• 作为产物：
  描述：

  5-tert-butylisophthaloyl dichloride 、 N,N'-bis{4-[-(4-amino-3,5-dimethylphenyl)cyclohexyl]-2,6-dimethylphenyl}benzene-1,3-diacetamide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以57%的产率得到11'-(tert-butyl)-5',17',23',37',40',42'45',47'-octamethyldispiro[cyclohexane-1,2'-[7,15,25,35]tetraazaheptacyclo[34.2.2.2(3,6).2(16,19).2(21,24).1(9,13).1(28,32)]octatetraconta[3,5,9,11,13(46),16,18,21,23,28,30,32(41),36,38,39,42,44,47]octadecaene...]..
  参考文献：
  名称：

  Size Complementarity of Macrocyclic Cavities and Stoppers in Amide-Rotaxanes

  摘要：

  New [2]rotaxanes were prepared by the threading and the slipping procedure, the latter having the advantage of not needing templating interactions. As a consequence, the first [2]rotaxane consisting of a tetraamide macrocycle and a pure hydrocarbon thread was synthesized (see 12a in Scheme 2). Sterically matching wheels and axles being the basic requirement of a successful slipping approach to rotaxanes, mono- and bishomologous wheels 5b, c with larger diameters than the parent 5a were synthesized and mechanically connected to amide axles 10a-c which were stoppered with blocking groups of different spatial demand (Scheme 1). The deslipping kinetics of the resulting rotaxanes 8a-c and 9a,b were measured and compared; it emerges that even slight increases in the wheel size require larger stoppers to stabilize the mechanical bond. Moreover, when the deslipping rate of 8a (amide wheel and amide axle) was determined in either DMF or THF, a strong dependence on the solvent polarity, which is caused by a differing extent of intramolecular H-bonds between the wheel and the axle, was observed. As expected, no such dependence was detected for rotaxane 12a (amide wheel and hydrocarbon axle) whose components cannot interact via ii-bonds. The comparison of the sterically matching pairs of macrocycles and blocking groups, found by a systematic fitting based on the results of slipping and deslipping experiments, with other rotaxane types bearing similar stoppers allows conclusions concerning the relative cavity size of wheels of various structure.

  DOI：

  10.1002/(sici)1522-2675(19990505)82:5<746::aid-hlca746>3.0.co;2-c

文献信息

• Size Complementarity of Macrocyclic Cavities and Stoppers in Amide-Rotaxanes
  作者：Christiane Heim、Ansgar Affeld、Martin Nieger、Fritz Vögtle

  DOI：10.1002/(sici)1522-2675(19990505)82:5<746::aid-hlca746>3.0.co;2-c

  日期：1999.5.5

  New [2]rotaxanes were prepared by the threading and the slipping procedure, the latter having the advantage of not needing templating interactions. As a consequence, the first [2]rotaxane consisting of a tetraamide macrocycle and a pure hydrocarbon thread was synthesized (see 12a in Scheme 2). Sterically matching wheels and axles being the basic requirement of a successful slipping approach to rotaxanes, mono- and bishomologous wheels 5b, c with larger diameters than the parent 5a were synthesized and mechanically connected to amide axles 10a-c which were stoppered with blocking groups of different spatial demand (Scheme 1). The deslipping kinetics of the resulting rotaxanes 8a-c and 9a,b were measured and compared; it emerges that even slight increases in the wheel size require larger stoppers to stabilize the mechanical bond. Moreover, when the deslipping rate of 8a (amide wheel and amide axle) was determined in either DMF or THF, a strong dependence on the solvent polarity, which is caused by a differing extent of intramolecular H-bonds between the wheel and the axle, was observed. As expected, no such dependence was detected for rotaxane 12a (amide wheel and hydrocarbon axle) whose components cannot interact via ii-bonds. The comparison of the sterically matching pairs of macrocycles and blocking groups, found by a systematic fitting based on the results of slipping and deslipping experiments, with other rotaxane types bearing similar stoppers allows conclusions concerning the relative cavity size of wheels of various structure.