2,5,8,11,14,20,23,26,29,32-Decaoxa-tricyclo[31.2.2.1^15,19]octatriaconta-1(36),15,17,19(38),33(37),34-hexaene | 160750-47-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5,8,11,14,20,23,26,29,32-Decaoxa-tricyclo[31.2.2.1^15,19]octatriaconta-1(36),15,17,19(38),33(37),34-hexaene
• 英文别名: 2,5,8,11,14,20,23,26,29,32-Decaoxatricyclo[31.2.2.115,19]octatriaconta-1(36),15(38),16,18,33(37),34-hexaene；2,5,8,11,14,20,23,26,29,32-decaoxatricyclo[31.2.2.115,19]octatriaconta-1(36),15(38),16,18,33(37),34-hexaene
• CAS: 160750-47-0
• 化学式: C₂₈H₄₀O₁₀
• 分子量: 536.62
• InChiKey: KKVCCRXYBFJRCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  38
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,1''-(1,3-phenylene-bis(methylene))bis-4,4'-bipyridinium-bis(hexafluorophosphate) 、 2,5,8,11,14,20,23,26,29,32-Decaoxa-tricyclo[31.2.2.1^15,19]octatriaconta-1(36),15,17,19(38),33(37),34-hexaene 、 间二溴苄 在 ammonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、1199.99 MPa 条件下， 反应 48.0h， 以1.7%的产率得到<<2>-<1,4,7,10,13,20,23,26,29,32-decaoxa<13>para<13>metacyclophane><9,18,29,38-tetraazonia-<1>meta<1.0>para<1>meta<1.0>paracyclophane>catenane> tetrakishexafluorophosphate
  参考文献：
  名称：

  Amabilino, David B.; Anelli, Pier-Lucio; Ashton, Peter R., Journal of the American Chemical Society, 1995, vol. 117, # 45, p. 11142 - 11170

  摘要：

  DOI：
• 作为产物：
  描述：

  双[2-(2-氯化乙氧基)乙基]醚 在 四丁基碘化铵 、 sodium hydride 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 288.0h， 生成 2,5,8,11,14,20,23,26,29,32-Decaoxa-tricyclo[31.2.2.1^15,19]octatriaconta-1(36),15,17,19(38),33(37),34-hexaene
  参考文献：
  名称：

  Syntheses of Monofunctional Derivatives of m-Phenylene-16-crown-5, Bis(m-phenylene)-32-crown-10, and m-Phenylene-p-phenylene-33-crown-10

  摘要：

  A series of monofunctional bis(m-phenylene)-32-crown-10 and m-phenylene-p-phenylene-33-crown-10 derivatives has been synthesized. Cyclization of m- and p-bis(omega-chlorotetraethyleneoxy)benzenes (6) with 5-substituted resorcinols 1 using pseudo-high dilution conditions in DMF and either CsF or K2CO3 as base afforded 5-carbomethoxy-1,3-phenylene-m-phenylene-32-crown-10 (7a, 46%), 5-carbomethoxy-1,3-phenylene-p-phenylene-33-crown-10 (7b, 48%), 5-(benzyloxy)-1,3-phenylen-m-phenylene-32-crown-10 (11b, 51%). Unsubstituted m-phenylene-p-phenylene-33-crown-10 (15) was also made (29%) in this way. Functional group conversions of the bis-phenylene macrocycles yielded 5-carboxy-1,3-phenylene-m-phenylene-32-crown-10 (8a), 5-(hydroxymethyl)-1,3-phenylene-m-phenylene-32-crawn-10 (9a), 5-(bromomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (10a), 5-hydroxy-1,3-phenylene-m-phenylene-32-crown-10 (12a), 5-hydroxy-1,3-phenylene-p-phenylene-33-crown-10 (12b), 5-(phthalimidomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (13a), and 5-(aminomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (14a). Similarly 5-carbomethoxy-1,3-phenylene-16-crown-5 (4) was transformed to the corresponding acid (16), hydroxymethyl (17), formyl(18), bromomethyl (19), phthalimidomethyl (20), azidomethyl (21), and aminomethyl (22) derivatives. These compounds are building blocks for supramolecular assemblies (as shown by the synthesis of a Schiff base (23) from 18 and a diester (24) from 4,4'-biphenol and 17) and useful endcapping or pendant host components of macromolecules.

  DOI：

  10.1021/jo9619948

文献信息

• Self-assembled [2]catenanes exhibiting highly selective translational isomerism
  作者：David B. Amabilino、Peter R. Ashton、George R. Brown、Wayne Hayes、J. Fraser Stoddart、Malcolm S. Tolley、David J. Williams

  DOI：10.1039/c39940002479

  日期：——

  Template-directed synthesis is used to construct two isomeric [2]catenanes incorporating the macrocyclic polyether, (paraphenylene-metaphenylene)-33-crown- 10, and either (i) cyclobis (paraquat-p-phenylene) or (ii) cyclo(paraquat-p-phenylene)(paraquat-m-phenylene) as their tetrakis(hexafluorophosphates); these isomeric [2]catenanes are found to have a remarkable preference to exist as one translational isomer, both in the solid (by X-ray crystallography) and solution (by variable-temperature 1H NMR spectroscopy) states–the one in which a hydrouinone, rather than a resorcinol, ring is located inside the cavities of the isomeric tetracationic cyclophanes.

  模板导向合成用于构建两种异构体[2]环烷，其中包含大环聚醚（对亚苯基-间亚苯基）-33-冠-10，以及（i）环双（百草枯-对亚苯基）或（ii）环（百草枯-对-亚苯基)(百草枯-间-亚苯基)作为它们的四(六氟磷酸盐)；人们发现，这些异构体 [2] 环烷特别倾向于以一种平移异构体的形式存在，无论是在固体（通过 X 射线晶体学）还是溶液（通过变温 1H NMR 光谱）状态——其中氢醌，而不是间苯二酚，环位于异构四阳离子环烷的空腔内。
• Syntheses of Monofunctional Derivatives of <i>m</i>-Phenylene-16-crown-5, Bis(<i>m</i>-phenylene)-32-crown-10, and <i>m</i>-Phenylene-<i>p</i>-phenylene-33-crown-10
  作者：Harry W. Gibson、Devdatt S. Nagvekar、Nori Yamaguchi、Feng Wang、William S. Bryant

  DOI：10.1021/jo9619948

  日期：1997.7.1

  A series of monofunctional bis(m-phenylene)-32-crown-10 and m-phenylene-p-phenylene-33-crown-10 derivatives has been synthesized. Cyclization of m- and p-bis(omega-chlorotetraethyleneoxy)benzenes (6) with 5-substituted resorcinols 1 using pseudo-high dilution conditions in DMF and either CsF or K2CO3 as base afforded 5-carbomethoxy-1,3-phenylene-m-phenylene-32-crown-10 (7a, 46%), 5-carbomethoxy-1,3-phenylene-p-phenylene-33-crown-10 (7b, 48%), 5-(benzyloxy)-1,3-phenylen-m-phenylene-32-crown-10 (11b, 51%). Unsubstituted m-phenylene-p-phenylene-33-crown-10 (15) was also made (29%) in this way. Functional group conversions of the bis-phenylene macrocycles yielded 5-carboxy-1,3-phenylene-m-phenylene-32-crown-10 (8a), 5-(hydroxymethyl)-1,3-phenylene-m-phenylene-32-crawn-10 (9a), 5-(bromomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (10a), 5-hydroxy-1,3-phenylene-m-phenylene-32-crown-10 (12a), 5-hydroxy-1,3-phenylene-p-phenylene-33-crown-10 (12b), 5-(phthalimidomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (13a), and 5-(aminomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (14a). Similarly 5-carbomethoxy-1,3-phenylene-16-crown-5 (4) was transformed to the corresponding acid (16), hydroxymethyl (17), formyl(18), bromomethyl (19), phthalimidomethyl (20), azidomethyl (21), and aminomethyl (22) derivatives. These compounds are building blocks for supramolecular assemblies (as shown by the synthesis of a Schiff base (23) from 18 and a diester (24) from 4,4'-biphenol and 17) and useful endcapping or pendant host components of macromolecules.
• Amabilino, David B.; Anelli, Pier-Lucio; Ashton, Peter R., Journal of the American Chemical Society, 1995, vol. 117, # 45, p. 11142 - 11170
  作者：Amabilino, David B.、Anelli, Pier-Lucio、Ashton, Peter R.、Brown, George R.、Córdova, Emilio、Godínez, Luis A.、Hayes, Wayne、Kaifer, Angel E.、Philp, Douglas、Slawin, Alexandra M. Z.、Spencer, Neil、Stoddart, J. Fraser、Tolley, Malcolm S.、Williams, David J.

  DOI：——

  日期：——