5,11,17,23,29,35-Hexa-tert-butyl-37,38,39,41-teramethoxy-40,42-dihydroxycalix<6>arene | 154388-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17,23,29,35-Hexa-tert-butyl-37,38,39,41-teramethoxy-40,42-dihydroxycalix<6>arene
• 英文别名: 5,11,17,23,29,35-hexa-tert-butyl-37,38,39,41-tetramethoxycalix<6>arene-40,42-diol；5,11,17,23,29,35-hexa-tert-butyl-37,38,39,41-tetramethoxy-40,42-dihydroxycalix<6>arene；5,11,17,23,29,35-Hexatert-butyl-38,40,41,42-tetramethoxyheptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(36),3(42),4,6,9,11,13(41),15,17,19(40),21,23,25(39),27(38),28,30,33(37),34-octadecaene-37,39-diol
• CAS: 154388-73-5
• 化学式: C₇₀H₉₂O₆
• 分子量: 1029.5
• InChiKey: XZBMRLLAYRRXRS-UHFFFAOYSA-N

物化性质

• 沸点：
  938.2±65.0 °C(Predicted)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  20.7
• 重原子数：
  76
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,11,17,23,29,35-Hexa-tert-butyl-37,38,39,41-teramethoxy-40,42-dihydroxycalix<6>arene 、 叔丁基异氰酸酯 在 barium(II) hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.5h， 以99%的产率得到p-tert-butylcalix[6]arene-1,2,3,5-tetramethyl-3-mono-N-tert-butylaminocarbonyl
  参考文献：
  名称：

  基于多酚的分子平台的定制功能化

  摘要：

  选择性修饰大环低聚物的通用且有效的方法很少见，主要是因为难以将反应限制在一定数量的相同官能团上。这项工作描述了由多酚平台iteroselective官能一个独特的，一般情况下，合理的方法ñ -叔-butylaminocarbonyl（BAC）组。该方法包括使低聚平台与t反应-BuNCO和非极性溶剂中的无机碱。此非常简单的一步步骤已应用于各种杯[4、5、6和8]芳烃，并且在所有情况下，均以高收率（> 90％）分离了具有单个剩余酚部分的杯芳烃。有趣的是，这种所谓的“一劳永逸”的方法可以直接访问具有固有手性的杯芳烃。还显示了Bac基团可以用作保护基团。因此，仅用一种方法已用于关键前体平台的有效单功能化，说明了其用于复杂大环低聚物定制合成的巨大潜力。

  DOI：

  10.1021/jo501021c
• 作为产物：
  描述：

  1,3,5-trimethoxy-p-tert-butylcalix[6]arene 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以39%的产率得到5,11,17,23,29,35-Hexa-tert-butyl-37,38,39,41-teramethoxy-40,42-dihydroxycalix<6>arene
  参考文献：
  名称：

  Syntheses of All Possible O-Methylation Products Derivable from 5,11,17,23,29,35-Hexa-tert-butylcalix[6]arene-37,38,39,40,41,42-hexol

  摘要：

  We here report methods for the synthesis of all twelve possible 0-methylation products from 5,11,17,23,29,35-hexa-tert-butylcalix[6]arene-37,38,39,40,41,42-hexol (1): one mono-, three di-, three tri-, three tetra-, one penta-, and one hexamethylated products. The strategies used are (i) direct O-methylation with different 1/K2CO3 ratios, (ii) selective mono-O-methylation of O-alkylation products, (iii) demethylation with TiCl4 or LiI, and (iv) protection-deprotection with a benzyl group or an o- or m-xylenyl group. We believe that these O-methylation products are useful as basic skeletons to design functionalized calix[6]arenes with the desired number of substituents and regioselectively-positioned functional groups.

  DOI：

  10.1021/jo00085a048

文献信息

• Definitive Evidence for Inhibition of Calix[6]arene Ring Inversion Obtained from a 1,3-Xylenyl-Bridged Chiral Calix[6]arene
  作者：Hideyuki Otsuka、Seiji Shinkai

  DOI：10.1021/ja953626b

  日期：1996.1.1

  To design calix[6]arene-based receptor molecules which show high affinity and high selectivity toward guest molecules, the construction of more rigid and conformationally-defined analogs has been l...

  为了设计对客体分子显示出高亲和力和高选择性的基于杯[6]芳烃的受体分子，构建更刚性和构象定义的类似物已成为一项重要...
• Synthesis and NMR Spectroscopic Studies of Bridged and Capped Calix[6]arenes: High-Yield Syntheses of Unimolecular Caged Compounds from Calix[6]arene
  作者：Hideyuki Otsuka、Koji Araki、Hitoshi Matsumoto、Takaaki Harada、Seiji Shinkai

  DOI：10.1021/jo00120a033

  日期：1995.7

  Calix[6]arenes were bridged with a xylenyl unit or capped with a mesitylenyl unit, and their conformational properties were examined by spectroscopic methods. As previously reported by Gutsche et al., the calix[6]arene bridged on 1,4-phenyl units could enjoy slow ring inversion. The calix[6]arene bridged on 1,a-phenyl units also showed the ring inversion behavior, whereas in the calix[6]arene bridged on 1,3-phenyl units, ring inversion was virtually suppressed because of destabilization of the transition state. The capping of 1,3,5-tri-O-alkylated calix[6]arenes with 1,3,5-tris(bromomethyl)benzene gave the products in high yields (80-91%). This advantage was accounted for by the C-3 symmetrical complementarity of these two reactants. In these capped products, ring inversion was inhibited under the present measurement conditions, and the presence of a unimolecularly closed inner cavity was suggested on the basis of H-1 NMR spectroscopy and MM3 calculations.
• Otsuka Hideyuki, Araki Koji, Shinkai Seiji, J. Org. Chem, 59 (1994) N 6, S 1542-1547
  作者：Otsuka Hideyuki, Araki Koji, Shinkai Seiji

  DOI：——

  日期：——
• Syntheses of all poasible calix[6]arene derivatives with MeO- and ROCOCH2O- substituents and their metal binding properties
  作者：Hideyuki Otsuka、Koji Araki、Seiji Shinkai

  DOI：10.1016/0040-4020(95)00466-l

  日期：1995.8

  It has become possible to synthesize all possible calix[6]arene derivatives with MeO- and ROCOCH(2)O- substituents from corresponding O-methylated calix[6]arenes(2-7). The yields of these reactions were relatively high and the products could be easily purified because of the absence of other regioisomers. They are one mono-, three di-, three tri-, three tetra-, one penta-, and one hexa-EtOCOCH(2)O-substituted products. It was proved that O-methylation products act as useful basic skeletons to design functionalized calix[6]arenes with the desired number of ROCOCH(2)O substituents and the regioselectively-positioned ROCOCH(2)O groups.
• Syntheses of All Possible O-Methylation Products Derivable from 5,11,17,23,29,35-Hexa-tert-butylcalix[6]arene-37,38,39,40,41,42-hexol
  作者：Hideyuki Otsuka、Koji Araki、Seiji Shinkai

  DOI：10.1021/jo00085a048

  日期：1994.3

  We here report methods for the synthesis of all twelve possible 0-methylation products from 5,11,17,23,29,35-hexa-tert-butylcalix[6]arene-37,38,39,40,41,42-hexol (1): one mono-, three di-, three tri-, three tetra-, one penta-, and one hexamethylated products. The strategies used are (i) direct O-methylation with different 1/K2CO3 ratios, (ii) selective mono-O-methylation of O-alkylation products, (iii) demethylation with TiCl4 or LiI, and (iv) protection-deprotection with a benzyl group or an o- or m-xylenyl group. We believe that these O-methylation products are useful as basic skeletons to design functionalized calix[6]arenes with the desired number of substituents and regioselectively-positioned functional groups.