5,11,17,23,29,35-Hexa-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis(benzyloxy)calix<6>arene | 140659-05-8

• 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-39,42-dihydroxy-37,38,40,41-tetrakis(benzyloxy)calix<6>arene
• 英文别名: 5,11,17,23,29,35-hexa-tert-butyl-37,38,40,41-tetrakis(benzyloxy)-39,42-dihydroxycalix<6>arene；5,11,17,23,29,35-Hexatert-butyl-38,39,41,42-tetrakis(phenylmethoxy)heptacyclo[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(39),22,24,27,29,31(38),33(37),34-octadecaene-37,40-diol
• CAS: 140659-05-8
• 化学式: C₉₄H₁₀₈O₆
• 分子量: 1333.89
• InChiKey: CAKCKFKEBJUTTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  26.7
• 重原子数：
  100
• 可旋转键数：
  18
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.36
• 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-39,42-dihydroxy-37,38,40,41-tetrakis(benzyloxy)calix<6>arene 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 5,11,17,23,29,35-Hexa-tert-butyl-39,42-dimethoxy-37,38,40,41-tetrakis(benzyloxy)calix<6>arene
  参考文献：
  名称：

  Conformational Characteristics of p-tert-Butylcalix[6]arene Ethers

  摘要：

  The conformational characteristics of a variety of O-substituted p-tert-butylcalix[6]arenes have been studied by means of the H-1 NMR patterns arising from their ArCH2Ar methylene protons and from the position of the C-13 NMR lines arising from the carbons bearing these protons. On the basis of this information, the tribenzyl trimethyl ether 13, the bis-calixarenes 15 and 16, the monobenzyl ether 3, the monobenzyl pentamethyl ether 10, and the hexakis(p-cyanobenzyl) ether 19b are established as having cone conformations at ambient temperature. The tetrabenzyl dimethyl ether 14, the tetrabenzoyl esters 17a-d, the tetraarylmethyl ethers 18a-d, and the bridged ether 21, on the other hand, are found to possess 1,2,3-alternate conformations. The conformational mobilities of these compounds were assessed by variable temperature H-1 NMR spectral measurements, leading to the classification of the structures as immobile, semimobile, or mobile with respect to conformational interconversion via the ''lower rim through the annulus'' pathway.

  DOI：

  10.1021/jo00093a019
• 作为产物：
  描述：

  4-叔丁基杯[6]芳烃 、 溴甲苯 在 sodium hydride 作用下， 生成 5,11,17,23,29,35-Hexa-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis(benzyloxy)calix<6>arene
  参考文献：
  名称：

  Calixarenes. 29. Aroylation and arylmethylation of calix[6]arenes

  摘要：

  Aroylations and arylmethylations of p-tert-butylcalix[6]arene have been carried out using a variety of parasubstituted aroyl chlorides and arylmethyl halides to determine the effect of para substituents on the structural and/or conformational outcome of the reactions. When an excess of derivatizing agent is used with NaH as the base the products in all cases are the 1,2,4,5-tetrasubstituted compounds in the 1,2,3-alternate conformation. However, with Me3SiOK as the base the products of arylmethylation are the 1,4-diethers. By varying the reaction conditions it is possible in some cases to prepare hexaethers as well as monoethers. By means of H-1 NMR spectral measurements it has been shown that any aroyl moiety or any para-substituted phenylmethyl moiety is large enough to prevent its rotation through the annulus of the calix[6]arene, thus partially, or in some cases completely, freezing the conformation. The unsubstituted benzyl moiety, however, is small enough to pass through the annulus fairly easily, thus allowing complete conformational interconversion to occur. The synthetic utility of these derivatives is adumbrated by the selective de-tert-butylation of a tetraester and the intramolecular bridging of a diether.

  DOI：

  10.1021/jo00037a037

文献信息

• Conformational Characteristics of p-tert-Butylcalix[6]arene Ethers
  作者：Suseela Kanamathareddy、C. David Gutsche

  DOI：10.1021/jo00093a019

  日期：1994.7

  The conformational characteristics of a variety of O-substituted p-tert-butylcalix[6]arenes have been studied by means of the H-1 NMR patterns arising from their ArCH2Ar methylene protons and from the position of the C-13 NMR lines arising from the carbons bearing these protons. On the basis of this information, the tribenzyl trimethyl ether 13, the bis-calixarenes 15 and 16, the monobenzyl ether 3, the monobenzyl pentamethyl ether 10, and the hexakis(p-cyanobenzyl) ether 19b are established as having cone conformations at ambient temperature. The tetrabenzyl dimethyl ether 14, the tetrabenzoyl esters 17a-d, the tetraarylmethyl ethers 18a-d, and the bridged ether 21, on the other hand, are found to possess 1,2,3-alternate conformations. The conformational mobilities of these compounds were assessed by variable temperature H-1 NMR spectral measurements, leading to the classification of the structures as immobile, semimobile, or mobile with respect to conformational interconversion via the ''lower rim through the annulus'' pathway.
• Kanamathareddy Suseela, Gutsche C. David, J. Org. Chem, 59 (1994) N 14, S 3871-3879
  作者：Kanamathareddy Suseela, Gutsche C. David

  DOI：——

  日期：——
• 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 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.
• Calixarenes. 29. Aroylation and arylmethylation of calix[6]arenes
  作者：Suseela Kanamathareddy、C. David Gutsche

  DOI：10.1021/jo00037a037

  日期：1992.5

  Aroylations and arylmethylations of p-tert-butylcalix[6]arene have been carried out using a variety of parasubstituted aroyl chlorides and arylmethyl halides to determine the effect of para substituents on the structural and/or conformational outcome of the reactions. When an excess of derivatizing agent is used with NaH as the base the products in all cases are the 1,2,4,5-tetrasubstituted compounds in the 1,2,3-alternate conformation. However, with Me3SiOK as the base the products of arylmethylation are the 1,4-diethers. By varying the reaction conditions it is possible in some cases to prepare hexaethers as well as monoethers. By means of H-1 NMR spectral measurements it has been shown that any aroyl moiety or any para-substituted phenylmethyl moiety is large enough to prevent its rotation through the annulus of the calix[6]arene, thus partially, or in some cases completely, freezing the conformation. The unsubstituted benzyl moiety, however, is small enough to pass through the annulus fairly easily, thus allowing complete conformational interconversion to occur. The synthetic utility of these derivatives is adumbrated by the selective de-tert-butylation of a tetraester and the intramolecular bridging of a diether.