5,11,17,23,29,35-Hexa-tert-butyl-37-(benzyloxy)-38,39,40,41,42-pentamethoxycalix<6>arene | 153855-61-9

• 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-(benzyloxy)-38,39,40,41,42-pentamethoxycalix<6>arene
• 英文别名: 37-benzyloxy-5,11,17,23,29,35-hexa-tert-butyl-38,39,40,41,42-pentamethoxycalix<6>arene；5,11,17,23,29,35-Hexatert-butyl-37,38,39,40,41-pentamethoxy-42-phenylmethoxyheptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(36),3,5,7(42),9,11,13(41),15,17,19(40),21(39),22,24,27(38),28,30,33(37),34-octadecaene
• CAS: 153855-61-9
• 化学式: C₇₈H₁₀₀O₆
• 分子量: 1133.65
• InChiKey: AQZFISBIQADMMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.9
• 重原子数：
  84
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 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-(benzyloxy)-38,39,40,41,42-pentamethoxycalix<6>arene 在 palladium on activated charcoal 、 氢气 、 silver perchlorate 、 phenyltrimethylammonium tribromide 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 氯仿 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Nucleophilic Functionalization of the Calix[6]arene Para- and Meta-Position via p-Bromodienone Route

  摘要：

  It is here demonstrated that the p-bromodienone route, previously reported for calix[4] arenes, is also effective for the functionalization of the calix[6]arene macrocycle. Thus, alcoholic O-nucleophiles can be introduced at the calix[6]arene exo rim. In addition, the reaction of a calix[6]arene p-bromodienone derivative with an actived aromatic substrate, such as resorcinol, led to the first example of a meta-functionalized, inherently chiral calix[6] arene derivative.

  DOI：

  10.1021/acs.joc.5b00978
• 作为产物：
  描述：

  37-benzyloxy-5,11,17,23,29,35-hexa-tert-butyl-38,39,40,41,42-pentahydroxycalix[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， 以84%的产率得到5,11,17,23,29,35-Hexa-tert-butyl-37-(benzyloxy)-38,39,40,41,42-pentamethoxycalix<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

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.
• De Mendoza; Carramolino; Cuevas, Synthesis, 1994, # 1, p. 47 - 50
  作者：De Mendoza、Carramolino、Cuevas、Nieto、Prados、Reinhoudt、Verboom、Ungaro、Casnati

  DOI：——

  日期：——
• 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：——
• Nucleophilic Functionalization of the Calix[6]arene <i>Para</i>- and <i>Meta</i>-Position via <i>p</i>-Bromodienone Route
  作者：Margherita De Rosa、Annunziata Soriente、Gerardo Concilio、Carmen Talotta、Carmine Gaeta、Placido Neri

  DOI：10.1021/acs.joc.5b00978

  日期：2015.7.17

  It is here demonstrated that the p-bromodienone route, previously reported for calix[4] arenes, is also effective for the functionalization of the calix[6]arene macrocycle. Thus, alcoholic O-nucleophiles can be introduced at the calix[6]arene exo rim. In addition, the reaction of a calix[6]arene p-bromodienone derivative with an actived aromatic substrate, such as resorcinol, led to the first example of a meta-functionalized, inherently chiral calix[6] arene derivative.