5,11,17,23,29,35-hexa-tert-butyl-37,39,41-trimethoxy-38,40,42-tris(2-tosyloxyethoxy)calix[6]arene | 529019-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,11,17,23,29,35-hexa-tert-butyl-37,39,41-trimethoxy-38,40,42-tris(2-tosyloxyethoxy)calix[6]arene
• 英文别名: 5,11,17,23,29,35-hexa-tert-butyl-37,39,41-trimethoxy-38,40,42-tris(2-tosylethoxy)calix[6]arene；2-[[5,11,17,23,29,35-Hexatert-butyl-38,40,42-trimethoxy-39,41-bis[2-(4-methylphenyl)sulfonyloxyethoxy]-37-heptacyclo[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-octadecaenyl]oxy]ethyl 4-methylbenzenesulfonate
• CAS: 529019-17-8
• 化学式: C₉₆H₁₂₀O₁₅S₃
• 分子量: 1610.2
• InChiKey: APMCUTGOYMUUAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  25.4
• 重原子数：
  114
• 可旋转键数：
  27
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  211
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  tris[2-(N-tosylaminoethyl)]amine 、 5,11,17,23,29,35-hexa-tert-butyl-37,39,41-trimethoxy-38,40,42-tris(2-tosyloxyethoxy)calix[6]arene 在 potassium carbonate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以33%的产率得到
  参考文献：
  名称：

  Ipso-Nitration of Calix[6]azacryptands: Intriguing Effect of the Small Rim Capping Pattern on the Large Rim Substitution Selectivity

  摘要：

  The ipso-nitration of calix[6]arene-based molecular receptors is a important synthetic pathway for the elaboration of more sophisticated systems. This reaction has been studied for a variety of capped calixarenes, and a general trend for the regioselective nitration of three aromatic units out of six in moderate to high yield has been observed. This selectivity is, in part, attributed to the electronic connection between the protonated cap at the small rim and the reactive sites at the large rim. In addition, this work highlights the fact that subtle conformational properties can drastically influence the outcome of this reaction.

  DOI：

  10.1021/jo300179h
• 作为产物：
  描述：

  对甲苯磺酰氯 、 5,11,17,23,29,35-hexa-tert-butyl-37,39,41-trimethoxy-38,40,42-tris(2-hydroxyethoxy)calix[6]arene 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以86%的产率得到5,11,17,23,29,35-hexa-tert-butyl-37,39,41-trimethoxy-38,40,42-tris(2-tosyloxyethoxy)calix[6]arene
  参考文献：
  名称：

  [EN] NEW CALIX ARENE COMPOUNDS, THEIR PROCESS OF PREPARATION AND THEIR USE, PARTICULARLY AS ENZYMATIC MIMES
  [FR] NOUVEAUX COMPOSES DE CALIX ARENES, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION, NOTAMMENT EN TANT QUE MIMES ENZYMATIQUES

  摘要：

  本发明涉及公式(I)的新卡利克斯烷化合物。它还涉及它们的制备过程。本发明还涉及公式(I)化合物与金属、锕系元素、放射性元素、阳离子客体或阴离子客体之间的络合物。本发明还涉及一种包含公式(I)化合物与药用载体结合的药物组合物。本发明还涉及一种制备水溶性化合物的方法，包括硝化或磺化或硝化的反应，特别是公式(I)化合物的反应，以及所得到的化合物。

  公开号：

  WO2004085441A1

文献信息

• [EN] NEW CALIX ARENE COMPOUNDS, THEIR PROCESS OF PREPARATION AND THEIR USE, PARTICULARLY AS ENZYMATIC MIMES<br/>[FR] NOUVEAUX COMPOSES DE CALIX ARENES, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION, NOTAMMENT EN TANT QUE MIMES ENZYMATIQUES
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2004085441A1

  公开（公告）日：2004-10-07

  The present invention relates to new calix arene compounds of formula (I). It also relates to their process of preparation. The present invention also relates to complexes between a compound of formula (I) and an element chosen among a metal, an actinide, a radioelement, a cationic guest or an anionic guest. The present invention also relates to a pharmaceutical composition comprising a compound of formula (I) in association with a pharmaceutically acceptable carrier. The present invention also relates to a process of preparation of water-soluble compounds, comprising a reaction of nitration or sulfonation or nitration, particularly of compounds of formula (I), and also to the compounds such as obtained.

  本发明涉及公式(I)的新卡利克斯烷化合物。它还涉及它们的制备过程。本发明还涉及公式(I)化合物与金属、锕系元素、放射性元素、阳离子客体或阴离子客体之间的络合物。本发明还涉及一种包含公式(I)化合物与药用载体结合的药物组合物。本发明还涉及一种制备水溶性化合物的方法，包括硝化或磺化或硝化的反应，特别是公式(I)化合物的反应，以及所得到的化合物。
• Synthesis and Conformational Study of the First Triply Bridged Calix[6]azatubes
  作者：Stéphane Le Gac、Xianshun Zeng、Olivia Reinaud、Ivan Jabin

  DOI：10.1021/jo048137l

  日期：2005.2.1

  The first C3v- and D3h-symmetrical triply bridged calix[6]azatubes were prepared in good yields from the known 1,3,5-tris-methylated calix[6]arene through an efficient [1 + 1] macrocyclization reaction. A remarkably regioselective hexa ipso-nitration reaction led to a calix[6]azatube substituted at the wide rim in alternate position by tBu and nitro groups. A 1H NMR study showed that, whereas the parent

  通过有效的[1 + 1]大环化，从已知的1,3,5-三甲基化杯[6]芳烃中以高收率制备了首批C 3 v-和D 3 h对称三重桥连杯[6]氮杂管。反应。显着区域选择性六本位-nitration反应导致了杯[6] azatube在由交替位置的宽边沿取代吨Bu和硝基。A 11 H NMR研究表明，虽然母体双杯[6]芳烃自包含其甲氧基，从而封闭了它们的内管，但硝基取代的杯[6]氮杂管却随着甲氧基的排出而发生构象变化，因此，提出了一种针对主机应用程序开放的三维结构。
• First enantiopure calix[6]aza-cryptand: synthesis and chiral recognition properties towards neutral molecules
  作者：Eva Garrier、Stéphane Le Gac、Ivan Jabin

  DOI：10.1016/j.tetasy.2005.10.039

  日期：2005.11

  The synthesis of the first enantiopure calix[6]aza-cryptand was achieved in five steps from the known 1,3,5-tris-O-methylated calix[6]arene. A 1H NMR spectroscopic study has shown that the chiral tren cap constrains the calixarene core in a straight cone conformation ideal for host–guest chemistry applications. As a result, the tetra-protonated derivative displays remarkable host properties towards

  从已知的1,3,5-tris-O-甲基化的杯[6]芳烃中分五个步骤完成了第一对映体纯杯[6] aza-cryptand的合成。阿1 1 H NMR光谱研究已经表明，手性TREN帽约束在一条直线锥形构象的理想主客体化学应用的杯芳烃芯。结果，四质子化的衍生物对极性中性分子显示出显着的宿主特性，并且手性客体已经证明了对映选择性识别过程。
• <i>Ipso</i>-Nitration of Calix[6]azacryptands: Intriguing Effect of the Small Rim Capping Pattern on the Large Rim Substitution Selectivity
  作者：Manuel Lejeune、Jean-François Picron、Alice Mattiuzzi、Angélique Lascaux、Stéphane De Cesco、Andrea Brugnara、Gregory Thiabaud、Ulrich Darbost、David Coquière、Benoit Colasson、Olivia Reinaud、Ivan Jabin

  DOI：10.1021/jo300179h

  日期：2012.4.20

  The ipso-nitration of calix[6]arene-based molecular receptors is a important synthetic pathway for the elaboration of more sophisticated systems. This reaction has been studied for a variety of capped calixarenes, and a general trend for the regioselective nitration of three aromatic units out of six in moderate to high yield has been observed. This selectivity is, in part, attributed to the electronic connection between the protonated cap at the small rim and the reactive sites at the large rim. In addition, this work highlights the fact that subtle conformational properties can drastically influence the outcome of this reaction.
• First <i>C</i>₃<i>_v</i>-Symmetrical Calix[6](aza)crown
  作者：Ivan Jabin、Olivia Reinaud

  DOI：10.1021/jo026642h

  日期：2003.5.1

  The first C-3nu-symmetrical calix[6](aza)crown 8 has been obtained in five steps from X6H3Me3 3. The key-step introduction of the triple bridge at the small rim has been achieved through reaction of a tris-arylsulfonamide derivative of tren 1 and tris-tosylcalix[6]arene 6. A H-1 NMR study has shown that the tripodal cap rigidifies the whole edifice, preventing ring inversion and constraining the calixarene core in a straight cone conformation.