5,11,17,23,29,35-hexa-tert-butyl-37,38,39,40,41-pentamethoxy-42-hydroxycalix<6>arene | 149472-77-5

• 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-37,38,39,40,41-pentamethoxy-42-hydroxycalix<6>arene
• 英文别名: 5,11,17,23,29,35-hexa-tert-butyl-37,38,39,40,41-pentamethoxycalix<6>arene-42-ol；5,11,17,23,29,35-hexa-tert-butyl-38,39,40,41,42-pentamethoxycalix[6]aren-37-ol；5,11,17,23,29,35-hexa-tert-butyl-38,39,40,41,42-pentamethoxycalix<6>aren-37-ol；5,11,17,23,29,35-hexa-tert-butyl-38,39,40,41,42-pentamethoxyethoxycalix<6>aren-37-ol；pentamethoxy-p-tert-butylcalix[6]arenemonool；calix[6]arene-mono-ol；5,11,17,23,29,35-Hexatert-butyl-38,39,40,41,42-pentamethoxyheptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(36),3(42),4,6,9(41),10,12,15,17,19(40),21,23,25(39),27,29,31(38),33(37),34-octadecaen-37-ol
• CAS: 149472-77-5
• 化学式: C₇₁H₉₄O₆
• 分子量: 1043.52
• InChiKey: PPACZKGWOIGKEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.1
• 重原子数：
  77
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 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-37,38,39,40,41-pentamethoxy-42-hydroxycalix<6>arene 在 phenyltrimethylammonium tribromide 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以99%的产率得到
  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：

  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 作用下， 以 乙酸乙酯 为溶剂， 反应 1.5h， 以100%的产率得到5,11,17,23,29,35-hexa-tert-butyl-37,38,39,40,41-pentamethoxy-42-hydroxycalix<6>arene
  参考文献：
  名称：

  De Mendoza; Carramolino; Cuevas, Synthesis, 1994, # 1, p. 47 - 50

  摘要：

  DOI：

文献信息

• Synthesis of calix[6]arenes partially functionalized at the upper rim
  作者：Alessandro Casnati、Laura Domiano、Andrea Pochini、Rocco Ungaro、Mar Carramolino、J. Oriol Magrans、Pedro M. Nieto、Javier López-Prados、Pilar Prados、Javier de Mendoza、Rob G. Janssen、Willem Verboom、David N.Reinhoudt

  DOI：10.1016/0040-4020(95)00826-t

  日期：1995.11

  Several new examples of calix[6]arenes selectively functionalized at the upper rim are reported. Starting from calix[6]arenes 1,3,5-tri-, 1,2,4,5-tetra- and 1,2,3,4,5-pentaalkylated at the lower rim, it is possible to isolate macrocycles 2,4,6-tri-, 3,6-di- and 6-mono functionalized at the upper rim (18–94% yield) with nitro, formyl, bromo, chloromethyl and 2-propenyl groups. Modifications of these

  报告了在上部边缘选择性功能化的杯[6]芳烃的一些新实例。从在下部边缘被烷基化的杯[6]芳烃1,3,5-三-，1,2,4,5-四-和1,2,3,4,5-五烷基开始，有可能分离出大环化合物2 ，4,6-三-，3,6-二-和6-单官能团在上缘被官能化（18-94％的产率），带有硝基，甲酰基，溴，氯甲基和2-丙烯基。这些部分的修饰允许合成带有氨基，酰胺基，羟甲基，羧基，氰基和氯甲基官能团的大环，这些环可以基于杯[6]芳烃（具有不同的几何结构）用于进一步转化和制备新的分子受体。还报道了六聚大环上的二醌和三醌的实例。
• Threading fluorescent calixarene-wheels with ammonium axles
  作者：Carmen Talotta、Tonino Caruso、Margherita De Rosa、Carmine Gaeta、Annunziata Soriente、Placido Neri

  DOI：10.1080/10610278.2018.1424852

  日期：2018.7.3

  synthesis of new calix[6]arene derivatives bearing anthracenyl and naphthyl fluorescent units at the lower rim is here reported. The threading abilities of these new derivatives toward dialkylammonium and bis(benzylalkylammonium) axles were investigated by NMR and fluorescence spectroscopy. A quenching of the fluorescence of the calix-wheels was observed upon threading with ammonium axles. Finally, DFT

  摘要 本文报道了在下缘带有蒽基和萘基荧光单元的新型杯[6]芳烃衍生物的合成。通过核磁共振和荧光光谱研究了这些新衍生物对二烷基铵和双（苄基烷基铵）轴的穿线能力。在用铵轴穿入时观察到杯轮的荧光猝灭。最后，DFT 计算证明，除了轴的铵基和氧原子之间通常的 H 键相互作用之外，在轴和轮的蒽基或萘基之间还存在稳定的 C–H…π 相互作用杯轮。
• Monophosphanylcalix[6]arene Ligands: Synthesis Characterization, Complexation, and Their Use in Catalysis
  作者：Yasushi Obora、Yun Kui Liu、Sho Kubouchi、Makoto Tokunaga、Yasushi Tsuji

  DOI：10.1002/ejic.200500673

  日期：2006.1

  Novel phosphanylcalix[6]arenes having mono-O-diphenylphosphanylmethyl (3) and mono-O-(4-diphenylphosphanylphenyl)methyl substituents (5) have been synthesized. The structures of these monophosphanylcalix[6]arenes were determined by NMR spectroscopy, mass spectrometry, and X-ray crystal structure analysis. The X-ray structure reveals that 3 adopts a flattened 1,2,3-alternate conformation in the crystalline

  已经合成了具有单-O-二苯基膦酰基甲基（3）和单-O-（4-二苯基膦酰基苯基）甲基取代基（5）的新型膦酰基杯[6]芳烃。这些单膦酰基杯[6]芳烃的结构通过核磁共振光谱、质谱和X射线晶体结构分析确定。X 射线结构显示 3 在结晶状态下采用扁平的 1,2,3-交替构象，而核磁共振谱表明 3 和 5 在溶液中具有锥形构象。在 B3LYP/LANL2DZ-CONFLEX5/MMFF94s 理论水平对 3 和 5 的结构优化和能量计算表明，对于 3 和 0.96，锥形构象比 1,2,3-交替构象稍微稳定 0.36 kcal mol-1 kcal mol–1 为 5。3 与 [PtCL2(COD)] 和 [Rh(COD)2]BF4 的络合分别得到顺式配位的 [PtCL2(3)2] 和 [Rh(COD)(3)2]BF4。[PtCL2(3)2] 的 X 射线分析表明 3 在络合时采用锥形构象。3 和 5 与
• Synthesis and Structural Characterization of a Series of Mono-<i>O</i>-(diphenylphosphinobenzyl)calix[6]arenes with and without<i>tert</i>-Butyl Moieties at the Upper Rim
  作者：Tetsuaki Fujihara、Sho Kubouchi、Yasushi Obora、Makoto Tokunaga、Kazuhiro Takenaka、Yasushi Tsuji

  DOI：10.1246/bcsj.82.1187

  日期：2009.9.15

  Synthesis and characterization of a series of mono-O-(diphenylphosphinobenzyl)calix[6]arenes are presented. The two types of calix[6]arene moieties were prepared: 1 (with tert-butyl groups at the upper rim) and 2 (without the tert-butyl groups). With regard to the position of a phosphorus atom, the diphenylphosphino group was introduced onto the ortho, meta, or para positions with the benzyl ether moiety. These phosphines as well as their oxides were fully characterized by elemental analysis, NMR measurements, and HR-ESI-MS. The NMR study indicated that 1 had a cone conformation whereas 2 was very flexible in solution. These phosphines were found to be effective ligands in Rh-catalyzed hydroformylation.

  介绍了一系列单-O-(二苯基膦基苄基)杯[6]芳烃的合成和表征。制备了两种类型的杯[6]芳烃部分：1（上缘有叔丁基）和2（没有叔丁基）。关于磷原子的位置，将二苯基膦基引入到与苄基醚部分的邻位、间位或对位上。这些膦及其氧化物通过元素分析、NMR 测量和 HR-ESI-MS 进行了全面表征。 NMR 研究表明 1 具有锥形构象，而 2 在溶液中非常灵活。这些膦被发现是 Rh 催化的加氢甲酰化反应中的有效配体。
• Procedures for the Selective Alkylation of Calix[6]arenes at the Lower Rim
  作者：Rob G. Janssen、Willem Verboom、David N. Reinhoudt、Alessandro Casnati、Margret Freriks、Andrea Pochini、Franco Ugozzoli、Rocco Ungaro、Pedro M. Nieto、Mar Carramolino、Félix Cuevas、Pilar Prados、Javier de Mendoza

  DOI：10.1055/s-1993-25868

  日期：——

  New partially alkylated calix[6]arenes have been synthesized. Depending on the conditions, mono-, 1,2-di-, 1,3-di, 1,2,3-tri-, 1,3,5-tri-, 1,2,4,5-tetra-, and 1,2,3,4,5-pentamethylated derivatives of p-tert-butylcalix[6]arene could be obtained in moderate to good yields. Methylation or benzylation of the parent calix[6]arene showed a regioselectivity towards 1,2-di-, and 1,2,3-trisubstitution. The solid state structure of 1,2,4,5-tetrasubstituted p-tert-butylcalix[6]arene [R=O(CH2CH2O)2CH3] has been elucidated by X-ray analysis.

  已合成了新的部分烷基化杯[6]芳烃。根据条件不同，可得到单甲基、1,2-二甲基、1,3-二甲基、1,2,3-三甲基、1,3,5-三甲基、1,2,4,5-四甲基和1,2,3,4,5-五甲基对叔丁基杯[6]芳烃衍生物，产率中等至良好。对母体杯[6]芳烃进行甲基化或苄基化后，1,2-二甲基和1,2,3-三甲基取代具有区域选择性。1,2,4,5-四甲基对叔丁基杯[6]芳烃[R=O(CH2CH2O)2CH3]的固态结构已通过X射线分析阐明。