11,17,23-Tritert-butyl-25,26,27-tripropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,6,9,11,13(27),15(26),16,18,21(25),22-undecaene-5,28-dione | 518981-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 11,17,23-Tritert-butyl-25,26,27-tripropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,6,9,11,13(27),15(26),16,18,21(25),22-undecaene-5,28-dione
• 英文别名: 11,17,23-tritert-butyl-25,26,27-tripropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,6,9,11,13(27),15(26),16,18,21(25),22-undecaene-5,28-dione
• CAS: 518981-39-0
• 化学式: C₄₉H₆₄O₅
• 分子量: 733.044
• InChiKey: BCQGZDHEHOSXLL-UHFFFAOYSA-N

物化性质

• 沸点：
  789.5±60.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  54
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  11,17,23-Tritert-butyl-25,26,27-tripropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,6,9,11,13(27),15(26),16,18,21(25),22-undecaene-5,28-dione 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 以49%的产率得到11,17,23-Tritert-butyl-25,26,27-tripropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-5,28-diol
  参考文献：
  名称：

  Nitric Oxide Release Mediated by Calix[4]hydroquinones

  摘要：

  Calix[4]monohydroquinone has been used as a supramolecular system for the generation of NO gas. In a one-electron reduction scheme involving NO+subset of calix[4]monohydroquinone complex, NO is released without the presence of an external reducing agent. Free calix[4]monoquinone, thus obtained, can be reused for a new NO-releasing cycle after NaBH4-reduction to calix[4]monohydroquinone.

  DOI：

  10.1021/ol800156m
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 在 thallium(III) trifluoroacetate 作用下， 以 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 12.0h， 生成 11,17,23-Tritert-butyl-25,26,27-tripropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,6,9,11,13(27),15(26),16,18,21(25),22-undecaene-5,28-dione
  参考文献：
  名称：

  Synthesis and self-assembly of novel calix[4]arenocrowns: formation of calix[4]areno[2]catenanes

  摘要：

  A series of novel calix[4]arenocrowns la-c were efficiently synthesized by a one-pot reaction of calix[4]monohydroquinone diacetate 5 with ditosylate 6 and its analogues in the presence of sodium hydroxide. It was found that the calix[4]arenocrowns could form stable pseudorotaxane-type complexes 2a-c with paraquat, and further self-assemble into calix[4]areno[2]catenanes 3a-C with dicationic salt 8 and p-bis(bromomethyl)benzene. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.108

文献信息

• The <i>p</i>-Bromodienone Route to Nucleophilic Functionalization of Calixarene <i>Exo</i> Rim
  作者：Francesco Troisi、Teresa Pierro、Carmine Gaeta、Placido Neri

  DOI：10.1021/ol8027708

  日期：2009.2.5

  Easily accessible calixarene p-bromodienone derivatives undergo a silver-mediated nucleophilic substitution and a subsequent rearomatization with a range of different O-nucleophiles (alcohols and carboxylates) to give p-alkoxy- or p-acyloxycalixarenes in workable yields. This approach can be considered a general “p-bromodienone route” to functionalize calixarene exo rim with nucleophiles.

  容易获得的杯芳烃对-溴代双烯酮衍生物经过银介导的亲核取代，随后用一系列不同的O-亲核体（醇和羧酸酯）进行重新麦芽糖化，以可行的产率得到对-烷氧基-或对-酰氧基杯芳烃。这种方法可以被认为是一般的“ p -bromodienone路线”功能化杯芳烃外与亲核边缘。
• Oxyfunctionalization of Calixarene Quinone Rings
  作者：Francesco Troisi、Lucia Citro、Carmine Gaeta、Enrico Gavuzzo、Placido Neri

  DOI：10.1021/ol800090u

  日期：2008.4.1

  The epoxidation of quinone rings of calixquinones represents a valid route for the introduction of oxygenated functionalities into the de-tert-butylated calixarene walls originating cis-diepoxy-p-dione moieties. Carbonyl reduction of these systems leads to hybrid calixarenes containing dianhydroinositol moieties (calixinositols) belonging to the calixcyclitols family. The regio- and stereochemistry

  杯醌醌的醌环的环氧化代表了将氧化官能团引入源自顺式-二环氧-对二酮基团的叔丁基化杯芳烃壁的有效途径。这些系统的羰基还原导致杂化杯芳烃，其含有属于杯糖醇类家族的双脱水肌醇部分（杯芯糖醇）。这些衍生物的区域和立体化学是通过2D NMR研究以及MM3计算和X射线晶体学确定的。
• Electrochemistry and ion-sensing properties of calix[4]arene derivatives
  作者：Shanshan Chen、Richard D. Webster、Carmen Talotta、Francesco Troisi、Carmine Gaeta、Placido Neri

  DOI：10.1016/j.electacta.2010.06.076

  日期：2010.9

  The cyclic voltammetric properties of several substituted calix[4]arenes were examined in acetonitrile and dichloromethane. The compounds that contained one phenolic group in the macrocyclic cavity were able to be electrochemically oxidised at positive potentials. In acetonitrile, cyclic voltammetry experiments indicated that the phenolic compounds were oxidised in a two-electron (one-proton) process over all measured scan rates (up to 50 Vs(-1)), while in dichloromethane, the oxidation process occurred by one-electron at scan rates >= 5 V s(-1), to most likely form the radical cations. In both solvents, longer timescale (minutes to hours) controlled potential coulometry experiments indicated that the oxidation process occurred by two-electrons per molecule, to form reactive diamagnetic cations that could not be reduced back to the starting materials under electrolysis conditions. The ion-sensing properties of the compounds were investigated in polymer membrane ion-selective electrodes and it was found that they responded reversibly in a Nernstian fashion to Groups 1 and 2 metals and had the highest selectivity to the cesium cation. (C) 2010 Elsevier Ltd. All rights reserved.
• Nitric Oxide Release Mediated by Calix[4]hydroquinones
  作者：Eranda Wanigasekara、Carmine Gaeta、Placido Neri、Dmitry M. Rudkevich

  DOI：10.1021/ol800156m

  日期：2008.3.1

  Calix[4]monohydroquinone has been used as a supramolecular system for the generation of NO gas. In a one-electron reduction scheme involving NO+subset of calix[4]monohydroquinone complex, NO is released without the presence of an external reducing agent. Free calix[4]monoquinone, thus obtained, can be reused for a new NO-releasing cycle after NaBH4-reduction to calix[4]monohydroquinone.
• Synthesis and self-assembly of novel calix[4]arenocrowns: formation of calix[4]areno[2]catenanes
  作者：Lin-Gang Lu、Guang-Ke Li、Xiao-Xia Peng、Chuan-Feng Chen、Zhi-Tang Huang

  DOI：10.1016/j.tetlet.2006.06.108

  日期：2006.8

  A series of novel calix[4]arenocrowns la-c were efficiently synthesized by a one-pot reaction of calix[4]monohydroquinone diacetate 5 with ditosylate 6 and its analogues in the presence of sodium hydroxide. It was found that the calix[4]arenocrowns could form stable pseudorotaxane-type complexes 2a-c with paraquat, and further self-assemble into calix[4]areno[2]catenanes 3a-C with dicationic salt 8 and p-bis(bromomethyl)benzene. (c) 2006 Elsevier Ltd. All rights reserved.