5,11,17,23-tetrakis(chlorosulphonyl)calix<4>arene-25,26,27,28-tetraol | 139097-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,11,17,23-tetrakis(chlorosulphonyl)calix<4>arene-25,26,27,28-tetraol
• 英文别名: 5,11,17,23-tetrakis(chlorosulfonyl)calix[4]arene；25,26,27,28-tetrahydroxy-5,11,17,23-tetrakis[cholorosulfonyl]calix[4]arene；25,26,27,28-Tetrahydroxypentacyclo[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-5,11,17,23-tetrasulfonyl chloride
• CAS: 139097-76-0
• 化学式: C₂₈H₂₀Cl₄O₁₂S₄
• 分子量: 818.536
• InChiKey: BJGISZZJVJAEMA-UHFFFAOYSA-N

物化性质

• 沸点：
  946.0±65.0 °C(Predicted)
• 密度：
  1.732±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  48
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  251
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetrakis(chlorosulphonyl)calix<4>arene-25,26,27,28-tetraol 、 若丹明B酰肼 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  杯芳烃和若丹明分子的新型集成传感系统，用于选择性比色和荧光检测活细胞中的Hg2 +离子。

  摘要：

  三个新的和容易的杯芳烃衍生物（5，6和7），将其在杯芳烃骨架的上缘所附四个罗丹明单位，被首先制备并评价在溶液中的金属离子的选择性检测。受体（5）和（7）表示，与其他最具竞争力的金属离子相比，具有超低检测限的荧光输出立即向Hg 2+离子输出，表明它们的高效率和可靠性。对Hg 2+的结合反应还通过发色变化（从无色到浅粉红色）观察到溶液中的离子。此外，还进行了MCF-7或MIA PaCa-2细胞系的体外和生物成像研究，以研究受体在生物系统中的使用，以监测汞离子。结果表明，新受体（5）或（7）具有细胞渗透性，适用于活细胞（MCF-7）或（MIA PaCa-2）中Hg 2+的实时成像，而不会损害健康细胞系（HEK） 293）。

  DOI：

  10.1016/j.saa.2020.118904
• 作为产物：
  描述：

  25,26,27,28-tetrapropyloxycalix[4]arene 在 氯磺酸 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以35%的产率得到5,11,17,23-tetrakis(chlorosulphonyl)calix<4>arene-25,26,27,28-tetraol
  参考文献：
  名称：

  Chlorosulfonylated calix[4]arenes: precursors for neutral anion receptors with a selectivity for hydrogen sulfate

  摘要：

  DOI：

  10.1021/jo00078a052

文献信息

• Covalently anchored chlorosulfonyl-calix[4]arene onto silica gel as an efficient and reusable heterogeneous system for reduction of ketones using NaBH4
  作者：Ashkan Bagheri Chenari、Mandana Saber-Tehrani、Manouchehr Mamaghani、Mohammad Nikpassand

  DOI：10.1007/s10847-019-00894-x

  日期：2019.6.15

  ne-bonded silica gel (CSC[4]A-SG) as a novel heterogeneous catalyst was illustrated by efficient reduction of various ketones to their corresponding alcohols. To illustrate the promoting effect of the catalyst in the reaction, two more series of parallel experiments were also carried out using bare silica gel and no catalyst. The study suggests that this newly synthesized solid catalyst has high binding

  氯磺酰基-杯[4]芳烃键合硅胶（CSC[4]A-SG）作为一种新型多相催化剂的催化活性通过将各种酮有效还原为其相应的醇来说明。为了说明催化剂在反应中的促进作用，还使用裸硅胶和无催化剂进行了另外两个系列的平行实验。该研究表明，这种新合成的固体催化剂通过离子对相互作用对钠阳离子具有高结合趋势，因此可以有效地使用 NaBH4 作为氢供体将酮还原为醇。同样为了证明 CSC[4]A-SG 对钠阳离子的高亲和力和强捕获能力，进行了原子吸收光谱测量。因此，在短时间内观察到酮的定量还原，而催化剂显示出高热稳定性（高达 300°C），并且可以连续回收和重复使用至少五次而不会损失其催化性能。这是首次报道CSC[4]A-SG作为催化剂在化学反应中的应用。
• Evaluation of Anticancer Activities of Novel Facile Synthesized Calix[n]arene Sulfonamide Analogs
  作者：Bahar Yilmaz、Abdullah Tahir Bayrac、Mevlut Bayrakci

  DOI：10.1007/s12010-019-03184-x

  日期：2020.4

  calixarene sulfonamide analogs were synthesized from the reaction of chlorosulfonated calix[n]arene (n: 4, 6, and 8) with N,N'-dimethylethylenediamine or ethylenediamine for the first time and an excellent calixarene sulfonamide analog showing potent and selective cytotoxic activity on some cancer cell lines were discovered. Cytotoxicity of the prepared calix[n]arene sulfonamide analogs towards both cancer

  在这里，新的杯芳烃磺酰胺类似物是由氯磺化杯芳烃[n]芳烃（n：4、6和8）与N，N'-二甲基乙二胺或乙二胺的首次反应合成的，是一种出色的杯芳烃磺酰胺类似物，具有强大的发现了对某些癌细胞系的选择性细胞毒活性。通过进行细胞生长抑制试验评估了制备的杯[n]芳烃磺酰胺类似物对癌细胞和健康细胞系的细胞毒性。在细胞毒性测定结果中，观察到基于磺酰胺类似物的杯[4]芳烃（9）不会影响上皮细胞系（HEK）的生长，并且对抑制某些人类癌细胞系的生长特别有效（ MCF-7和MIA PaCa-2）。
• Application of sulfonamide derivative of calixarene for improvement of mechanical properties and thermal stability of polyurethane composite
  作者：Saeed Taghvaei-Ganjali、Mona Rasouli-Saniabadi、Maryam Sadat Mirmoeini

  DOI：10.1007/s10847-015-0539-2

  日期：2015.10

  A calixarene derivative, 5,11,17,23-tetrakis (hydroxyl ethyl sulfonamide) calix[4]arene, was synthesized through a linear reaction from parent calix[4]arene. This sulfonamide calixarene derivative was used as a precursor to produce calixarene-polyurethane composite. Structural properties of calixarene-based synthesized precursors were studied using spectroscopic techniques such as 1H-NMR, 13C-NMR, and IR. Also, mechanical properties of produced polyurethane composite such as fracture elongation, modulus, and tensile strength were studied which indicated that these properties were deeply dependent upon calixarene ratio in composite. An increase in calixarene ratio resulted in a decrease the fracture elongation. In contrast, an increase in calixarene ratio caused a considerable decrease of modulus and tensile strength. The modulus and tensile strength were increased by 16.98 and 20 % as the calixarene/polyol ratio reached 3 %. Finally, TGA and DSC studies showed that calixarene ratio considerably enhanced the thermal stability of polyurethane.

  通过母体钙[4]炔的线性反应合成了一种钙[4]炔衍生物，即 5,11,17,23-四（羟基乙基磺酰胺）钙[4]炔。这种磺酰胺钙[4]烯衍生物被用作生产钙[4]烯-聚氨酯复合材料的前体。使用 1H-NMR、13C-NMR 和 IR 等光谱技术研究了基于钙基芳香族化合物合成的前体的结构特性。此外，还研究了所制聚氨酯复合材料的机械性能，如断裂伸长率、模量和拉伸强度，结果表明这些性能与复合材料中的钙铝榴烯比例有很大关系。钙基芳香烯比率增加会导致断裂伸长率降低。与此相反，钙基芳香烯比率的增加会导致模量和拉伸强度大幅下降。当卡利沙蕾烯/多元醇比率达到 3% 时，模量和拉伸强度分别增加了 16.98% 和 20%。最后，TGA 和 DSC 研究表明，钙基芳香烯比率大大提高了聚氨酯的热稳定性。
• pK a determination of water-soluble calix[4]arenes
  作者：Seiji Shinkai、Koji Araki、Peter D. J. Grootenhuis、David N. Reinhoudt

  DOI：10.1039/p29910001883

  日期：——

  Neutral, water-soluble 5,11,17,23-tetrakis[bis-(2-hydroxyethyl)aminosulphonyl]calix[4]arene-25,26,27,28-tetraol and 5,11,17,23-tetranitrocalix[4]arene-25,26,27,28-tetraol have been synthesized and the pK(a) values of the OH groups determined in an aqueous system.
• Preparation and Application of Chemically Bonded Silica Supported Calix[4]arene as Reinforced Filler in NR/BR Blend Based Rubber Compounds
  作者：Hediye Mohamadi、Fereshte Motiee、Mandana Saber Tehrani、Saeed Taghvaei-Ganjali

  DOI：10.1134/s1070427219060107

  日期：2019.6

  In this study, we tried to reduce polarization of silica surface by chemically bonding cholorosulfonyl calix[4]arene (CSC[4]A) and silica (Si-O-Cl) to improve dispersion between filler and elastomer. To confirm synthesis of CSC[4]A, H-1 NMR, C-13 NMR, and IR spectrophotometry were used. Obtained composite of chemically bonded silica and CSC[4]A was characterized by TGA. Compounds (contained silica, silica and silane, silica-calix system) were prepared to investigate the effect of silica-calix system (CSC[4]A-SiO2) on the rheological and mechanical properties of rubber compounds based on natural rubber/cis-butadiene rubber (NR/BR) blend in tire tread formulation. The rheological and mechanical properties of three samples were investigated by different devices and a surface morphology was evaluated by FESEM technique. The results revealed that the curing behavior of the compound with CSC[4]A-SiO2 did not significantly differ from other compounds, while reversion was considerably reduced compared with that to other compounds. Also, the mechanical properties of compound with CSC[4]A-SiO2 were improved dramatically especially in fatigue resistance.