5,11,17,23-tetraformyl-25,26,27,28-tetraoctyloxycalix[4]arene | 178232-98-9

• 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-tetraformyl-25,26,27,28-tetraoctyloxycalix[4]arene
• 英文别名: 25,26,27,28-Tetraoctoxypentacyclo[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-tetracarbaldehyde
• CAS: 178232-98-9
• 化学式: C₆₄H₈₈O₈
• 分子量: 985.398
• InChiKey: KUSYRKNCVVZGGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.1
• 重原子数：
  72
• 可旋转键数：
  36
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetraformyl-25,26,27,28-tetraoctyloxycalix[4]arene 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 36.0h， 生成 5,11,17,23-tetra(chloromethyl)-25,26,27,28-tetraoctyloxycalix[4]arene
  参考文献：
  名称：

  Antioxidant phospholipid calix[4]arene mimics as micellular delivery systems

  摘要：

  通过加入 PO3H2 或 NMe3+ 头基，两亲性钙[4]烯被设计成磷脂模拟物。利用 PC12 细胞和三种应激源（H2O2、甲萘醌和谷氨酸），我们建立了安全的钙[4]烯水平，它们不仅能够提供姜黄素的抗氧化载荷，而且还具有固有的抗氧化特性。钙[4]炔似乎是一种有效的合成抗氧化剂，可用作纳米载体进行药物输送。

  DOI：

  10.1039/c3ob41178h
• 作为产物：
  描述：

  1-溴辛烷 在 sodium hydride 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 15.17h， 生成 5,11,17,23-tetraformyl-25,26,27,28-tetraoctyloxycalix[4]arene
  参考文献：
  名称：

  Self-Organized Honeycomb-Patterned Microporous Polystyrene Thin Films Fabricated by Calix[4]arene Derivatives

  摘要：

  Calix[4]arene derivatives bearing carboxyl groups at the upper rim and alkyl groups at the lower rim were synthesized. Micrometer-size porous honeycomb-patterned thin films were prepared by evaporating chloroform solution of polystyrene containing the calixarene derivatives under high humidity. These films were coated on gold electrodes of QCM, and the high-frequency changes were observed to detect volatile organic compounds such as dichlorobenzene.

  DOI：

  10.1021/la100434b

文献信息

• Lower Rim−Upper Rim Hydrogen-Bonded Adducts of Calix[4]arenes
  作者：Remko H. Vreekamp、Willem Verboom、David N. Reinhoudt

  DOI：10.1021/jo9603082

  日期：1996.1.1

  An upper-rim-substituted calix[4]arene tetracarboxylic acid forms hydrogen-bonded duplexes with lower-rim-substituted tetra(4-pyridyl)- and tetra(3-pyridyl)calix[4]arenes in chloroform. The formation of these adducts was studied by extraction experiments. The association constants determined via (1)H NMR dilution experiments in CDCl(3) are 7.6 x 10(3) and 1.3 x 10(3) M(-1) for the 4-pyridyl and the

  上边缘取代的杯[4]芳烃四羧酸与下边缘取代的四（4-吡啶基）-和四（3-吡啶基）杯[4]芳烃在氯仿中形成氢键双键。通过提取实验研究了这些加合物的形成。通过CDCl（3）中的（1）H NMR稀释实验确定的缔合常数分别为4-吡啶基和3-吡啶基衍生物的7.6 x 10（3）和1.3 x 10（3）M（-1）。固态和溶液中的IR研究表明，相互作用是基于氢键，质子转移的程度可以忽略不计。VPO测量值支持1：1加合物的形成。
• Porphyrin Capped with Calix[4]arene Derivative via Hydrogen Bonds
  作者：Satoshi Arai、Haruki Ohkawa、Shinsuke Ishihara、Toshimichi Shibue、Shinji Takeoka、Hiroyuki Nishide

  DOI：10.1246/bcsj.78.2007

  日期：2005.11

  A calix[4]arene–porphyrin duplex was prepared by mixing equimolar amounts of hydroxy or carboxy calix[4]arene derivatives and pyridyl or o-aminophenylporphyrin derivatives. Electrospray ionization mass spectrometry (ESI-MS) was applied to screen a suitable pair of a calix[4]arene and a porphyrin. meso-Tetra(2-pyridyl)porphyrin formed a duplex with tetrahydroxy or tetrahydroxymethylcalix[4]arene via triple or quadruple hydrogen bonds. 1H NMR spectra showed that the tetrahydroxycalix[4]arene was symmetrically located upon the porphyrin ring, whereas trihydroxycalix[4]arene was slanted on the porphyrin ring. The duplex of meso-tetra(2-pyridyl)porphyrinatocobalt(II) and tetrahydroxymethylcalix[4]arene formed a complex with benzylimidazole, which was capable of reversible dioxygen-binding. The capping structure upon porphyrin provided by calix[4]arene raised the life-time of dioxygen-adduct compared with the porphyrin without calix[4]arene.

  通过混合等摩尔量的羟基或羧基钙[4]炔衍生物和吡啶基或邻氨基苯基卟啉衍生物，制备了钙[4]炔-卟啉双联物。介-四（2-吡啶基）卟啉通过三重或四重氢键与四羟基或四羟甲基钙[4]炔形成双链。1H NMR 光谱显示，四羟基钙[4]炔对称地位于卟啉环上，而三羟基钙[4]炔则倾斜地位于卟啉环上。中四(2-吡啶基)卟啉钴(II)和四羟甲基钙[4]炔的双链与苄基咪唑形成复合物，能够可逆地结合二氧。与不含钙[4]炔的卟啉相比，钙[4]炔对卟啉的封盖结构提高了二氧加合物的寿命。
• Porous surfactants from cone conformers of calix[5]arenes
  作者：Petr Dedek、Vaclav Janout、Steven L. Regen

  DOI：10.1021/jo00076a009

  日期：1993.11

  This paper describes the synthesis and monolayer properties of two porous surfactants derived from the calix[5]arene framework that exist as stable cone conformers [i.e., 5,11,17,23,29-pentaformyl-31,32,33,34,35-pentakis(n-octyloxy)calix[5]arene (1a) and an N,N-dimethylthioamide derivative 2a] plus calix[4]arene and calix[6]arene analogs. The introduction of 1a, in and of itself, represents a significant advance in the calixarene area because it provides access to a wide-cavity calixarene that is amenable for further modification at its wider rim.
• Inclusion of Cavitands and Calix[4]arenes into a Metallobridgedpara-(1H-Imidazo[4,5-f][3,8]phenanthrolin-2-yl)-Expanded Calix[4]arene
  作者：Enrique Botana、Eric Da Silva、Jordi Benet-Buchholz、Pablo Ballester、Javier de Mendoza

  DOI：10.1002/anie.200603180

  日期：2007.1