49,50,51,52,53,54,55,56-Octaethoxycarbonylmethyleneoxycalix[8]arene | 97600-47-0

• 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: 49,50,51,52,53,54,55,56-Octaethoxycarbonylmethyleneoxycalix[8]arene
• 英文别名: octaethyl calix[8]areneoctaacetate；49,50,51,52,53,54,55,56-octakis(ethoxycarbonylmethoxy)calix[8]arene；Ethyl 2-[[50,51,52,53,54,55,56-heptakis(2-ethoxy-2-oxoethoxy)-49-nonacyclo[43.3.1.13,7.19,13.115,19.121,25.127,31.133,37.139,43]hexapentaconta-1(49),3(56),4,6,9(55),10,12,15(54),16,18,21(53),22,24,27,29,31(52),33,35,37(51),39,41,43(50),45,47-tetracosaenyl]oxy]acetate
• CAS: 97600-47-0
• 化学式: C₈₈H₉₆O₂₄
• 分子量: 1537.72
• InChiKey: QCZGDJBZLUEUQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.4
• 重原子数：
  112
• 可旋转键数：
  40
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  284
• 氢给体数：
  0
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  49,50,51,52,53,54,55,56-Octaethoxycarbonylmethyleneoxycalix[8]arene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 49,50,51,52,53,54,55,56-Octakis(2-hydroxyethoxy)calix<8>arene
  参考文献：
  名称：

  Synthesis and Structural Characterization of Calix[4]arenes, Calix[6]arenes, and Calix[8]arenes with 3-Hydroxypropoxy or 2-Hydroxyethoxy Functional Groups Appended onto the Lower Rim

  摘要：

  The compound 5,11,17,23,29,35-hexa-tert-butyl-37,39,41-trihydroxy-38,40,42-trimethoxycalix[6]arene, 1, has been prepared by treating 5,11,17,23,29,35-hexa-tert-butylcalix[6]arene with potassium carbonate, followed by methyl p-toluenesulfonate. The analogous reaction with the unsubstituted calix[6]arene gives 37,38,39-trihydroxy-40,41,42-trimethoxycalix[6]arene 2. Treating 1 or 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-dimethoxycalix[4]arene 3, with sodium hydride followed by allyl bromide gives 5,11,17,23,29,35-hexa-tert-butyl-37,39,41-tris(allyloxy)-38,40,42-trimethoxycalix[6]arene, 4, or 5,11,17,23-tetra-tert-butyl-25,27-bis(allyloxy)-26,28-dimethoxycalix[4]arene, 5, respectively. Compounds 4 and 5 react with BH3, followed by H2O2 to give 5,11,17,23,29,35-hexa-tert-butyl-37,39,41-tris(3-hydroxypropoxy)-38,40,42-trimethoxycalix[6] arene, 6, and 5,11,17,23-tetra-tert-butyl-25,27-bis(3-hydroxypropoxy)-26,28-dimethoxycalix[4]arene, 7, respectively. A general procedure for the synthesis of 2-hydroxyethoxy-substituted calixarenes involves reduction of the corresponding ethyl calixaryl acetates with LiAlH4. The procedure has been used to synthesize 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(2-hydroxyethoxy)calixarene, 8, 25,26,27,28-tetra(2-hydroxyethoxy)calix[4]arene, 9, 5,11,17,23,29,35-hexa-tert-butyl-37,38,39,40,4142-hexakis(2-hydroxyethoxy)calix[6]arene 10, 37,38,39,40,41,42-hexa(2-hydroxyethoxy)calix[6]arene, 11, 5,11,17,23,29,35,41,47-octa-tert-butyl-49,50,51,52,53,54,55,56-octakis(2-hydroxyethoxy)calix[8]arene, 12, and 49,50,51,52,53,54,55,56-octakis(2-hydroxyethoxy)calix[8]arene, 13. Compounds 2, 4, 5, 9, and 10 have been characterized by X-ray crystallography. The conformations of the tetrols, hexols, and octols have been computationally explored using molecular mechanics calculations.

  DOI：

  10.1021/jo00099a032
• 作为产物：
  描述：

  冠-8-烯 、 氯乙酸乙酯 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 生成 49,50,51,52,53,54,55,56-Octaethoxycarbonylmethyleneoxycalix[8]arene
  参考文献：
  名称：

  杯[n]芳烃多羟基胺衍生物的合成，X射线晶体结构和抗肿瘤活性

  摘要：

  基于杯芳烃的化合物是抗癌的高效治疗剂。这项研究旨在制备一系列杯芳烃[n] arene（n = 4，6，8）多羟基胺衍生物（3a–3m），并研究其潜在的抗肿瘤活性。通过X射线衍射确定杯[4]芳烃衍生物3a的单晶结构。我们通过进行癌细胞生长抑制试验评估了制备的杯[n]芳烃多羟基胺衍生物在六种癌细胞系中诱导细胞毒性的能力。结果表明，化合物3a–3d的IC 50值范围为1.6μM至11.3μM。在不同的化合物中，3a和3b在抑制SKOV3细胞生长方面发挥了最强的细胞毒性作用。关于细胞毒性作用的潜在机制，细胞周期分析显示，SKOV3细胞暴露于3a诱导的细胞周期停滞在G0 / G1期，表明DNA合成减少。免疫荧光染色表明，细胞中caspase-3和p53的蛋白表达水平显着增加，而Bcl-2的蛋白表达被有效抑制。同时，在SKOV3细胞中未观察到Bax的显着变化。这些结果表明，可以将杯芳烃3a作为潜在的抗癌剂进行进一步研究。

  DOI：

  10.1016/j.ejmech.2016.07.016

文献信息

• Synthesis, x-ray crystal structures, and cation-binding properties of alkyl calixaryl esters and ketones, a new family of macrocyclic molecular receptors
  作者：Francoise Arnaud-Neu、Elizabeth M. Collins、Mary Deasy、George Ferguson、Stephen J. Harris、Branko Kaitner、Alan J. Lough、M. Anthony McKervey、Elizabeth Marques

  DOI：10.1021/ja00205a018

  日期：1989.11

  Des calix[n]arenes (n=4, 6, 8) portant des cetoesters sont etudies; pour n=4, ils presentent a l'etat solide une conformation en cone, leurs cryptates avec des metaux alcalins sont egalement etudies dans le but d'evaluer leurs proprietes ionophores

  Des calix[n]arenes (n=4, 6, 8) 重要的 des cetoesters 研究；Pour n=4, ils presentent a l'etat solide une conconation en conconation, leurs cryptates avec des metaux alcalins sont egalement etudies dans le but d'evaluer leurs proprietes ionophores
• Synthesis, X-ray crystal structures, and cation transfer properties of alkyl calixaryl acetates, a new series of molecular receptors
  作者：M. Anthony McKervey、Eileen M. Seward、George Ferguson、Barbara Ruhl、Stephen J. Harris

  DOI：10.1039/c39850000388

  日期：——

  Calix[4]-, [6]-, and [8]-arenes have been converted into a series of alkyl acetates which show significant phase-transfer activity and selectivity towards alkali metal picrates; the X-ray crystal structure of two members of the series, (1b) and (2d), have been determined.

  杯[4]-，[6]-和[8]-芳烃已被转化为一系列的乙酸烷基酯，它们显示出显着的相转移活性和对碱金属苦味酸盐的选择性。已经确定了两个系列（1b）和（2d）的X射线晶体结构。
• Synthesis of Functional Aromatic Multisulfonyl Chlorides and Their Masked Precursors
  作者：Virgil Percec、Tushar K. Bera、Binod B. De、Yasuyuki Sanai、Jason Smith、Marian N. Holerca、Bogdan Barboiu、Robert B. Grubbs、Jean M. J. Fréchet

  DOI：10.1021/jo001694x

  日期：2001.3.1

  yl)phenoxyacetyl]oxy]methyl]-1,3-propanediyl ester (27), 5,11,17,23-tetrakis(chlorosulfonyl)-25,26,27,28-tetrakis(ethoxycarbonylmethoxy)calix[4]arene (38), 5,11,17,23,29,35-hexakis(chlorosulfonyl)-37,38,39,40,41,42-hexakis(ethoxycarbonylmethoxy)calix[6]arene (39), 5,11,17,23,29,35,41,47-octakis(chlorosulfonyl)-49,50,51,52,53,54,55,56-octakis(ethoxycarbonylmethoxy)calix[8]arene (40), 5,11,17,23-tet

  含有苯乙酮和两个磺酰氯基团的功能性芳族双（磺酰氯）的合成，即3,5-双[4-（氯磺酰基）苯基] -1-乙酰苯（16），3,5-双（氯磺酰基） -1-苯乙酮（17）和3,5-双（4-（氯磺酰基）苯氧基）-1-苯乙酮（18）通过一系列反应进行，最后一步涉及S-（芳基）的定量氧化氯化-描述了N，N′-二乙基硫代氨基甲酸酯，烷基-或苄基硫代苯基作为磺酰氯的掩蔽的非反应性前体。相关的反应顺序用于合成芳族三磺酰氯1,1,1-三（4-氯磺酰苯基）乙烷（24）。4-（氯磺酰基）苯氧基乙酸，2,2-双[[[[（4-（氯磺酰基）苯氧基乙酰基]氧基]甲基] -1,3-丙二酸酯（27），5,11,17,23-四（氯磺酰基） -25,26,27，28-四（乙氧羰基甲氧基）杯[4]芳烃（38），5,11,17,23,29,35-六（氯磺酰基）-37,38,39,40,41,42-六（乙氧羰基甲氧基）杯[ 6]芳烃（39），5
• Synthesis and Structural Characterization of Calix[4]arenes, Calix[6]arenes, and Calix[8]arenes with 3-Hydroxypropoxy or 2-Hydroxyethoxy Functional Groups Appended onto the Lower Rim
  作者：Justin K. Moran、Emil M. Georgiev、Alex T. Yordanov、Joel T. Mague、D. Max Roundhill

  DOI：10.1021/jo00099a032

  日期：1994.10

  The compound 5,11,17,23,29,35-hexa-tert-butyl-37,39,41-trihydroxy-38,40,42-trimethoxycalix[6]arene, 1, has been prepared by treating 5,11,17,23,29,35-hexa-tert-butylcalix[6]arene with potassium carbonate, followed by methyl p-toluenesulfonate. The analogous reaction with the unsubstituted calix[6]arene gives 37,38,39-trihydroxy-40,41,42-trimethoxycalix[6]arene 2. Treating 1 or 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-dimethoxycalix[4]arene 3, with sodium hydride followed by allyl bromide gives 5,11,17,23,29,35-hexa-tert-butyl-37,39,41-tris(allyloxy)-38,40,42-trimethoxycalix[6]arene, 4, or 5,11,17,23-tetra-tert-butyl-25,27-bis(allyloxy)-26,28-dimethoxycalix[4]arene, 5, respectively. Compounds 4 and 5 react with BH3, followed by H2O2 to give 5,11,17,23,29,35-hexa-tert-butyl-37,39,41-tris(3-hydroxypropoxy)-38,40,42-trimethoxycalix[6] arene, 6, and 5,11,17,23-tetra-tert-butyl-25,27-bis(3-hydroxypropoxy)-26,28-dimethoxycalix[4]arene, 7, respectively. A general procedure for the synthesis of 2-hydroxyethoxy-substituted calixarenes involves reduction of the corresponding ethyl calixaryl acetates with LiAlH4. The procedure has been used to synthesize 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(2-hydroxyethoxy)calixarene, 8, 25,26,27,28-tetra(2-hydroxyethoxy)calix[4]arene, 9, 5,11,17,23,29,35-hexa-tert-butyl-37,38,39,40,4142-hexakis(2-hydroxyethoxy)calix[6]arene 10, 37,38,39,40,41,42-hexa(2-hydroxyethoxy)calix[6]arene, 11, 5,11,17,23,29,35,41,47-octa-tert-butyl-49,50,51,52,53,54,55,56-octakis(2-hydroxyethoxy)calix[8]arene, 12, and 49,50,51,52,53,54,55,56-octakis(2-hydroxyethoxy)calix[8]arene, 13. Compounds 2, 4, 5, 9, and 10 have been characterized by X-ray crystallography. The conformations of the tetrols, hexols, and octols have been computationally explored using molecular mechanics calculations.
• Moran Justin K., Georgiev Emil M., Yordanov Alex T., Mague Joel T., Round+, J. Org. Chem, 59 (1994) N 20, S 5990-5998
  作者：Moran Justin K., Georgiev Emil M., Yordanov Alex T., Mague Joel T., Round+

  DOI：——

  日期：——