3,25-Dibromo-4,24-bis-bromomethyl-6,22-dimethoxy-8,11,14,17,20-pentaoxa-tricyclo[19.4.0.0^2,7]pentacosa-1(25),2(7),3,5,21,23-hexaene | 917090-38-1

• 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: 3,25-Dibromo-4,24-bis-bromomethyl-6,22-dimethoxy-8,11,14,17,20-pentaoxa-tricyclo[19.4.0.0^2,7]pentacosa-1(25),2(7),3,5,21,23-hexaene
• 英文别名: 3,25-Dibromo-4,24-bis(bromomethyl)-6,22-dimethoxy-8,11,14,17,20-pentaoxatricyclo[19.4.0.02,7]pentacosa-1(25),2,4,6,21,23-hexaene
• CAS: 917090-38-1
• 化学式: C₂₄H₂₈Br₄O₇
• 分子量: 748.098
• InChiKey: BRBGIZXGQSQLQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,25-Dibromo-4,24-bis-bromomethyl-6,22-dimethoxy-8,11,14,17,20-pentaoxa-tricyclo[19.4.0.0^2,7]pentacosa-1(25),2(7),3,5,21,23-hexaene 、 2-(2'-cyanoethylthio)-3,6,7-tris(methylthio)tetrathiafulvalene 在 cesium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以29%的产率得到3,25-Dibromo-6,22-dimethoxy-4,24-bis-(5,4',5'-tris-methylsulfanyl-[2,2']bi[[1,3]dithiolylidene]-4-ylsulfanylmethyl)-8,11,14,17,20-pentaoxa-tricyclo[19.4.0.0^2,7]pentacosa-1(25),2(7),3,5,21,23-hexaene
  参考文献：
  名称：

  基于联苯支架和四硫富瓦烯单元的电活性C 2对称受体

  摘要：

  结合了结合位点的联苯-四硫富瓦烯（TTF）衍生物家族的合成已通过联苯支架的功能化以良好至中等的产率进行。提供了该系列的一个衍生物（化合物3）的X射线结构，该结构显示了以联苯胺单元的中心Ar-Ar键为顺式构象的二面角为74° 。1 H NMR和循环伏安法研究表明，取代的性质对构象刚度和所得联苯-TTF组件的电化学行为至关重要。Pb 2+结合后的原始电化学识别过程突显了此功能与金属阳离子络合时发生的构象变化有关。

  DOI：

  10.1021/jo061446m
• 作为产物：
  描述：

  2-甲氧基-4-甲基苯酚 在 N-溴代丁二酰亚胺(NBS) 、 溴 、 methyltri(butyl)ammonium permanganate 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 3,25-Dibromo-4,24-bis-bromomethyl-6,22-dimethoxy-8,11,14,17,20-pentaoxa-tricyclo[19.4.0.0^2,7]pentacosa-1(25),2(7),3,5,21,23-hexaene
  参考文献：
  名称：

  2,2′-Dihydroxy-3,3′-dimethoxy-5,5′-dimethyl-6,6′-dibromo-1,1′-biphenyl: preparation, resolution, structure and biological activity

  摘要：

  The preparation and resolution of the titled conformationally stable biphenyl 1 has been performed in high chemical yield starting from creosol 2. Enantiopure biphenyls (aR)-(+)-1 and (aS)-(-)-1 were obtained by the corresponding menthylcarbonate diastereomer and successive reduction. The absolute configuration and specific rotation were correlated by X-ray analysis of the crystal structure of diastereopure menthylcarbonate (aS,1R,1'R,2S,2'S,5R,5'R)-(+)-16. Preliminary biological evaluation of both racemic enantiomers of 1 has been carried out on melanoma cell lines and significant and selective anticancer activity has been observed for the enantiomer (aS)-(-)-1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.017

文献信息

• Electroactive <i>C</i>₂ Symmetry Receptors Based on the Biphenyl Scaffold and Tetrathiafulvalene Units
  作者：Giovanna Delogu、Davide Fabbri、Maria Antonietta Dettori、Marc Sallé、Franck Le Derf、Maria-Jesus Blesa、Magali Allain

  DOI：10.1021/jo061446m

  日期：2006.11.1

  moderate yields through functionalization of the biphenyl scaffold. X-ray structure of one derivative (compound 3) of the series is provided and shows a dihedral angle of 74° around the central Ar−Ar bond of the biphenyl unit in a cisoid conformation. 1H NMR and cyclic-voltammetry studies demonstrate the critical importance of the nature of the substitution on the conformational rigidity and on the electrochemical

  结合了结合位点的联苯-四硫富瓦烯（TTF）衍生物家族的合成已通过联苯支架的功能化以良好至中等的产率进行。提供了该系列的一个衍生物（化合物3）的X射线结构，该结构显示了以联苯胺单元的中心Ar-Ar键为顺式构象的二面角为74° 。1 H NMR和循环伏安法研究表明，取代的性质对构象刚度和所得联苯-TTF组件的电化学行为至关重要。Pb 2+结合后的原始电化学识别过程突显了此功能与金属阳离子络合时发生的构象变化有关。
• 2,2′-Dihydroxy-3,3′-dimethoxy-5,5′-dimethyl-6,6′-dibromo-1,1′-biphenyl: preparation, resolution, structure and biological activity
  作者：Davide Fabbri、Maria Antonietta Dettori、Giovanna Delogu、Alessandra Forni、Gianluigi Casalone、Giuseppe Palmieri、Marina Pisano、Carla Rozzo

  DOI：10.1016/j.tetasy.2007.01.017

  日期：2007.2

  The preparation and resolution of the titled conformationally stable biphenyl 1 has been performed in high chemical yield starting from creosol 2. Enantiopure biphenyls (aR)-(+)-1 and (aS)-(-)-1 were obtained by the corresponding menthylcarbonate diastereomer and successive reduction. The absolute configuration and specific rotation were correlated by X-ray analysis of the crystal structure of diastereopure menthylcarbonate (aS,1R,1'R,2S,2'S,5R,5'R)-(+)-16. Preliminary biological evaluation of both racemic enantiomers of 1 has been carried out on melanoma cell lines and significant and selective anticancer activity has been observed for the enantiomer (aS)-(-)-1. (c) 2007 Elsevier Ltd. All rights reserved.