3,3'-(1,3-phenylenebis(methylene-oxy))dibenzaldehyde | 441799-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,3'-(1,3-phenylenebis(methylene-oxy))dibenzaldehyde
• 英文别名: 3-[[3-[(3-Formylphenoxy)methyl]phenyl]methoxy]benzaldehyde；3-[[3-[(3-formylphenoxy)methyl]phenyl]methoxy]benzaldehyde
• CAS: 441799-13-9
• 化学式: C₂₂H₁₈O₄
• 分子量: 346.383
• InChiKey: XMSNECNUMJPPRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3'-(1,3-phenylenebis(methylene-oxy))dibenzaldehyde 在 chromium(VI) oxide 、 硫酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 2.0h， 生成 1-{3-[3-(3-Propynoyl-phenoxymethyl)-benzyloxy]-phenyl}-propynone
  参考文献：
  名称：

  An Enaminone-Directed Benzannulation/Macrocyclization Approach to Cyclophane Ring Systems

  摘要：

  A straightforward and modular preparative approach to 1,3,5-triaroylbenzene-based functionalized cyclophane ring systems has been developed. The key cyclophane-forming macrocyclization reaction was accomplished during the course of a regioselective cross-benzannulation between bis(aryl ethynyl) ketone and enaminone reactants. Macrocyclic products with ring sizes ranging from 18-to 22-membered were successfully constructed. The composition of the tether connecting the two aryl ethynyl ketone fragments can be easily varied; consequently, this method is suitable for construction of a diverse range of structurally distinct cyclophane products. To illustrate this feature, cyclophanes possessing xylyl, alkyl, di(ethylene triamine), and di(ethylene oxy) bridging units were synthesized in isolated yields of 11-46%. Three new cyclophanes (calixarene-like macrocyles 8 and 9, as well as crownophane 18) were structurally characterized by X-ray diffractometry.

  DOI：

  10.1021/jo0256181
• 作为产物：
  描述：

  间羟基苯甲醛 、 间二溴苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以91%的产率得到3,3'-(1,3-phenylenebis(methylene-oxy))dibenzaldehyde
  参考文献：
  名称：

  Synthesis, Antimicrobial Activity, and Molecular Docking Study of Some Novel Cyclophanes with Imino Intra-Annular Functionality

  摘要：

  本文介绍了含有各种间隔单元的新型亚氨基环烷的合成和结构特征。所有亚氨基环烷对革兰氏阳性（枯草芽孢杆菌、金黄色葡萄球菌）和革兰氏阴性（大肠埃希氏菌、肺炎克雷伯氏菌）细菌菌株都具有相当的抗菌活性。亚氨基环烷还对人类致病真菌白色念珠菌表现出良好的抗真菌活性。

  DOI：

  10.1071/ch12326

文献信息

• Synthesis of linked 1,3,5-triaroylbenzenes via enamine-directed alkyne cyclotrimerization
  作者：F.Christopher Pigge、Fatemeh Ghasedi

  DOI：10.1016/s0040-4039(00)01125-4

  日期：2000.8

  Triaroylbenzenes connected via m-xylyl, p-xylyl, 4,4'-biphenyl, and 1,3,5-benzenetriyl linking units have been prepared in good yield by condensation of bis(enaminones) with aryl ethynyl ketones, The required bis(enaminones) were conveniently prepared starting from the corresponding bis- or tris(halomethyl) linking units and 3-hydroxybenzaldehyde. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Bis(oxyphenylene)benzimidazoles: A novel class of anti-Plasmodium falciparum agents
  作者：Annie Mayence、Jean Jacques Vanden Eynde、Marcel Kaiser、Reto Brun、Nigel Yarlett、Tien L. Huang

  DOI：10.1016/j.bmc.2011.10.039

  日期：2011.12

  A small library of 26 2,2'-[alkane-alpha,omega-diylbis(oxyphenylene)] bis-1H-benzimidazoles has been prepared and evaluated against Giardia intestinalis, Entamoeba histolytica, Trypanosoma brucei rhodesiense, Trypanosoma cruzi, Leishmania donovani, and Plasmodium falciparum. Among the tested compounds, eight derivatives (17, 19, 20, 24, 27, 30, 32 and 35) exhibited an anti-Plasmodium falciparum activity characterized by IC50 values in the range of 180-410 nM (0.11-0.21 mu g/mL) and selectivity indexes (IC50 rat skeletal myoblasts L6 cells vs IC50 P. falciparum K1 strain) varying between 92 and more than 450. Two of the eight novel drug leads, namely compounds 19 and 32, were also active against G. intestinalis and L. donovani with selectivity indexes of 122 and > 164 respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• An Enaminone-Directed Benzannulation/Macrocyclization Approach to Cyclophane Ring Systems
  作者：F. Christopher Pigge、Fatemeh Ghasedi、Nigam P. Rath

  DOI：10.1021/jo0256181

  日期：2002.6.1

  A straightforward and modular preparative approach to 1,3,5-triaroylbenzene-based functionalized cyclophane ring systems has been developed. The key cyclophane-forming macrocyclization reaction was accomplished during the course of a regioselective cross-benzannulation between bis(aryl ethynyl) ketone and enaminone reactants. Macrocyclic products with ring sizes ranging from 18-to 22-membered were successfully constructed. The composition of the tether connecting the two aryl ethynyl ketone fragments can be easily varied; consequently, this method is suitable for construction of a diverse range of structurally distinct cyclophane products. To illustrate this feature, cyclophanes possessing xylyl, alkyl, di(ethylene triamine), and di(ethylene oxy) bridging units were synthesized in isolated yields of 11-46%. Three new cyclophanes (calixarene-like macrocyles 8 and 9, as well as crownophane 18) were structurally characterized by X-ray diffractometry.
• Synthesis, Antimicrobial Activity, and Molecular Docking Study of Some Novel Cyclophanes with Imino Intra-Annular Functionality
  作者：Perumal Rajakumar、Ramar Padmanabhan、Chandrasekaran Ramprasath、Narayanasamy Mathivanan、Vaidhyanathan Silambarasan、Devadasan Velmurugan

  DOI：10.1071/ch12326

  日期：——

  The synthesis and structural characterisation of novel imino cyclophanes incorporating various spacer units is described. All the imino cyclophanes exhibit comparable antibacterial activity against Gram positive (Bacillus subtillus, Staphylococcus aureus) and Gram negative (Escherchia coli, Klebsiella pneumonia) bacterial strains. The imino cyclophanes also exhibit good antifungal activity against human pathogenic fungus, Candida albicans.

  本文介绍了含有各种间隔单元的新型亚氨基环烷的合成和结构特征。所有亚氨基环烷对革兰氏阳性（枯草芽孢杆菌、金黄色葡萄球菌）和革兰氏阴性（大肠埃希氏菌、肺炎克雷伯氏菌）细菌菌株都具有相当的抗菌活性。亚氨基环烷还对人类致病真菌白色念珠菌表现出良好的抗真菌活性。