1,10-bis(3-formylphenoxy)decane | 115291-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,10-bis(3-formylphenoxy)decane
• 英文别名: 3,3'-[decane-1,10-diylbis(oxy)]dibenzaldehyde；Decamethylendioxy-3,3'-dibenzaldehyd；3-[10-(3-Formylphenoxy)decoxy]benzaldehyde
• CAS: 115291-37-7
• 化学式: C₂₄H₃₀O₄
• 分子量: 382.5
• InChiKey: WKGQYRYFJSRYCO-UHFFFAOYSA-N

物化性质

• 沸点：
  539.1±25.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  1,10-bis(3-formylphenoxy)decane 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 14.0h， 生成 N,N'-(5,5'-(3,3'-(decane-1,10-diylbis(oxy))bis(3,1-phenylene))bis(4-acetyl-4,5-dihydro-1,3,4-thiadiazole-5,2-diyl))diacetamide
  参考文献：
  名称：

  New 1,3,4-bisthiadiazolines: Synthesis, characterization and antimicrobial evaluations

  摘要：

  The bisthiadiazolines 4a-4g have been synthesized in good yields from the cyclization reactions of bisthiosemicarbazones 3a-3g with acetic anhydride. The condensation reaction of dibenzaldehydes 2a-2g with thiosemicarbazide in alcoholic medium provided 3a-3g and former were obtained from the O-alkylation of 3-hydroxybenzaldehyde with suitable 1,omega-dibromoalkanes under alkaline conditions in the presence of dry EtOH/DMF. The intermediates 3a-3g and bishetrocyclics 4a-4g were also screened for their in vitro antimicrobial activities against seven bacterial strains (Klubsellia pneumoniae, Pseudomonas aeruginosa, Escherichia coli, Straphylococcus aureus, Bacillius subtilis, Pseudomonas fluorescens and Streptoccus pyrogens) and five fungi strains (Aspergillius Janus, Pencillium glabrum, Fusarium oxysporum, Aspergillus sclerotiorum, Aspergillus niger). The compounds 3f, 3g, 4f & 4g were found to be significantly active against the tested microorganisms. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.06.030
• 作为产物：
  描述：

  1,10-二溴癸烷 、 间羟基苯甲醛 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以62%的产率得到1,10-bis(3-formylphenoxy)decane
  参考文献：
  名称：

  利用Scholl反应扩展应变的Benzenoid大环的π扩展

  摘要：

  已经合成了一系列弯曲的含对叔丁基的大环，然后进行区域选择性溴化，芳基化，然后进行基于Scholl的环脱氢反应。这些大环的烷氧基桥连单元的缩短增加了对-三联苯单元的弯曲，以及中心对-亚苯环体系的应变能（SE）。第一次，利用Scholl反应，在π扩展到应变多环芳烃体系的π扩展的背景下，研究了这类苯环化合物的大环结构SE的增量增加。

  DOI：

  10.1021/acs.orglett.8b02979

文献信息

• Synthesis, Antimicrobial Evaluations, and DNA Photo Cleavage Studies of New Bispyranopyrazoles
  作者：Mohamad Yusuf、Manvinder Kaur、Harvinder Singh Sohal

  DOI：10.1002/jhet.2530

  日期：2017.1

  13C‐NMR, and ESI‐MS). The newly prepared compounds were screened for their antimicrobial activity against seven bacterial and five fungal strains. The DNA photo cleavage potential of these compounds was also evaluated by using agarose gel electrophoresis, and bispyranopyrazoles 4b, 4d and 4e exhibited significant level of DNA photocleavage activity.

  双苯并吡唑（4a，4b，4c，4d，4e，4f，4g）是由苯甲醛（2a，2b，2c，2d，2e，2f，2g）与3-甲基吡唑-5-酮3反应合成的和丙二腈在酒精介质中回流。二苯甲醛是在碱性条件下，在干燥的EtOH / DMF存在下，由3-羟基苯甲醛与合适的1，ω-二溴代烷烃进行O-烷基化反应而获得的。双环化合物的结构是通过对其光谱参数（IR，1 H-NMR，13 C-NMR和ESI-MS）进行严格分析而确定的。筛选了新制备的化合物对七种细菌和五种真菌菌株的抗菌活性。还通过使用琼脂糖凝胶电泳评估了这些化合物的DNA光裂解潜力，并且双吡喃并吡唑4b，4d和4e表现出显着水平的DNA光裂解活性。
• Self-assembly of molecular devices containing a ferrocene, a porphyrin and a quinone in a triple macrocyclic architecture
  作者：Richard W. Wagner、Philip A. Brown、Thomas E. Johnson、Jonathan S. Lindsey

  DOI：10.1039/c39910001463

  日期：——

  Porphyrinogen self-assembly is compatible with a structurally diverse set of meta-linked dialdehyde building blocks, providing rapid access under gentle conditions to porphyrins bearing redox-active units positioned in a 3-dimensional architecture.

  卟啉原自组装与结构多样的元链二甲醛结构单元兼容，可在温和的条件下快速获得具有氧化还原活性单元的三维结构卟啉。
• Investigation of the one-flask synthesis of porphyrins bearing meso-linked straps of variable length, rigidity, and redox activity
  作者：Richard W. Wagner、Thomas E. Johnson、Jonathan S. Lindsey

  DOI：10.1016/s0040-4020(97)00327-x

  日期：1997.5

  The reactions of 18 dialdehydes have been examined in the two-step one-flask room temperature porphyrin synthesis. Efficient alkylation methods were established for the reaction of diols and diacids with m-bromomethylbenzaldehyde Dialdehydes linked at the o,o'- or m,m'-positions were converted to strapped porphyrins in yields up to 25%, while the one p,p'-linked dialdehyde that was examined failed to give porphyrin. The resulting porphyrins bear straps joining adjacent meso-positions rather than across the face of the porphyrin. Dialdehydes incorporating rigid groups provided improved yields in some but not all cases. The yield of strapped porphyrin exhibited a maximum at 10(-2) M reactant concentrations. The o,o'-strapped porphyrins exist as atropisomers thai are sufficiently stable to interconversion at room temperature to be separable chromatographically. No atropisomers of m,m'-strapped porphyrins could be separated, though some could be observed by H-1 NMR spectroscopy. For two different m,m'-strapped porphyrins, the Delta G double dagger values for interconversion of the atropisomers were found to be 66 and 68 kJ/mol. The outer rings in these strapped porphyrins range in size from 14 to 24 atoms. Five porphyrins with bridging redox-active groups (ferrocene or anthraquinone) have been prepared in one-flask reactions, including a porphyrin bearing one ferrocene and one anthraquinone in straps across adjacent meta-substituted phenyl sites. (C) 1997 Elsevier Science Ltd.
• 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.