1,7-bis(3-formylphenoxy)heptane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,7-bis(3-formylphenoxy)heptane
• 英文别名: 3-[7-(3-Formylphenoxy)heptoxy]benzaldehyde；3-[7-(3-formylphenoxy)heptoxy]benzaldehyde
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: PMYMVSABDMKJAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1,7-bis(3-formylphenoxy)heptane 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成
  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
• 作为产物：
  描述：

  1,7-二溴庚烷 、 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72%的产率得到1,7-bis(3-formylphenoxy)heptane
  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

• 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.
• π-Extension of Strained Benzenoid Macrocycles Using the Scholl Reaction
  作者：Nirob K. Saha、Nirmal K. Mitra、Kara F. Johnson、Bradley L. Merner

  DOI：10.1021/acs.orglett.8b02979

  日期：2018.11.2

  reaction. Shortening the alkyloxy bridging unit of these macrocycles increases the bend in the p-terphenyl unit, as well as the strain energy (SE) of the central para-phenylene ring system. For the first time, incremental increases in SE of the macrocyclic structure of this class of benzenoid compounds have been investigated in the context of π-extension to strained polycyclic aromatic hydrocarbon systems

  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。