4-(3-(4-cyanophenoxy)propoxy)benzaldehyde | 1075750-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3-(4-cyanophenoxy)propoxy)benzaldehyde
• CAS: 1075750-63-8
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: PNZZUHDIQVETJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  59.32
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(3-(4-cyanophenoxy)propoxy)benzaldehyde 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 120.0h， 生成 5-(4-(3-(4-(((9-anthracenyl)methylamino)methyl)phenoxy)propoxy)benzylamino)pentan-1-ol
  参考文献：
  名称：

  Chelate Cooperativity and Spacer Length Effects on the Assembly Thermodynamics and Kinetics of Divalent Pseudorotaxanes

  摘要：

  Homo- and heterodivalent crown-ammonium pseudorotaxanes with different spacers connecting the two axle ammonium binding sites have been synthesized and characterized by NMR spectroscopy and ESI mass spectrometry. The homodivalent pseudorotaxanes are investigated with respect to the thermodynamics of divalent binding and to chelate cooperativity. The shortest spacer exhibits a chelate cooperativity much stronger than that of the longer spacers. On the basis of crystal structure, this can be explained by a noninnocent spacer, which contributes to the binding strength in addition to the two binding sites. Already very subtle changes in the spacer length, i.e., the introduction of an additional methylene group, cause substantial changes in the magnitude of cooperative binding as expressed in the large differences in effective molarity. With a similar series of heterodivalent pseudorotaxanes, the spacer effects on the barrier for the intramolecular threading step has been examined with the result that the shortest spacer causes a strained transition structure and thus the second binding event occurs slower than that of the longer spacers. The activation enthalpies and entropies show clear trends. While the longer spacers reduce the enthalpic strain that is present in the transition state for the shortest member of the series, the longer spacers become entropically slightly more unfavorable because of conformational fixation of the spacer chain during the second binding event. These results clearly show the noninnocent spacers to complicate the analysis of multivalent binding. An approximate description which considers the binding sites to be connected just by a flexible chain turns out to be more a rough approximation than a good model. The second conclusion from the results presented here is that multivalency is expressed in both the thermodynamics and the kinetics in different ways. A spacer optimized for strong binding is suboptimal for fast pseudorotaxane formation.

  DOI：

  10.1021/ja2107096
• 作为产物：
  描述：

  4-(3-溴丙基氧基)苯甲醛 、 4-羟基苯甲腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(3-(4-cyanophenoxy)propoxy)benzaldehyde
  参考文献：
  名称：

  基于巴比妥酸的新型PPARgamma配体：虚拟筛选，合成和受体结合研究。

  摘要：

  利用虚拟筛选和分子对接方法，设计了一系列基于巴比妥酸（BA）的PPARγ配体。为了验证计算方法，合成了设计的分子并在体外放射性配体结合研究中进行了评估。在全部14个分子中，发现有6个与鼠PPARgamma结合，与参考标准吡格列酮相比，IC（50）的范围为0.1至2.5 microM（IC（50）= 0.7 microM）。

  DOI：

  10.1016/j.bmcl.2008.08.028