4-((4-hydroxyphenyl)ethynyl)benzaldehyde | 863333-36-2

• 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: 4-((4-hydroxyphenyl)ethynyl)benzaldehyde
• 英文别名: 4-[2-(4-Hydroxyphenyl)ethynyl]benzaldehyde
• CAS: 863333-36-2
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: MZOJGKPESRJQTR-UHFFFAOYSA-N

物化性质

• 沸点：
  422.5±30.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-((4-hydroxyphenyl)ethynyl)benzaldehyde 在 potassium carbonate 、 溶剂黄146 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 4-[(4-{[4-({4-[2-(morpholin-4-yl)ethyl]piperazin-1-yl}methyl)phenyl]ethynyl}phenoxy)methyl]tetrahydro-2H-pyran-4-carboxylic acid
  参考文献：
  名称：

  Synthesis, Structure, and SAR of Tetrahydropyran-Based LpxC Inhibitors

  摘要：

  In the search for novel Gram-negative agents, we performed a comprehensive search of the AstraZeneca collection and identified a tetrahydropyran-based matrix metalloprotease (MMP) inhibitor that demonstrated nanomolar inhibition of UDP-3-O-(acyl)-N-acetylglucosamine deacetylase (LpxC). Crystallographic studies in Aquifex aeolicus LpxC indicated the tetrahydropyran engaged in the same hydrogen bonds and van der Waals interactions as other known inhibitors. Systematic optimization of three locales on the scaffold provided compounds with improved Gram-negative activity. However, the optimization of LpxC activity was not accompanied by reduced inhibition of MMPs. Comparison of the crystal structure of the native product, UDP-3-O-(acyl)-glucosamine, in Aquifex aeolicus to the structure of a tetrahydropyran-based inhibitor indicates pathways for future optimization.

  DOI：

  10.1021/ml500210x
• 作为产物：
  描述：

  4-[(tetrahydro-2H-pyran-2-yl)oxy]iodobenzene 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 4-((4-hydroxyphenyl)ethynyl)benzaldehyde
  参考文献：
  名称：

  Synthesis, Structure, and SAR of Tetrahydropyran-Based LpxC Inhibitors

  摘要：

  In the search for novel Gram-negative agents, we performed a comprehensive search of the AstraZeneca collection and identified a tetrahydropyran-based matrix metalloprotease (MMP) inhibitor that demonstrated nanomolar inhibition of UDP-3-O-(acyl)-N-acetylglucosamine deacetylase (LpxC). Crystallographic studies in Aquifex aeolicus LpxC indicated the tetrahydropyran engaged in the same hydrogen bonds and van der Waals interactions as other known inhibitors. Systematic optimization of three locales on the scaffold provided compounds with improved Gram-negative activity. However, the optimization of LpxC activity was not accompanied by reduced inhibition of MMPs. Comparison of the crystal structure of the native product, UDP-3-O-(acyl)-glucosamine, in Aquifex aeolicus to the structure of a tetrahydropyran-based inhibitor indicates pathways for future optimization.

  DOI：

  10.1021/ml500210x

文献信息

• Systematic Investigation of Silver-Carbon Bonding in Coordination Frameworks with Aryl Ligands That Contain Ethynyl and Ethenyl Substituents
  作者：Sam C. K. Hau、Thomas C. W. Mak

  DOI：10.1002/chem.201204225

  日期：2013.4.22

  e complexes that contained designed ligands, each of which was composed of an aromatic system that was functionalized with terminal and internal ethynyl groups and a vinyl substituent, provided detailed information on the influence of ligand disposition and orientation, coordination preferences, and the co‐existence of different types of silver(I)–carbon bonding interactions (silver–ethynide, silver–ethynyl

  一系列十种包含设计的配体的晶体的单晶X射线衍射，这些配合物包含设计的配体，每个配体均由芳香族系统组成，该系统经末端和内部乙炔基团以及乙烯基取代基官能化，提供了详细信息有关配体位置和方向，配位偏好以及不同类型的银（I）-碳键相互作用（银-乙炔，银-乙炔基，银-乙烯基和银-芳族化合物）共存影响的信息亲和性和弱分子间/分子间相互作用巩固了协调网络的建设。复杂的Ag L10⋅ 6的AgCF 3 CO 2 ⋅ ħ 2 ö ⋅MeOH（HL10 = 1-[4-（丙-2-炔氧基）-3-乙烯基苯基]乙炔基}萘）是第一个报告的实例，在固态时表现出所有四种银（I）-碳键相互作用。