{4-(methylethylidene)-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}methyl 4-[2-(4-ethynylphenyl)ethynyl]benzoate | 932711-38-1

• 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-(methylethylidene)-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}methyl 4-[2-(4-ethynylphenyl)ethynyl]benzoate
• 英文别名: [5-Oxo-2-(phenylmethoxymethyl)-4-propan-2-ylideneoxolan-2-yl]methyl 4-[2-(4-ethynylphenyl)ethynyl]benzoate
• CAS: 932711-38-1
• 化学式: C₃₃H₂₈O₅
• 分子量: 504.582
• InChiKey: QPONTFRTRZWWFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {4-(methylethylidene)-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}methyl 4-[2-(4-ethynylphenyl)ethynyl]benzoate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三氯化硼 、 caesium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 [2-(Hydroxymethyl)-5-oxo-4-propan-2-ylideneoxolan-2-yl]methyl 4-[2-[4-[4-[4-[2-[4-[[2-(hydroxymethyl)-5-oxo-4-propan-2-ylideneoxolan-2-yl]methoxycarbonyl]phenyl]ethynyl]phenyl]buta-1,3-diynyl]phenyl]ethynyl]benzoate
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol (DAG). 27. Modulation of Membrane Translocation of Protein Kinase C (PKC) Isozymes α and δ by Diacylglycerol Lactones (DAG-lactones) Containing Rigid-Rod Acyl Groups

  摘要：

  Highly rigid and geometrically well-defined rods composed of ethynylene-substituted aromatic spacers [oligo(p-phenyleneethynylene), OPE] were incorporated as acyl moieties on diacylglycerol lactones (DAG-lactones) and investigated for their ability to bind to protein kinase C (PKC) and translocate PKC alpha and delta isoforms to plasma and internal membranes. The kinetics of PKC translocation were correlated with biological responses, viz. ERK phosphorylation, induction of IL-6 secretion, inhibition of cell proliferation, and induction of cellular attachment, that display very different time courses. Because OPE rods assemble through noncovalent forces and form stable films, they may influence the microdomain environment around the DAG-lactone membrane-binding site. A comparison of two DAG-lactones (1 and 10), one with two PE units (1) and the other with an equivalent flexible acyl chain (10) of matching lipophilicity, clearly demonstrated the effect of the rigid OPE chain in substantially prolonging the translocated state of both PKC alpha and delta.

  DOI：

  10.1021/jm061289j
• 作为产物：
  描述：

  4-((4-乙炔苯基)乙炔)苯甲酸 、 5-((苄氧基)甲基)-5-(羟甲基)-3-(丙烷-2-亚基)二氢呋喃-2(3H)-酮 在 4-二甲氨基吡啶 、 双(2-氧代-3-恶唑烷基)次磷酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以25 mg的产率得到{4-(methylethylidene)-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}methyl 4-[2-(4-ethynylphenyl)ethynyl]benzoate
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol (DAG). 27. Modulation of Membrane Translocation of Protein Kinase C (PKC) Isozymes α and δ by Diacylglycerol Lactones (DAG-lactones) Containing Rigid-Rod Acyl Groups

  摘要：

  Highly rigid and geometrically well-defined rods composed of ethynylene-substituted aromatic spacers [oligo(p-phenyleneethynylene), OPE] were incorporated as acyl moieties on diacylglycerol lactones (DAG-lactones) and investigated for their ability to bind to protein kinase C (PKC) and translocate PKC alpha and delta isoforms to plasma and internal membranes. The kinetics of PKC translocation were correlated with biological responses, viz. ERK phosphorylation, induction of IL-6 secretion, inhibition of cell proliferation, and induction of cellular attachment, that display very different time courses. Because OPE rods assemble through noncovalent forces and form stable films, they may influence the microdomain environment around the DAG-lactone membrane-binding site. A comparison of two DAG-lactones (1 and 10), one with two PE units (1) and the other with an equivalent flexible acyl chain (10) of matching lipophilicity, clearly demonstrated the effect of the rigid OPE chain in substantially prolonging the translocated state of both PKC alpha and delta.

  DOI：

  10.1021/jm061289j