(E/Z)-{4-[5-methyl-3-(2-methylpropyl)hexylidene]-2-[(phenylmethoxy)methyl]-2-2,3,5-trihydrofuryl}methyl 2,2-dimethylpropanoate | 862549-20-0

• 分子结构分类: 有机化合物
• 英文名称: (E/Z)-{4-[5-methyl-3-(2-methylpropyl)hexylidene]-2-[(phenylmethoxy)methyl]-2-2,3,5-trihydrofuryl}methyl 2,2-dimethylpropanoate
• CAS: 862549-20-0
• 化学式: C₂₉H₄₆O₄
• 分子量: 458.682
• InChiKey: PPRDTRCILIETKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  33.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E/Z)-{4-[5-methyl-3-(2-methylpropyl)hexylidene]-2-[(phenylmethoxy)methyl]-2-2,3,5-trihydrofuryl}methyl 2,2-dimethylpropanoate 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以60%的产率得到(E/Z)-{2-(hydroxymethyl)-4-[5-methyl-3-(2-methylpropyl)hexylidene]-2-2,3,5-trihydrofuryl}methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol (DAG). 25. Exploration of the sn-1 and sn-2 Carbonyl Functionality Reveals the Essential Role of the sn-1 Carbonyl at the Lipid Interface in the Binding of DAG-Lactones to Protein Kinase C

  摘要：

  Diacylglycerol (DAG) lactones with altered functionality (C=O -> CH2 or C=O -> C=S) at the sn-1 and sn-2 carbonyl pharmacophores were synthesized and used as probes to dissect the individual role of each carbonyl in the binding to protein kinase C (PKC). The results suggest that the hydrated sn-1 carbonyl is engaged in very strong hydrogen-bonding interactions with the charged lipid headgroups and organized water molecules at the lipid interface. Conversely, the sn-2 carbonyl has a more modest contribution to the binding process as a result of its involvement with the receptor (Cl domain) via conventional hydrogen bonding to the protein. The parent DAG-lactones, E-6 and Z-7, were designed to bind exclusively in the sn-2 binding mode to ensure the correct orientation and disposition of pharmacophores at the binding site.

  DOI：

  10.1021/jm050352m
• 作为产物：
  描述：

  二异丁基酮 在 palladium on activated charcoal 咪唑 、 lithium aluminium tetrahydride 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 4 A molecular sieve 、 氢气 、 碘 、 三乙胺 、 三苯基膦 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 56.17h， 生成 (E/Z)-{4-[5-methyl-3-(2-methylpropyl)hexylidene]-2-[(phenylmethoxy)methyl]-2-2,3,5-trihydrofuryl}methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol (DAG). 25. Exploration of the sn-1 and sn-2 Carbonyl Functionality Reveals the Essential Role of the sn-1 Carbonyl at the Lipid Interface in the Binding of DAG-Lactones to Protein Kinase C

  摘要：

  Diacylglycerol (DAG) lactones with altered functionality (C=O -> CH2 or C=O -> C=S) at the sn-1 and sn-2 carbonyl pharmacophores were synthesized and used as probes to dissect the individual role of each carbonyl in the binding to protein kinase C (PKC). The results suggest that the hydrated sn-1 carbonyl is engaged in very strong hydrogen-bonding interactions with the charged lipid headgroups and organized water molecules at the lipid interface. Conversely, the sn-2 carbonyl has a more modest contribution to the binding process as a result of its involvement with the receptor (Cl domain) via conventional hydrogen bonding to the protein. The parent DAG-lactones, E-6 and Z-7, were designed to bind exclusively in the sn-2 binding mode to ensure the correct orientation and disposition of pharmacophores at the binding site.

  DOI：

  10.1021/jm050352m