2-[(4-methoxyphenoxy)methyl]-5-[5-methyl-3-(2-methylpropyl)hexylidene]-2-[(phenylmethoxy)methyl]-1,3-dioxolan-4-one | 946570-47-4

• 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: 2-[(4-methoxyphenoxy)methyl]-5-[5-methyl-3-(2-methylpropyl)hexylidene]-2-[(phenylmethoxy)methyl]-1,3-dioxolan-4-one
• 英文别名: 2-[(4-methoxyphenoxy)methyl]-5-[5-methyl-3-(2-methylpropyl)hexylidene]-2-(phenylmethoxymethyl)-1,3-dioxolan-4-one
• CAS: 946570-47-4
• 化学式: C₃₀H₄₀O₆
• 分子量: 496.644
• InChiKey: VIXMBQIECZRTAA-UHFFFAOYSA-N

物化性质

• 沸点：
  623.5±50.0 °C(predicted)
• 密度：
  1.101±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  36.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-[(4-methoxyphenoxy)methyl]-5-[5-methyl-3-(2-methylpropyl)hexylidene]-2-[(phenylmethoxy)methyl]-1,3-dioxolan-4-one 在 4-二甲氨基吡啶 吡啶 、 ammonium cerium(IV) nitrate 、 三氯化硼 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 {2-(hydroxymethyl)-5-[5-methyl-3-(2-methylpropyl)hexylidene]-4-oxo-1,3-dioxolan-2-yl}methyl 3-methylbutanoate
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol (DAG). 28. DAG-dioxolanones Reveal a New Additional Interaction Site in the C1b Domain of PKCδ

  摘要：

  Diacylglycerol (DAG) lactones have provided a powerful platform for structural exploration of the interactions between ligands and the C1 domains of protein kinase C (PKC). In this study, we report that DAG-dioxolanones, novel derivatives of DAG-lactones, exploit an additional point of contact (glutamine 27) in their binding with the C1b domain of PKC delta. Mutation of this point of contact to glutamate selectively impairs binding of the DAG-dioxolanones compared to that of the corresponding DAG-lactones (1200- to 3000-fold versus 35- to 55-fold, respectively). The differential response of this mutated C1b domain to the DAG-dioxolanones relative to the DAG-lactones provides a unique tool to probe the role of the C1b domain in PKC delta function, where the response to the DAG-lactones affords a positive control for retained function. Using this approach, we show that the C1b domain of PKC delta plays the predominant role in the translocation of PKC delta to the membrane in the presence of DAG.

  DOI：

  10.1021/jm0702579
• 作为产物：
  描述：

  1-({4-(chloromethyl)-2-[(phenylmethoxy)methyl](1,3-dioxolan-2-yl)}methoxy)-4-methoxybenzene 在 potassium tert-butylate 、 臭氧 、 甲基磺酰氯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 2-[(4-methoxyphenoxy)methyl]-5-[5-methyl-3-(2-methylpropyl)hexylidene]-2-[(phenylmethoxy)methyl]-1,3-dioxolan-4-one
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol (DAG). 28. DAG-dioxolanones Reveal a New Additional Interaction Site in the C1b Domain of PKCδ

  摘要：

  Diacylglycerol (DAG) lactones have provided a powerful platform for structural exploration of the interactions between ligands and the C1 domains of protein kinase C (PKC). In this study, we report that DAG-dioxolanones, novel derivatives of DAG-lactones, exploit an additional point of contact (glutamine 27) in their binding with the C1b domain of PKC delta. Mutation of this point of contact to glutamate selectively impairs binding of the DAG-dioxolanones compared to that of the corresponding DAG-lactones (1200- to 3000-fold versus 35- to 55-fold, respectively). The differential response of this mutated C1b domain to the DAG-dioxolanones relative to the DAG-lactones provides a unique tool to probe the role of the C1b domain in PKC delta function, where the response to the DAG-lactones affords a positive control for retained function. Using this approach, we show that the C1b domain of PKC delta plays the predominant role in the translocation of PKC delta to the membrane in the presence of DAG.

  DOI：

  10.1021/jm0702579