methyl 2-[[(2E,6E)-8-[tert-butyl(dimethyl)silyl]oxy-2,6-dimethylocta-2,6-dienyl]amino]benzoate | 798573-58-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 2-[[(2E,6E)-8-[tert-butyl(dimethyl)silyl]oxy-2,6-dimethylocta-2,6-dienyl]amino]benzoate
• CAS: 798573-58-7
• 化学式: C₂₄H₃₉NO₃Si
• 分子量: 417.664
• InChiKey: VIYKEPGHWXNLQJ-SQWGNMLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-[[(2E,6E)-8-[tert-butyl(dimethyl)silyl]oxy-2,6-dimethylocta-2,6-dienyl]amino]benzoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到methyl 2-((2E,6E)-8-hydroxy-2,6-dimethyl-octa-2,6-dienylamino)benzoate
  参考文献：
  名称：

  Synthesis and Activity of Fluorescent Isoprenoid Pyrophosphate Analogues

  摘要：

  New fluorescent analogues of farnesol and geranylgeraniol have been prepared and then converted to the corresponding pyrophosphates. These analogues incorporate anthranylate or dansyl-like groups anchored to the terpenoid skeleton through amine bonds that would be expected to be relatively stable to metabolism. After addition of the alcohols or the pyrophosphates to the culture medium, their fluorescence is readily observed inside a human-derived leukemia cell line. Enzyme assays have revealed that the farnesyl pyrophosphate analogue is an inhibitor of FTase, while the corresponding alcohol is not. These results, together with Western blot analyses of cell lysates, indicate that the farnesyl pyrophosphate analogue penetrates the cells as an intact pyrophosphate and that it does so at a biologically relevant concentration.

  DOI：

  10.1021/jo049101w
• 作为产物：
  描述：

  (2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate 在 potassium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 7.28h， 生成 methyl 2-[[(2E,6E)-8-[tert-butyl(dimethyl)silyl]oxy-2,6-dimethylocta-2,6-dienyl]amino]benzoate
  参考文献：
  名称：

  Synthesis and Activity of Fluorescent Isoprenoid Pyrophosphate Analogues

  摘要：

  New fluorescent analogues of farnesol and geranylgeraniol have been prepared and then converted to the corresponding pyrophosphates. These analogues incorporate anthranylate or dansyl-like groups anchored to the terpenoid skeleton through amine bonds that would be expected to be relatively stable to metabolism. After addition of the alcohols or the pyrophosphates to the culture medium, their fluorescence is readily observed inside a human-derived leukemia cell line. Enzyme assays have revealed that the farnesyl pyrophosphate analogue is an inhibitor of FTase, while the corresponding alcohol is not. These results, together with Western blot analyses of cell lysates, indicate that the farnesyl pyrophosphate analogue penetrates the cells as an intact pyrophosphate and that it does so at a biologically relevant concentration.

  DOI：

  10.1021/jo049101w