methyl (2S)-2-[[3-[4-[tert-butyl(dimethyl)silyl]oxybutyl]-4,5-dihydro-1,2-oxazol-5-yl]methylideneamino]-3-methylbutanoate | 135147-34-1

• 分子结构分类: 有机化合物
• 英文名称: methyl (2S)-2-[[3-[4-[tert-butyl(dimethyl)silyl]oxybutyl]-4,5-dihydro-1,2-oxazol-5-yl]methylideneamino]-3-methylbutanoate
• CAS: 135147-34-1；135147-35-2
• 化学式: C₂₀H₃₈N₂O₄Si
• 分子量: 398.618
• InChiKey: LQVWQBTZXJLEFJ-ZVAWYAOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  27.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  69.48
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[3-[4-[tert-butyl(dimethyl)silyl]oxybutyl]-4,5-dihydro-1,2-oxazol-5-yl]methylideneamino]-3-methylbutanoate 在 W-2 Raney nickel 四丁基氟化铵 、 水 、 氢气 、 叔丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.83h， 生成 N-<8-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-hydroxy-4-oxo-1-(1H-pyrrol-3-yl)octyl>-N-formyl-L-valine methyl ester
  参考文献：
  名称：

  Synthesis of structural analogs of lyngbyatoxin A and their evaluation as activators of protein kinase C

  摘要：

  Syntheses of several new analogues of lyngbyatoxin A from a single common intermediate are described. These compounds bear a carbon chain at the 7-position of the indolactam V (ILV) nucleus which contains either a hydrophilic or a lipophilic group. The effect of these minor structural alterations on the ability of the ILV analogues to activate the enzyme protein kinase C (PKC) was determined by measuring the extent of phosphorylation of calf thymus histone (III-S). Introduction of a hydroxyl group on the C-7 appendage was found to dramatically decrease compound 3's ability to activate PKC. This result is interpreted in terms of the decreased ability of 3 to associate with the membrane bilayer.

  DOI：

  10.1021/jm00112a017
• 作为产物：
  描述：

  在 咪唑 、 硫酸 、 magnesium sulfate 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 5.0h， 生成 methyl (2S)-2-[[3-[4-[tert-butyl(dimethyl)silyl]oxybutyl]-4,5-dihydro-1,2-oxazol-5-yl]methylideneamino]-3-methylbutanoate
  参考文献：
  名称：

  Synthesis of structural analogs of lyngbyatoxin A and their evaluation as activators of protein kinase C

  摘要：

  Syntheses of several new analogues of lyngbyatoxin A from a single common intermediate are described. These compounds bear a carbon chain at the 7-position of the indolactam V (ILV) nucleus which contains either a hydrophilic or a lipophilic group. The effect of these minor structural alterations on the ability of the ILV analogues to activate the enzyme protein kinase C (PKC) was determined by measuring the extent of phosphorylation of calf thymus histone (III-S). Introduction of a hydroxyl group on the C-7 appendage was found to dramatically decrease compound 3's ability to activate PKC. This result is interpreted in terms of the decreased ability of 3 to associate with the membrane bilayer.

  DOI：

  10.1021/jm00112a017