methyl 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazole-4-carboxylate | 1096535-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazole-4-carboxylate
• 英文别名: methyl 2-[1-[tert-butyl(dimethyl)silyl]oxy-7-phenylheptyl]-1,3-oxazole-4-carboxylate
• CAS: 1096535-87-3
• 化学式: C₂₄H₃₇NO₄Si
• 分子量: 431.648
• InChiKey: MJIHWMCUBLDKFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazole-4-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以84%的产率得到methyl 2-(1-hydroxy-7-phenylheptyl)oxazole-4-carboxylate
  参考文献：
  名称：

  Exploration of a fundamental substituent effect of α-ketoheterocycle enzyme inhibitors: Potent and selective inhibitors of fatty acid amide hydrolase

  摘要：

  A series of C4 substituted alpha-ketooxazoles were examined as inhibitors of the serine hydrolase fatty acid amide hydrolase in efforts that further de. ne and generalize a fundamental substituent effect on enzyme inhibitory potency. Thus, a plot of the Hammett sigma(m) versus -log K-i provided a linear correlation (R-2 = 0.90) with a slope of 3.37 (rho = 3.37), that is of a magnitude that indicates that of the electron-withdrawing character of the substituent dominates its effects (a one unit change in sigma(m) provides a > 1000-fold change in Ki). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.084
• 作为产物：
  描述：

  氰基甲酸甲酯 、 4-bromo-2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazole 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.03h， 以37%的产率得到methyl 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazole-4-carboxylate
  参考文献：
  名称：

  Exploration of a fundamental substituent effect of α-ketoheterocycle enzyme inhibitors: Potent and selective inhibitors of fatty acid amide hydrolase

  摘要：

  A series of C4 substituted alpha-ketooxazoles were examined as inhibitors of the serine hydrolase fatty acid amide hydrolase in efforts that further de. ne and generalize a fundamental substituent effect on enzyme inhibitory potency. Thus, a plot of the Hammett sigma(m) versus -log K-i provided a linear correlation (R-2 = 0.90) with a slope of 3.37 (rho = 3.37), that is of a magnitude that indicates that of the electron-withdrawing character of the substituent dominates its effects (a one unit change in sigma(m) provides a > 1000-fold change in Ki). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.084
• 作为试剂：
  描述：

  4-bromo-2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazole 、 氰基甲酸甲酯 在 methyl 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazole-4-carboxylate 作用下， 以Flash chromatography (10% EtOAc/hexanes) yielded 3j as a colorless oil (9.5 mg, 37%)的产率得到
  参考文献：
  名称：

  C4-SUBSTITUTED ALPHA-KETO OXAZOLES

  摘要：

  本发明提供了一系列C4取代的噁唑化合物，其在2位具有α酮侧链，例如，式I的化合物。这些化合物可以抑制脂肪酸酰胺水解酶，并可用于治疗由脂肪酸酰胺水解酶调节的疾病。本发明还提供了制备式I化合物的方法，用于制备式I化合物的有用中间体，以及使用式1化合物及其组成物的方法。

  公开号：

  US20120302607A1