2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-4-(methylthio)oxazole | 1096535-75-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-4-(methylthio)oxazole
• 英文别名: tert-butyl-dimethyl-[1-(4-methylsulfanyl-1,3-oxazol-2-yl)-7-phenylheptoxy]silane
• CAS: 1096535-75-9
• 化学式: C₂₃H₃₇NO₂SSi
• 分子量: 419.704
• InChiKey: BHVVFQGYFGKTLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.65
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-4-(methylthio)oxazole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以90%的产率得到1-(4-(methylthio)oxazol-2-yl)-7-phenylheptan-1-ol
  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：

  二甲基二硫 、 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41%的产率得到2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-4-(methylthio)oxazole
  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 、 二甲基二硫 在 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-4-(methylthio)oxazole 作用下， 以Preparative TLC (7% EtOAc/hexanes) yielded 3f as a colorless oil (12.7 mg, 41%)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

文献信息

• Exploration of a fundamental substituent effect of α-ketoheterocycle enzyme inhibitors: Potent and selective inhibitors of fatty acid amide hydrolase
  作者：Jessica K. DeMartino、Joie Garfunkle、Dustin G. Hochstatter、Benjamin F. Cravatt、Dale L. Boger

  DOI：10.1016/j.bmcl.2008.06.084

  日期：2008.11

  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.
• C4-SUBSTITUTED ALPHA-KETO OXAZOLES
  申请人：Boger Dale L.

  公开号：US20120302607A1

  公开（公告）日：2012-11-29

  The invention provides a series of C4-substituted oxazole compounds having an alpha keto side chain at the 2 position, for example, compounds of formula I. The compounds can inhibit fatty acid amide hydrolase and can be useful for treatment of malconditions modulated by fatty acid amide hydrolase. The invention further provides methods of making compounds of formula I, useful intermediates in the preparation of compounds of formula I, and methods of using compounds of formula 1 and compositions thereof.

  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。