(4S)-4-benzyl-3-[(2S)-2-bromopropanoyl]-1,3-oxazolidin-2-one | 114341-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-4-benzyl-3-[(2S)-2-bromopropanoyl]-1,3-oxazolidin-2-one
• CAS: 114341-79-6
• 化学式: C₁₃H₁₄BrNO₃
• 分子量: 312.163
• InChiKey: WMEFKODGDLZACH-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-二氢-2-苯基恶唑 、 (4S)-4-benzyl-3-[(2S)-2-bromopropanoyl]-1,3-oxazolidin-2-one 在 (p-伞花烃)双(均三甲苯羧基)钌(II) 、 potassium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以57%的产率得到
  参考文献：
  名称：

  一锅钌（II / III）催化的连续间位-/邻位-C-H官能化

  摘要：

  顺序双重元-C–H /邻位-C–H官能化是通过多官能钌（II）双羧酸钌催化实现的。在合成有用的酰亚胺的帮助下，一氧化碳的双重活化被证明是一锅法可行的。操作简单的双重C–H官能化在高水平的位置选择性控制下发生，是通过明智地选择反应温度以非顺序方式进行的。详细的实验机理研究，包括空前的电子顺磁共振（EPR）实验，为均相C–X键断裂和便捷的C–H钌化提供了有力的支持，而计算密度泛函理论（DFT）分析则为涉及以下方面的新型机理提供了支持通过环金属化钌（III）配合物作为关键中间体的协同催化。

  DOI：

  10.1021/acscatal.7b03648
• 作为产物：
  描述：

  (S)-4-苄基-2-唑烷酮 、 2-溴丙酰溴 在 正丁基锂 作用下， 生成 (4S)-4-benzyl-3-[(2S)-2-bromopropanoyl]-1,3-oxazolidin-2-one 、 (4S)-4-benzyl-3-[(2R)-2-bromopropanoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A₂. 3. Indole-3-glyoxamides

  摘要：

  The preceding papers of this series detail the development of functionalized indole-3-acetamides as inhibitors of hnps-PLA(2). We describe here the extension of the structure-activity relationship to include a series of indole-3-glyoxamide derivatives. Functionalized indole-3-glyoxamides with an acidic substituent appended to the 4- or 5-position of the indole ring were prepared and tested as inhibitors of hnps-PLA(2). It was found that the indole-3-glyoxamides with a 4-oxyacetic acid substituent had optimal inhibitory activity. These inhibitors exhibited an improvement in potency over the best of the indole-3-acetamides, and LY315920 (6m) was selected for evaluation clinically as an hnps-PLA(2) inhibitor.

  DOI：

  10.1021/jm960487f

文献信息

• Sequential <i>meta</i>-/<i>ortho</i>-C–H Functionalizations by One-Pot Ruthenium(II/III) Catalysis
  作者：Korkit Korvorapun、Nikolaos Kaplaneris、Torben Rogge、Svenja Warratz、A. Claudia Stückl、Lutz Ackermann

  DOI：10.1021/acscatal.7b03648

  日期：2018.2.2

  Sequential twofold meta-C–H/ortho-C–H functionalization was achieved by means of versatile ruthenium(II) biscarboxylate catalysis. The double C–H activation proved viable in a one-pot fashion with the assistance of synthetically useful imidates. The operationally simple twofold C–H functionalization occurred with high levels of positional selectivity control and was conducted in a nonsequential manner

  顺序双重元-C–H /邻位-C–H官能化是通过多官能钌（II）双羧酸钌催化实现的。在合成有用的酰亚胺的帮助下，一氧化碳的双重活化被证明是一锅法可行的。操作简单的双重C–H官能化在高水平的位置选择性控制下发生，是通过明智地选择反应温度以非顺序方式进行的。详细的实验机理研究，包括空前的电子顺磁共振（EPR）实验，为均相C–X键断裂和便捷的C–H钌化提供了有力的支持，而计算密度泛函理论（DFT）分析则为涉及以下方面的新型机理提供了支持通过环金属化钌（III）配合物作为关键中间体的协同催化。
• Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A₂. 3. Indole-3-glyoxamides
  作者：Susan E. Draheim、Nicholas J. Bach、Robert D. Dillard、Dennis R. Berry、Donald G. Carlson、Nickolay Y. Chirgadze、David K. Clawson、Lawrence W. Hartley、Lea M. Johnson、Noel D. Jones、Emma R. McKinney、Edward D. Mihelich、Jennifer L. Olkowski、Richard W. Schevitz、Amy C. Smith、David W. Snyder、Cynthia D. Sommers、Jean-Pierre Wery

  DOI：10.1021/jm960487f

  日期：1996.1.1

  The preceding papers of this series detail the development of functionalized indole-3-acetamides as inhibitors of hnps-PLA(2). We describe here the extension of the structure-activity relationship to include a series of indole-3-glyoxamide derivatives. Functionalized indole-3-glyoxamides with an acidic substituent appended to the 4- or 5-position of the indole ring were prepared and tested as inhibitors of hnps-PLA(2). It was found that the indole-3-glyoxamides with a 4-oxyacetic acid substituent had optimal inhibitory activity. These inhibitors exhibited an improvement in potency over the best of the indole-3-acetamides, and LY315920 (6m) was selected for evaluation clinically as an hnps-PLA(2) inhibitor.