(S)-N-allyl-2-bromo-N-(1-phenyl-ethyl)acetamide | 811449-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-allyl-2-bromo-N-(1-phenyl-ethyl)acetamide
• 英文别名: (s)-N-allyl-2-bromo-N-(1-phenylethyl)acetamide；2-bromo-N-[(1S)-1-phenylethyl]-N-prop-2-enylacetamide
• CAS: 811449-04-4
• 化学式: C₁₃H₁₆BrNO
• 分子量: 282.18
• InChiKey: NDALUDCHGBCTHR-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-N-allyl-2-bromo-N-(1-phenyl-ethyl)acetamide 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 丙酮 、 苯 为溶剂， 反应 2.5h， 生成 (4S)-4-甲基吡咯烷酮-2-酮
  参考文献：
  名称：

  The 5-exo-trig radical cyclization reaction under reductive and oxidative conditions in the synthesis of optically pure GABA derivatives

  摘要：

  Free radical precursors 4a and 4b were synthesized and treated under reductive or oxidative conditions to obtain the corresponding optically pure pyrrolidinones 5-8, which were subsequently transformed into corresponding optically pure GABA derivatives 9-11. When reductive radical conditions (4a-->7 and 8) were used, a Ph1-5 migration product 14 was obtained; presumably depending upon the specific conformation of the rotamer precursor and also 14 was found to be a kinetic product. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.053
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 在 4-二甲氨基吡啶 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.0h， 生成 (S)-N-allyl-2-bromo-N-(1-phenyl-ethyl)acetamide
  参考文献：
  名称：

  The 5-exo-trig radical cyclization reaction under reductive and oxidative conditions in the synthesis of optically pure GABA derivatives

  摘要：

  Free radical precursors 4a and 4b were synthesized and treated under reductive or oxidative conditions to obtain the corresponding optically pure pyrrolidinones 5-8, which were subsequently transformed into corresponding optically pure GABA derivatives 9-11. When reductive radical conditions (4a-->7 and 8) were used, a Ph1-5 migration product 14 was obtained; presumably depending upon the specific conformation of the rotamer precursor and also 14 was found to be a kinetic product. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.053

文献信息

• Stereoselective 5-exo-trig radical cyclization in the enantioselective synthesis of Pregabalin
  作者：Verónica Rodríguez、Leticia Quintero、Fernando Sartillo-Piscil

  DOI：10.1016/j.tetlet.2007.04.054

  日期：2007.6

  A practical stereoselective 5-exo-trig radical cyclization procedure was developed in order to prepare enantiomerically pure GABA derivative precursors (4-alkyl-pyrrolidin-2-ones). This procedure allows much more rapid access to optically pure GABA derivatives, such as the powerful antiepileptic agent (S)-(+)-3-aminomethyl-5-methylhexanoic acid (Pregabaline).

  为了制备对映体纯的GABA衍生物前体（4-烷基-吡咯烷烃-2-酮），开发了一种实用的立体选择性5- exo - trig自由基环化方法。该程序允许更快速地获得光学纯的GABA衍生物，例如强大的抗癫痫药（S）-（+）-3-氨基甲基-5-甲基己酸（PreGABAline）。
• A novel stereoselective tin-free radical protocol for the enantioselective synthesis of pyrrolidinones and its application to the synthesis of biologically active GABA-derivatives
  作者：Verónica Rodríguez-Soria、Leticia Quintero、Fernando Sartillo-Piscil

  DOI：10.1016/j.tet.2008.01.063

  日期：2008.3

  fashion, via a sequential 5-exo-trig radical cyclization-hydrogen or bromine atom-transfer process, under non-tin conditions. Interestingly, when N-allyl-α-bromoacetamides were treated with triethylborane/MeOH(excess)/BF3·OEt2 in toluene at −78 °C, a tandem 5-exo-trig radical cyclization-hydrogen atom-transfer reaction operated, on the other hand, a tandem 5-exo-trig radical cyclization-bromine atom-transfer

  光学纯的4-烷基吡咯啉-2-酮是从手性合成Ñ在高选择性和立体控制的方式-烯丙基-α-bromoacetamides，通过顺序5-外型- trig的自由基环化氢或溴原子的转移过程中，在非锡条件下。有趣的是，当N-烯丙基-α-溴乙酰胺在-78°C下用甲苯中的三乙基硼烷/ MeOH（过量）/ BF 3 ·OEt 2处理时，进行串联的5- exo - trig自由基环化-氢原子转移反应，另一方面，串联5- exo - trig当在-78°C下用等摩尔量的MeOH的THF溶液进行自由基环化-溴原子转移反应时，收率和立体选择性高。因此，通过该锡自由基途径合成了光学纯的4-烷基-吡咯啉-2-酮，并将其转化为它们相应的具有生物活性的GABA衍生物普瑞巴林和CAMP。