N-(2-bromoallyl)-N-phenylacetamide | 1448025-37-3

• 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: N-(2-bromoallyl)-N-phenylacetamide
• 英文别名: N-(2-bromoprop-2-enyl)-N-phenylacetamide
• CAS: 1448025-37-3
• 化学式: C₁₁H₁₂BrNO
• 分子量: 254.126
• InChiKey: OHUKZVFLZFMOHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  N-(2-bromoallyl)-N-phenylacetamide 在 calcium hypobromite 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以91%的产率得到N-(3-bromo-2-oxopropyl)-N-phenylacetamide
  参考文献：
  名称：

  Chemoselective oxidative hydrolysis of EWG protected α-arylamino vinyl bromides to α-arylamino-α′-bromoacetones

  摘要：

  Vinyl bromides bearing an arylamino group in the vicinal position are chemoselectively transformed into interesting alpha-arylamino-alpha'-bromoacetones through a straightforward oxidative hydrolysis promoted by calcium hypobromite under mild acidic conditions. Significantly, this particular combination [vinyl bromides and Ca(BrO)(2)] avoids bromination at both the aromatic ring and activated positions in groups substituting the amine nitrogen. The usefulness of this class of brominated ketones has been shown in a Wittig homologation. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.118
• 作为产物：
  描述：

  苯胺 在 calcium oxide 作用下， 以 2-甲基四氢呋喃 、 乙腈 为溶剂， 反应 3.08h， 生成 N-(2-bromoallyl)-N-phenylacetamide
  参考文献：
  名称：

  Chemoselective oxidative hydrolysis of EWG protected α-arylamino vinyl bromides to α-arylamino-α′-bromoacetones

  摘要：

  Vinyl bromides bearing an arylamino group in the vicinal position are chemoselectively transformed into interesting alpha-arylamino-alpha'-bromoacetones through a straightforward oxidative hydrolysis promoted by calcium hypobromite under mild acidic conditions. Significantly, this particular combination [vinyl bromides and Ca(BrO)(2)] avoids bromination at both the aromatic ring and activated positions in groups substituting the amine nitrogen. The usefulness of this class of brominated ketones has been shown in a Wittig homologation. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.118

文献信息

• Benzylarylation of <i>N</i>-Allyl Anilines: Synthesis of Benzylated Indolines
  作者：Wenzhong Huang、Xiulan Li、Xuemei Song、Qing Luo、Yanping Li、Ying Dong、Deqiang Liang、Baoling Wang

  DOI：10.1021/acs.joc.9b00237

  日期：2019.5.17

  functionalization of methyl arenes across unactivated alkenes is presented. In the presence of MnCl2·4H2O and di-tert-butyl peroxide, N-allyl anilines underwent benzylation/cyclization cascade to give benzylated indolines, which are a previously unmet synthetic goal. This protocol features simple operation, broad substrate scope, and great exo selectivity.

  提出了前所未有的未活化烯烃上甲基芳烃的苄基C–H官能化。在MnCl 2 ·4H 2 O和二叔丁基过氧化物的存在下，N-烯丙基苯胺进行苄基化/环化级联反应生成苄基化的二氢吲哚，这是以前无法实现的合成目标。这个协议提供操作简单，广泛的底物范围和大外型选择性。
• Synthesis of N-Heterocycles by Dehydrogenative Annulation of N-Allyl Amides with 1,3-Dicarbonyl Compounds
  作者：Zheng-Jian Wu、Shi-Rui Li、Hai-Chao Xu

  DOI：10.1002/anie.201807683

  日期：2018.10.22

  construct cyclic structures. Reported herein is an unprecedented synthesis of pyrrolidine and tetrahydropyridine derivatives through electrochemical dehydrogenative annulation of N‐allyl amides with 1,3‐dicarbonyl compounds. The electrolytic method employs an organic redox catalyst, which obviates the need for oxidizing reagents and transition‐metal catalysts. In these reactions, the N‐allyl amides serve

  在无氧化剂的条件下进行脱氢环化是构建环状结构的理想策略。本文报道了N-烯丙基酰胺与1,3-二羰基化合物的电化学脱氢环化反应，合成了吡咯烷和四氢吡啶衍生物。电解方法使用有机氧化还原催化剂，因此无需使用氧化剂和过渡金属催化剂。在这些反应中，N-烯丙基酰胺可作为四原子供体，与丙二酸二甲酯反应，经（4 + 1）环化反应生成吡咯烷，或与β-酮酸酯反应，经（4 + 2）环化反应生成四氢吡啶衍生物。 。
• Chemoselective oxidative hydrolysis of EWG protected α-arylamino vinyl bromides to α-arylamino-α′-bromoacetones
  作者：Vittorio Pace、Laura Castoldi、María J. Hernáiz、Andrés R. Alcántara、Wolfgang Holzer

  DOI：10.1016/j.tetlet.2013.05.118

  日期：2013.8

  Vinyl bromides bearing an arylamino group in the vicinal position are chemoselectively transformed into interesting alpha-arylamino-alpha'-bromoacetones through a straightforward oxidative hydrolysis promoted by calcium hypobromite under mild acidic conditions. Significantly, this particular combination [vinyl bromides and Ca(BrO)(2)] avoids bromination at both the aromatic ring and activated positions in groups substituting the amine nitrogen. The usefulness of this class of brominated ketones has been shown in a Wittig homologation. (c) 2013 Elsevier Ltd. All rights reserved.