4-[(2-bromophenyl)amino]cyclohexanone ethylene acetal | 501346-93-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-[(2-bromophenyl)amino]cyclohexanone ethylene acetal
• 英文别名: N-(2-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-amine
• CAS: 501346-93-6
• 化学式: C₁₄H₁₈BrNO₂
• mdl: MFCD11144858
• 分子量: 312.206
• InChiKey: YRHJQVPZILWLDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(2-bromophenyl)amino]cyclohexanone ethylene acetal 在 盐酸 、 potassium phosphate 、 四(三苯基膦)钯 、 potassium carbonate 、 lithium iodide 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 96.0h， 生成 1-benzyl-2,3,4,6-tetrahydro-2,6-methano-1H-1-benzazocin-5-one
  参考文献：
  名称：

  Intramolecular Pd-Mediated Processes of Amino-Tethered Aryl Halides and Ketones:  Insight into the Ketone α-Arylation and Carbonyl-Addition Dichotomy. A New Class of Four-Membered Azapalladacycles

  摘要：

  An exploration of the scope and limitations of Pd(0)-catalyzed intramolecular coupling reactions of amino-tethered aryl halides and ketones has been conducted. Two different and competitive reaction pathways starting from omega-(2-haloanilino) alkanones, enolate arylation and addition to the carbonyl group, have been observed, while (omega-(2-halobenzylamino) alkanones exclusively underwent the enolate arylation process. The dichotomy between ketone alpha-arylation and carbonyl-addition in the reactions of omega-(2-haloanilino) alkanones has been rationalized by the intermediacy of unprecedented four-membered azapalladacycles, from which X-ray data and chemical behavior are reported.

  DOI：

  10.1021/ja029114w
• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 、 2-溴苯胺 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.17h， 以56%的产率得到4-[(2-bromophenyl)amino]cyclohexanone ethylene acetal
  参考文献：
  名称：

  酮与苯胺的快速微波辅助还原胺化

  摘要：

  使用微波技术，开发了一种新方案，可提高酮与苯胺直接还原胺化的反应速率和整体效率。当使用三乙酰氧基硼氢化钠作为还原剂时，各种电子不同的苯胺都可以实现高产率和更高的反应速率。此外，我们发现该协议也可以应用于醛类。

  DOI：

  10.1055/s-2006-949639

文献信息

• Intramolecular Pd-Mediated Processes of Amino-Tethered Aryl Halides and Ketones:  Insight into the Ketone α-Arylation and Carbonyl-Addition Dichotomy. A New Class of Four-Membered Azapalladacycles
  作者：Daniel Solé、Lluís Vallverdú、Xavier Solans、Mercè Font-Bardía、Josep Bonjoch

  DOI：10.1021/ja029114w

  日期：2003.2.1

  An exploration of the scope and limitations of Pd(0)-catalyzed intramolecular coupling reactions of amino-tethered aryl halides and ketones has been conducted. Two different and competitive reaction pathways starting from omega-(2-haloanilino) alkanones, enolate arylation and addition to the carbonyl group, have been observed, while (omega-(2-halobenzylamino) alkanones exclusively underwent the enolate arylation process. The dichotomy between ketone alpha-arylation and carbonyl-addition in the reactions of omega-(2-haloanilino) alkanones has been rationalized by the intermediacy of unprecedented four-membered azapalladacycles, from which X-ray data and chemical behavior are reported.
• Rapid Microwave-Assisted Reductive Amination of Ketones with Anilines
  作者：Barry Potter、Helen Bailey、Wesley Heaton、Nigel Vicker

  DOI：10.1055/s-2006-949639

  日期：2006.9

  Using microwave technology, a new protocol has been developed that improves the reaction rate and overall efficiency of the direct reductive amination of ketones with anilines. When using sodium triacetoxyborohydride as the reducing agent, high product yields and increased reaction rates are achieved for a variety of electronically different anilines. Furthermore, we have found that this protocol can

  使用微波技术，开发了一种新方案，可提高酮与苯胺直接还原胺化的反应速率和整体效率。当使用三乙酰氧基硼氢化钠作为还原剂时，各种电子不同的苯胺都可以实现高产率和更高的反应速率。此外，我们发现该协议也可以应用于醛类。