2-bromo-N-(2-iodophenyl)-N-methylpropanamide | 1239573-77-3

• 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: 2-bromo-N-(2-iodophenyl)-N-methylpropanamide
• CAS: 1239573-77-3
• 化学式: C₁₀H₁₁BrINO
• 分子量: 368.012
• InChiKey: RKCOKXIGILSBMF-UHFFFAOYSA-N

物化性质

• 沸点：
  377.4±27.0 °C(Predicted)
• 密度：
  1.904±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(2-iodophenyl)-N-methylpropanamide 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 、 对甲苯磺酰胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.25h， 以72%的产率得到1,3-二甲基-2-喹噁啉酮
  参考文献：
  名称：

  Copper-Catalyzed Cascade Syntheses of 2H-benzo[b][1,4]thiazin-3(4H)-ones and Quinoxalin-2(1H)-ones through Capturing S and N Atom Respectively from AcSH and TsNH₂

  摘要：

  A copper-catalyzed cascade method has been developed to synthesize the 2H-benzo[b][1,4]thiazin-3(4H)-ones from 2-halo-N-(2-halophenyl)-acetamides 1 and AcSH via the S(N)2/deacetylation/coupling process, and to synthesize the quinoxalin-2(1H)-ones from 1 and TsNH2 via the S(N)2/coupling/desulfonation process. The target products were obtained with diversity at three positions on their scaffolds.

  DOI：

  10.1021/jo101253a
• 作为产物：
  描述：

  N-methyl-2-iodoaniline 、 2-溴丙酰溴 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到2-bromo-N-(2-iodophenyl)-N-methylpropanamide
  参考文献：
  名称：

  Domino Carbopalladation–Cross-Coupling for the Synthesis of 3,3-Disubstituted Oxindoles

  摘要：

  This study examines a domino carbopalladation-cross-coupling reaction for the formation of valuable oxindole scaffolds. Furthermore, the reaction sequence forges vicinal stereocenters In a stereospecific manner through the formation of two carbon carbon bonds and, thereby, rapidly generates complexity. The reaction gives high yields for a variety of acrylamide substrates, and various organoboranes have also been evaluated for the cross-coupling. This work offers insight into the relative rates determining a successful carbopalladation-cross-coupling reaction and how to favor the desired reaction pathway.

  DOI：

  10.1021/ol301539p

文献信息

• Iminyl Radicals from α-Azido <i>o</i>-Iodoanilides via 1,5-H Transfer Reactions of Aryl Radicals: New Transformation of α-Azido Acids to Decarboxylated Nitriles
  作者：Giorgio Bencivenni、Tommaso Lanza、Rino Leardini、Matteo Minozzi、Daniele Nanni、Piero Spagnolo、Giuseppe Zanardi

  DOI：10.1021/jo800453z

  日期：2008.6.1

  The radical reaction of tributyltin hydride with o-iodo-N-methylanilides derived from alpha-azido acids provides an excellent access to alpha-(aminocarbonyl)iminyl radicals through 1,5-hydrogen transfer reaction of initially formed aryl radicals followed by beta-elimination of dinitrogen from ensuing alpha-azido-alpha-(aminocarbonyl)alkyl radicals. The outcoming iminyls display a peculiar tendency to form corresponding nitriles by beta-elimination of aminocarbonyl radicals.