N-(4-bromobenzyl)pivalamide | 1308290-11-0

• 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-(4-bromobenzyl)pivalamide
• 英文别名: N-[(4-bromophenyl)methyl]-2,2-dimethylpropanamide
• CAS: 1308290-11-0
• 化学式: C₁₂H₁₆BrNO
• 分子量: 270.169
• InChiKey: VGFDHMWMPBKAHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-bromobenzyl)pivalamide 在 甲醇 、 dipotassium peroxodisulfate 、 palladium diacetate 、 potassium carbonate 作用下， 反应 20.0h， 生成 N-(4-bromobenzyl)-3-hydroxy-2,2-dimethylpropanamide
  参考文献：
  名称：

  Palladium-Catalyzed β-Acyloxylation of Simple Amide via sp³ C–H Activation

  摘要：

  beta-Acylcoxy amides are prepared in moderate to high yields by palladium-catalyzed acyloxylation of primary sp(3) C-H bonds from simple amides without any special directing group. A catalytic system of Pd(OAc)(2)/CF3CO2H/K2S2O8 is available to various amides with N-substituted by linear alkanes, cyclic alkanes, and electron-deficient benzyl compounds in this reaction. Acyloxylated products could be transformed easily to the corresponding beta-hydroxy amides.

  DOI：

  10.1021/ol403393w
• 作为产物：
  描述：

  对溴苄胺 、 三甲基乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-bromobenzyl)pivalamide
  参考文献：
  名称：

  Palladium-Catalyzed β-Mesylation of Simple Amide via Primary sp³ C–H Activation

  摘要：

  A beta-mesylation of primary sp(3) C-H bonds from simple amides with methanesulfonic anhydride; (Ms2O) has been established successfully A 80 degrees C in a Pd(OAc)(2) (catalyst)/K2S2O8 (oxidant)CF3CH2OH (solvent) system. These amide substrates involve N-monosubstituted linear,, branch, or cyclic alkanes, and electron-deficient benzyl compounds. The beta-mesylated amide products can be converted easily to beta-fluoroamideS or beta-lactams through inter- or intramolecular S(N)2 processes.

  DOI：

  10.1021/acs.orglett.7b00536

文献信息

• Palladium-Catalyzed β-Arylation of Amide via Primary sp³C–H Activation
  作者：Ren Zhao、Wenjun Lu

  DOI：10.1021/acs.organomet.8b00325

  日期：2018.7.9

  A beta-arylation of primary sp(3)C-H bonds on simple amides such as pivalamides with aryl iodides/ CF3CO2Ag has been established successfully at 120 degrees C in a Pd(OAc)(2) (catalyst)/CF3CH2OH (solvent) system. Pivalamides including (BuCONH2)-Bu-t, (BuCONHR)-Bu-t, and (BuCONR2)-Bu-t undergo the arylations smoothly to afford beta-aryl pivalamides in moderate to good yields. Various aryl iodides are available bearing either electron-donating or electron-withdrawing substituted groups in the coupling reactions.