N-(2-(4-tert-butylphenyl)propan-2-yl)picolinamide | 1443144-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(2-(4-tert-butylphenyl)propan-2-yl)picolinamide
• 英文别名: N-{2-(4-tert-butylphenyl)-2-propyl}picolinamide
• CAS: 1443144-13-5
• 化学式: C₁₉H₂₄N₂O
• 分子量: 296.412
• InChiKey: OHZXIJCLVYWZMY-UHFFFAOYSA-N

物化性质

• 沸点：
  482.3±33.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  41.99
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(2-(4-tert-butylphenyl)propan-2-yl)picolinamide 在 N,N-二甲基丙烯基脲 、 copper(l) iodide 、 silver fluoride 、 N-甲基吗啉氧化物 作用下， 反应 4.0h， 以43%的产率得到N-(2-(4-tert-butyl-2,6-difluorophenyl)propan-2-yl)picolinamide
  参考文献：
  名称：

  Copper-Catalyzed, Directing Group-Assisted Fluorination of Arene and Heteroarene C–H Bonds

  摘要：

  We have developed a method for direct, copper-catalyzed, auxiliary-assisted fluorination of beta-sp(2) C-H bonds of benzoic acid derivatives and gamma-sp(2) C-H bonds of alpha,alpha-disubstituted benzylamine derivatives. The reaction employs a CuI catalyst, a AgF fluoride source, and DMF, pyridine, or DMPU solvent at moderately elevated temperatures. Selective mono- or difluorination can be achieved by simply changing reaction conditions. The method shows excellent functional group tolerance and provides a straightforward way for the preparation of ortho-fluorinated benzoic acids.

  DOI：

  10.1021/ja4047125
• 作为产物：
  描述：

  2-(4-tert-butylphenyl)propan-2-amine 、 picolinic acid 以 二氯甲烷 为溶剂， 反应 4.0h， 以754 mg的产率得到N-(2-(4-tert-butylphenyl)propan-2-yl)picolinamide
  参考文献：
  名称：

  Copper-Catalyzed, Directing Group-Assisted Fluorination of Arene and Heteroarene C–H Bonds

  摘要：

  We have developed a method for direct, copper-catalyzed, auxiliary-assisted fluorination of beta-sp(2) C-H bonds of benzoic acid derivatives and gamma-sp(2) C-H bonds of alpha,alpha-disubstituted benzylamine derivatives. The reaction employs a CuI catalyst, a AgF fluoride source, and DMF, pyridine, or DMPU solvent at moderately elevated temperatures. Selective mono- or difluorination can be achieved by simply changing reaction conditions. The method shows excellent functional group tolerance and provides a straightforward way for the preparation of ortho-fluorinated benzoic acids.

  DOI：

  10.1021/ja4047125

文献信息

• Chelate-Assisted Direct Selenation of Aryl C–H Bonds with Diselenides Catalyzed by Palladium
  作者：Masayuki Iwasaki、Yuta Tsuchiya、Kiyohiko Nakajima、Yasushi Nishihara

  DOI：10.1021/ol502439m

  日期：2014.9.19

  A direct selenation of inert C–H bonds of benzamide derivatives and their related compounds with diselenides has been achieved with the palladium catalyst. The reaction was compatible with a variety of functional groups, including a bromo group. Primitive mechanistic insights revealed that the reaction proceeded through a C–H bond cleavage and the sequential oxidative addition of diselenides. The present

  钯催化剂已经实现了苯甲酰胺衍生物及其相关化合物的惰性C–H键与二硒化物的直接硒化。该反应与包括溴基在内的多种官能团相容。原始的机械学见解表明，该反应通过C–H键断裂和二硒化物的顺序氧化加成进行。本发明的合成方法可以应用于容易被认为是有希望的杂环材料的亚硒酮的合成。