N-(1-methyl-1-phenylethyl)picolinamide | 1404616-63-2

• 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-(1-methyl-1-phenylethyl)picolinamide
• 英文别名: N-(2-phenylpropan-2-yl)picolinamide；N-(2-phenylpropan-2-yl)pyridine-2-carboxamide
• CAS: 1404616-63-2
• 化学式: C₁₅H₁₆N₂O
• 分子量: 240.305
• InChiKey: IZOQOYKXROVVOY-UHFFFAOYSA-N

物化性质

• 沸点：
  454.6±28.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1-methyl-1-phenylethyl)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 12.0h， 以52%的产率得到N-(2-(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-吡啶甲酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.5h， 生成 N-(1-methyl-1-phenylethyl)picolinamide
  参考文献：
  名称：

  辅助辅助、钯催化的 sp2 和 sp3 C-H 键的芳基化和烷基化的范围和限制

  摘要：

  已经研究了钯催化、辅助辅助的胺和羧酸衍生物的 sp 2和 sp 3 C-H 键的直接芳基化和烷基化的范围。该方法使用乙酸钯催化剂、底物、芳基、烷基、苄基或烯丙基卤化物和无机碱，在叔戊醇或水溶剂中，温度为 100–140 °C。芳基和烷基碘以及苄基和烯丙基溴是该转化中的有效试剂。吡啶甲酸助剂用于胺γ-官能化，8-氨基喹啉助剂用于羧酸β-官能化。为了获得最佳结果，需要对碱、添加剂和溶剂进行一些优化。

  DOI：

  10.1021/jo4013628

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。
• Copper(II) mediated C-8 amination of 1-naphthylamide derivatives with acyclic and cyclic amines
  作者：Tapan Sahoo、Souvik Sarkar、Subhash Chandra Ghosh

  DOI：10.1016/j.tetlet.2021.152858

  日期：2021.3

  A simple and facile copper(II) mediated protocol for C-8 amination of 1-naphthylamide derivatives is reported here. Picolinamide and its derivatives were used as a bidentate directing group for the C-8 amination reaction. Various substituted naphthylamide derivatives with numerous cyclic and acyclic amines proceed in good yields under mild conditions. Air was used solely as an oxidant.

  此处报道了一种简单且容易的铜（II）介导的用于1-萘酰胺衍生物的C-8胺化的方案。吡啶甲酸酰胺及其衍生物用作C-8氨基化反应的双齿指导基团。在温和条件下，具有许多环状和无环胺的各种取代的萘酰胺衍生物均以高收率进行。空气仅用作氧化剂。
• Directed Amination of Non-Acidic Arene CH Bonds by a Copper-Silver Catalytic System
  作者：Ly Dieu Tran、James Roane、Olafs Daugulis

  DOI：10.1002/anie.201300135

  日期：2013.6.3

  Amine meets arene: A method for direct amination of β‐C(sp2)H bonds of benzoic acid derivatives and γ‐C(sp2)H bonds of benzylamine derivatives has been developed. The reaction is catalyzed by Cu(OAc)2 and a Ag2CO3 cocatalyst, and shows high generality and functional‐group tolerance, as well as providing a straightforward means for the preparation of ortho‐aminobenzoic acid derivatives.

  胺遇到芳烃：已经开发了一种直接胺化苯甲酸衍生物的 β-C(sp 2 )  H 键和苄胺衍生物的γ-C(sp 2 )  H 键的方法。该反应由Cu(OAc) 2和Ag 2 CO 3助催化剂催化，具有高度的通用性和官能团耐受性，并为制备邻氨基苯甲酸衍生物提供了一种直接的方法。
• Traceless Directing Group Assisted Cobalt-Catalyzed C−H Carbonylation of Benzylamines
  作者：Fei Ling、Chongren Ai、Yaping Lv、Weihui Zhong

  DOI：10.1002/adsc.201700780

  日期：2017.11.10

  The first example of cobalt‐catalyzed C(sp2)−H carbonylation of benzylamines using a traceless directing group is reported, which was successfully applied to the synthesis of N−unprotected iso‐indolinones through direct C−H/N−H bonds activation. This protocol tolerates a variety of functional groups and provides a facile and efficient method for the formal synthesis of (+)‐garenoxacin.

  报道了使用无痕导向基团的钴催化苄胺的C（sp 2）-H羰基羰基化的第一个实例，该实例已成功地用于通过直接CH / H / NH键活化而合成N-未保护的异吲哚啉酮。该方案可耐受多种官能团，并为（+）-加仑沙星的正式合成提供了一种简便而有效的方法。
• Expedient Cobalt-Catalyzed C–H Alkynylation of (Enantiopure) Benzylamines
  作者：Vinod G. Landge、Siba P. Midya、Jagannath Rana、Dinesh R. Shinde、Ekambaram Balaraman

  DOI：10.1021/acs.orglett.6b02549

  日期：2016.10.21

  A unified strategy for cobalt-catalyzed ortho-C–H bond alkynylation of benzylamines is reported. Simple, commercially available CoBr2 was used as a cobalt source. The developed alkynylation strategy is robust and efficient and has a broad substrate scope including 1°, 2°, and 3° benzylamines. The mechanistic study shows that C–H bond cleavage is reversible, and the kinetic study illustrates that the

  据报道，钴催化苄胺的邻位-C-H键烷基化的统一策略。简单的市售CoBr 2被用作钴源。发达的炔基化策略稳定有效，具有广泛的底物范围，包括1°，2°和3°苄胺。机理研究表明，CH键的断裂是可逆的，动力学研究表明，反应速率仅取决于催化剂。