N,N-dibenzylpicolinamide

• 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,N-dibenzylpicolinamide
• 英文别名: N,N-dibenzyl-2-pyridylamide；N,N-dibenzylpyridine-2-carboxamide
• 化学式: C₂₀H₁₈N₂O
• 分子量: 302.376
• InChiKey: OFSIFPKVGDAWIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-dibenzylpicolinamide 在 dicobalt octacarbonyl 、 sodium hydroxide 作用下， 以 甲苯 、 甲醇 、 水 为溶剂， 反应 4.0h， 以60%的产率得到N,N-dibenzyl-1-(pyridin-2-yl)methanamine
  参考文献：
  名称：

  羰基钴基甲酰胺氢化硅烷化催化剂

  摘要：

  AbstractThe cobalt carbonyl [Co2(CO)8] complex is employed as a useful catalyst for the reduction of tertiary amides to the corresponding tertiary amines using 1,1,3,3‐tetramethyldisiloxane (TMDS) and poly(methylhydrosiloxane) (PMHS) as silane reagents under thermal (100 °C) or photo‐assisted conditions (UV, 350 nm at room temperature). Of particular interest, a low catalytic amount (0.5 mol%) of [Co2(CO)8] is used to perform the reaction with 2.2 equiv. of PMHS at 100 °C for 3 h. This reaction is the first example of a cobalt‐catalyzed hydrosilylation of amides.magnified image

  DOI：

  10.1002/adsc.201300664
• 作为产物：
  描述：

  2-吡啶甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N,N-dibenzylpicolinamide
  参考文献：
  名称：

  铑（III）催化的Picolinamides的氧化烯烃氧化反应：3-Alkenylpicolinamides的便捷合成

  摘要：

  已开发了铑（III）催化的吡啶甲酰胺衍生物的选择性烯烃化反应。该反应显示出高区域选择性，低催化剂负载量（0.5 mol％），高收率和良好的官能团耐受性，为合成3-链烯基吡啶甲酸酰胺提供了便利的策略。

  DOI：

  10.1002/adsc.201300895

文献信息

• A comparative study of amide-bond forming reagents in aqueous media – Substrate scope and reagent compatibility
  作者：Matthew Badland、Robert Crook、Bastien Delayre、Steven J. Fussell、Iain Gladwell、Michael Hawksworth、Roger M. Howard、Robert Walton、Gerald A. Weisenburger

  DOI：10.1016/j.tetlet.2017.10.014

  日期：2017.11

  A survey of amidation reagents demonstrating DIC-HOPO, DMT-MM, COMU-collidine, TPTU-NMI, EEDQ, CDI and EDC-Oxyma to be effective for the coupling of carboxylic acids with amines in the presence of water and the absence of problematic dipolar aprotic solvents is reported. DMT-MM was shown to provide the best yields for the coupling of a secondary amine, TPTU-NMI and COMU-collidine for aniline, whilst

  酰胺化试剂的研究表明DIC-HOPO，DMT-MM，COMU-可力丁，TPTU-NMI，EEDQ，CDI和EDC-氧合酶可有效地在有水和无问题的情况下将羧酸与胺偶联据报道偶极非质子溶剂。已证明DMT-MM为偶联仲胺，TPTU-NMI和COMU-可力丁提供苯胺的收率最高，而DIC与HOPO的结合提供了最广泛的底物范围，对于空间要求苛刻的羧酸提供了最高收率。
• Efficient Synthesis of Isoquinolines via Rh(III)-Catalyzed Oxidative Annu­lation of Picolinamides with Alkynes
  作者：Bing-Feng Shi、Zhen-Chao Qian、Jun Zhou、Bo Li

  DOI：10.1055/s-0033-1340870

  日期：——

  An efficient synthesis of isoquinolines via Rh(III)-catalyzed oxidative annulation of picolinamides with alkynes using Cu(OAc)(2) as an oxidant has been developed. The scope of the reaction was studied with a selection of various picolinamides and alkynes, and the desired isoquinolines were obtained in good to excellent yields.
• 8-AMINO- 1,2,4]TRIAZOLO 1,5-A]PYRIDINE-6-CARBOXYLIC ACID AMIDE
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1435952A1

  公开（公告）日：2004-07-14
• [EN] 8-AMINO-[1,2,4]TRIAZOLO[1,5-A]PYRIDINE-6-CARBOXYLIC ACID AMIDE<br/>[FR] AMIDE D'ACIDE 8-AMINO-[1,2,4]TRIAZOLO[1,5-A]PYRIDINE-6-CARBOXYLIQUE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2003030904A1

  公开（公告）日：2003-04-17

  The invention relates to compounds of formula (I), wherein R1 is -NR'R', wherein R' and R' are independently from each other lower alkyl, -(CH¿2?)n-C(O)NR?aRb¿, -(CH¿2?)n-heteroaryl, -(CH2)n-aryl, -(CH2)n-CN, -(CH2)n-O-lower alkyl or -(CH2)n-cycloalkyl, or R'and R' form together with the N-atom a five or six-membered none aromatic ring, which may contain one additional O or S heteroatom, and whose rings may be unsubstituted or substituted by one or two substituents, selected from the group consisting of lower alkyl, -C(O)NR?aRb¿ or -(CH¿2?)n-O-lower alkyl and R?aRb¿ are independently from each other hydrogen or lower alkyl; R2 is aryl or heteroaryl, unsubstituted or substituted ba lower alkyl or halogen; n is 0, 1, 2 or 3; and to their pharmaceutically acceptable salts. The compounds may be used in the treatment of diseases, associated with the adenosime A2 receptor.
• Rhodium(III)-Catalyzed Oxidative Olefination of Picolinamides: Convenient Synthesis of 3-Alkenylpicolinamides
  作者：Jun Zhou、Bo Li、Zhen-Chao Qian、Bing-Feng Shi

  DOI：10.1002/adsc.201300895

  日期：2014.3.24

  A rhodium(III)‐catalyzed selective olefination of picolinamide derivatives has been developed. The reaction shows high regioselectivity, low catalyst loading (0.5 mol%), high yield and good functional group tolerance, providing a convenient strategy for the synthesis of 3‐alkenylpicolinamides.

  已开发了铑（III）催化的吡啶甲酰胺衍生物的选择性烯烃化反应。该反应显示出高区域选择性，低催化剂负载量（0.5 mol％），高收率和良好的官能团耐受性，为合成3-链烯基吡啶甲酸酰胺提供了便利的策略。