N,N-diethyl-3-(6-methoxynaphthalen-2-yl)-3-oxopropanamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-diethyl-3-(6-methoxynaphthalen-2-yl)-3-oxopropanamide
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: KNTWHXHJUVDIEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  一氧化碳 、 2-溴-6-甲氧基萘 、 N,N-二乙基乙酰乙酰胺 在 dichloro(cycloocta-1,5-diene)palladium (II) 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 magnesium chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以96%的产率得到N,N-diethyl-3-(6-methoxynaphthalen-2-yl)-3-oxopropanamide
  参考文献：
  名称：

  钯催化的1，3-酮酰胺的羰基化-脱乙酰化序列

  摘要：

  AbstractAn efficient three‐component reaction involving carbon monoxide with a range of aryl bromides and N‐substituted acetoacetamides is reported for the synthesis of β‐keto amides. This transformation is promoted by Pd‐catalysis followed by an acid‐mediated deacetylation upon work‐up, enabling a large number of β‐keto amides to be isolated. Finally, d2‐13C‐dyclonine could be synthesized in three steps utilizing the developed catalytic system as the key step.magnified image

  DOI：

  10.1002/adsc.201400545

文献信息

• COtab: Expedient and Safe Setup for Pd-Catalyzed Carbonylation Chemistry
  作者：Hugo P. Collin、Wallace J. Reis、Dennis U. Nielsen、Anders T. Lindhardt、Marcelo S. Valle、Rossimiriam P. Freitas、Troels Skrydstrup

  DOI：10.1021/acs.orglett.9b01423

  日期：2019.8.2

  Bench-stable tablets (COtabs) have been developed for the rapid and safe production of carbon monoxide. The tablets can be made in less than 5 min without the use of a glovebox and only require a stock solution of an amine base to liberate a specific quantity of CO in a two-chamber system. The COtabs were tested in five different carbonylation reactions and provided similar yields compared to literature procedures. Finally, a gram-scale reaction was conducted, as well as C-13-isotope labeling of the anticancer drug, olaparib.