N,N-diethyl-3-oxo-4-phenylbutanamide | 135878-37-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N,N-diethyl-3-oxo-4-phenylbutanamide
• CAS: 135878-37-4
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: XFBBMNSJBWHAJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-3-oxo-4-phenylbutanamide 、 p-nitrobenzenesulfonyl peroxide 在 zinc(II) chloride 作用下， 以 乙酸乙酯 为溶剂， 以59%的产率得到N,N-diethyl-2-((p-nitrobenzenesulfonyl)oxy)-3-oxo-4-phenylbutanamide
  参考文献：
  名称：

  A simple synthesis of 2,3-diketo amides from 3-keto amides

  摘要：

  The conversion of 3-keto amides to 2-(nosyloxy)-3-keto amides 4a-g followed by DBU-promoted, reductive elimination of p-nitrobenzenesulfinic acid provides a short, simple method for the preparation of 2,3-dioxo amides (tricarbonyl amides) 5a-f in high yields.

  DOI：

  10.1021/jo00022a040
• 作为产物：
  描述：

  N,N-二乙基乙酰胺 、 苯乙酸甲酯 在 正丁基锂 、 二异丙胺 作用下， 以72%的产率得到N,N-diethyl-3-oxo-4-phenylbutanamide
  参考文献：
  名称：

  A simple synthesis of 2,3-diketo amides from 3-keto amides

  摘要：

  The conversion of 3-keto amides to 2-(nosyloxy)-3-keto amides 4a-g followed by DBU-promoted, reductive elimination of p-nitrobenzenesulfinic acid provides a short, simple method for the preparation of 2,3-dioxo amides (tricarbonyl amides) 5a-f in high yields.

  DOI：

  10.1021/jo00022a040

文献信息

• Chiral Phosphinyl Enamines and Their Asymmetric Reduction through Group-Assisted Purification Chemistry Leading to Enantiopure β-Amino Esters/Amides
  作者：Bo Jiang、Guigen Li、Shuo Qiao、Jianbin Wu、Junming Mo、Preston Spigener、Brian Zhao

  DOI：10.1055/s-0036-1589080

  日期：2017.11

  of new chiral N -phosphinyl β-enamino esters and amides were successfully prepared with excellent Z -stereoselectivity ( Z / E > 99:1 in nearly all cases). Group-assisted purification chemistry proved to be an efficient method for the asymmetric reduction of the resulting β-enamino esters/amides to give enantiopure β-amino esters/amides. The asymmetric reduction can be controlled efficiently by using

  以优异的Z-立体选择性（几乎所有情况下Z/E>99:1）成功制备了一系列新型手性N-膦酰基β-烯氨基酯和酰胺。组辅助纯化化学被证明是不对称还原所得 β-烯氨基酯/酰胺以得到对映体纯 β-氨基酯/酰胺的有效方法。通过使用氰基硼氢化钠和乙酸的组合可以有效地控制不对称还原。
• A Palladium-Catalyzed Carbonylative-Deacetylative Sequence to 1,3-Keto Amides
  作者：Dennis U. Nielsen、Signe Korsager、Anders T. Lindhardt、Troels Skrydstrup

  DOI：10.1002/adsc.201400545

  日期：2014.11.24

  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