N-formylbutyramide

• 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-formylbutyramide
• 英文别名: Buttersaeure->；Butyrylformamid；N-formylbutanamide
• 化学式: C₅H₉NO₂
• mdl: MFCD19219608
• 分子量: 115.132
• InChiKey: YMFONJSGPAJQCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-formylbutyramide 、 (E)-3-methoxycarbonyl-2-propenylidenetriphenylphosphorane 以 二氯甲烷 为溶剂， 以42%的产率得到(2E,4Z)-methyl 5-butyramidopenta-2,4-dienoate
  参考文献：
  名称：

  Fast and efficient one step synthesis of dienamides

  摘要：

  报告了一种快速高效的一步合成二烯酰胺的方法。该简明的方法依赖于酰亚胺作为反应中间体，并允许优先形成Z,E-二烯酰胺，产率良好。

  DOI：

  10.1039/b901797f
• 作为产物：
  描述：

  丁酰胺 、 1H-苯并三唑-1-甲醛 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以34%的产率得到N-formylbutyramide
  参考文献：
  名称：

  Fast and efficient one step synthesis of dienamides

  摘要：

  报告了一种快速高效的一步合成二烯酰胺的方法。该简明的方法依赖于酰亚胺作为反应中间体，并允许优先形成Z,E-二烯酰胺，产率良好。

  DOI：

  10.1039/b901797f

文献信息

• n‐Bu4NI/K2S2O8 Mediated Csp2−Csp2 Bond Cleavage – Transformylation from p‐Anisaldehyde to Primary Amides
  作者：Xiaochen Liu、Samual Hee、Netanel G. Sapir、Alvin Li、Jianbo Liu、Yu Chen

  DOI：10.1002/adsc.202301505

  日期：2024.6.10

  amides is reported. The mechanistic studies suggest the reaction occurs via a single electron transfer pathway. Based on the DFT electronic structure calculations of various reaction pathways, the most plausible mechanism involves the formation of a phenyl radical cation and an arenium ion as the key intermediates. It represents the first example that p‐anisaldehyde is employed as a formyl source via

  据报道，n-Bu4NI/K2S2O8 介导的从对茴香醛到伯酰胺的转化。机理研究表明该反应通过单一电子转移途径发生。基于各种反应途径的 DFT 电子结构计算，最合理的机制涉及形成苯基自由基阳离子和芳烃离子作为关键中间体。它代表了对茴香醛通过非金属介导的 Csp2-Csp2 键断裂用作甲酰源的第一个例子。
• Protecting Group Free, Stereocontrolled Synthesis of β-Halo-enamides
  作者：Adele E. Pasqua、James J. Crawford、De-Liang Long、Rodolfo Marquez

  DOI：10.1021/jo202130e

  日期：2012.3.2

  Enamides, dienamides, and enynamides are important building blocks in synthetic, biological, and medicinal chemistry as well as materials science. Despite the extensive breath of their potential utility in synthetic chemistry, there is a lack of simple, high-yielding methods to deliver them efficiently and as single isomers. In this paper, we present a novel, protecting group free, efficient, and stereoselective approach to the generation of beta-halo-enamides. The methodology presented provides a robust synthetic platform from which E- or Z-enamides can be generated in good yields and with complete stereocontrol.
• Regioselective synthesis of β-iodo-enamides and β-yn-enamides
  作者：Adele E. Pasqua、Lynne H. Thomas、James J. Crawford、Rodolfo Marquez

  DOI：10.1016/j.tet.2011.07.033

  日期：2011.9

  Iodo-enamides were synthesised in a single step, in good yield and with complete selectivity from N-formyl imides. The beta-iodo-enamides are stable and were converted efficiently into novel geometrically defined beta-yn-enamides. (C) 2011 Elsevier Ltd. All rights reserved.