N-butylpent-4-enamide | 107515-69-5

• 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-butylpent-4-enamide
• 英文别名: N-Butyl-4-pentenamide
• CAS: 107515-69-5
• 化学式: C₉H₁₇NO
• mdl: MFCD24392379
• 分子量: 155.24
• InChiKey: GGMXKJPSVLVMHG-UHFFFAOYSA-N

物化性质

• 沸点：
  277.6±19.0 °C(Predicted)
• 密度：
  0.871±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-butylpent-4-enamide 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 13.0h， 生成 N-butyl-N-pent-4-enoylcarbamoyl chloride
  参考文献：
  名称：

  Multiple Reaction Channels of (N-Acyl-N-alkylcarbamoyl)oxyl Radicals from N-Acyl PTOC Carbamates

  摘要：

  N-Acyl-N-alkyl-N'-hydroxypyridine-2-thione carbamates (N-acyl PTOC carbamates) 1 are prepared in good to excellent yield by reactions of N-acylcarbamoyl chlorides with N-hydroxypyridine-2-thione sodium salt. Methods for production of the requisite carbamoyl chlorides by reaction of a secondary amide with trimethylsilyl triflate followed by treatment with phosgene were optimized. Precursors 1 react in radical chain reactions to give the title radicals (2) that can further react by several pathways. Decarboxylations of radicals 2 give amidyl radicals, and this method is excellent for production of acetamidyl radicals and in particular the N-methylacetarnidyl radical which is difficult to prepare by other routes. 5-Exo cyclizations of amidyl radicals produced by decarboxylation of 2 give, ultimately, lactams and N-acylpyrrolidines. 1,5-Hydrogen transfer reactions of 2 to give alpha-amide radicals compete with decarboxylation; cyclization of an alpha-amide radical thus formed also is reported. The Lewis acid MgBr2 can reduce the 1,5-hydrogen atom transfer reaction apparently by a chelation effect on the precursor that leads to production of radical 2 in a conformation unfavorable for hydrogen atom transfer. By appropriate experimental design, radicals 2 often can be directed toward one desired reaction, and several relative rate constants for reactions of 2 necessary for such design were determined in this work.

  DOI：

  10.1021/jo00089a023
• 作为产物：
  描述：

  4-戊烯酸 、 正丁胺 在 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-butylpent-4-enamide
  参考文献：
  名称：

  在温和条件下通过仲酰胺的活化直接区域选择性合成四唑鎓盐

  摘要：

  四唑盐是具有生物活性的分子，在生化分析中已发现了广泛的应用。通过正式的（3 + 2）环加成反应描述了四唑鎓盐的区域选择性合成。使用简单的酰胺和叠氮化物作为起始原料的可能性以及温和的条件允许宽泛的官能团耐受性。

  DOI：

  10.1021/acs.orglett.7b01004

文献信息

• Repurposing the 3‐Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification
  作者：Mengyi Zhu、Lijuan Wang、Jing He

  DOI：10.1002/anie.202010042

  日期：2021.1.25

  molecules with novel skeletons, but also to identify the enzymes that catalyze diverse chemical reactions. Exploring the substrate promiscuity and catalytic mechanism of those biosynthetic enzymes facilitates the development of potential biocatalysts. SfaB is an acyl adenylate‐forming enzyme that adenylates a unique building block, 3‐isocyanobutanoic acid, in the biosynthetic pathway of the diisonitrile

  微生物天然产物的基因组挖掘使化学家不仅能够发现具有新颖骨架的生物活性分子，而且能够识别催化多种化学反应的酶。探索这些生物合成酶的底物混杂性和催化机理有助于开发潜在的生物催化剂。SfaB是一种形成酰基腺苷酸的酶，可在由硫链霉菌产生的二异腈自然产物SF2768的生物合成途径中，对独特的结构单元3-异氰基丁酸进行腺苷酸化。，并且该AMP连接酶被证明可以接受各种短链脂肪酸（SCFA）。在本文中，我们将SfaB重新用于催化那些SCFA与各种胺或硫醇亲核试剂之间的酰胺化或硫酯化反应，从而提供了另一种酶促方法来体外制备相应的酰胺和硫酯。
• Electroreductive Olefin–Ketone Coupling
  作者：Pengfei Hu、Byron K. Peters、Christian A. Malapit、Julien C. Vantourout、Pan Wang、Jinjun Li、Lucas Mele、Pierre-Georges Echeverria、Shelley D. Minteer、Phil S. Baran

  DOI：10.1021/jacs.0c11214

  日期：2020.12.16

  A user-friendly approach is presented to sidestep the venerable Grignard addition to unactivated ketones to access tertiary alcohols by reversing the polarity of the disconnection. In this work a ketone instead acts as a nucleophile when adding to simple unactivated olefins to accomplish the same overall transformation. The scope of this coupling is broad as enabled using an electrochemical approach

  提出了一种用户友好的方法，通过反转断开的极性来避开古老的格氏加成法，以获取未活化酮的叔醇。在这项工作中，当加入简单的未活化烯烃以完成相同的整体转化时，酮反而充当亲核试剂。这种耦合的范围很广，因为使用电化学方法可以实现，并且反应是可扩展的、化学选择性的，并且不需要排除空气或水的预防措施。多项应用证明了多步合成反应的简化性质，机理研究指出了一种直观的机制，让人联想到其他化学还原剂，如 SmI2（不能完成相同的反应）。
• Direct Transformation of Secondary Amides into Secondary Amines: Triflic Anhydride Activated Reductive Alkylation
  作者：Kai-Jiong Xiao、Ai-E Wang、Pei-Qiang Huang

  DOI：10.1002/anie.201204098

  日期：2012.8.13

  transformation has been developed (see scheme; 2‐F‐Py=2‐fluoropyridine; Tf=trifluorosulfonyl). The amines are synthesized in good yields and the ketimine intermediates can be isolated before the reduction. This method should find applications in the synthesis of nitrogen‐containing bioactive molecules and medicinal agents.

  通用且温和：已开发出标题转化的第一个通用方法（请参阅方案； 2-F-Py = 2-氟吡啶； Tf =三氟磺酰基）。胺以高收率合成，并且在还原前可以分离出酮亚胺中间体。该方法应在合成含氮生物活性分子和药物中找到应用。
• Amidyl radicals from N-(phenylthio)amides
  作者：John L. Esker、Martin Newcomb

  DOI：10.1016/s0040-4039(00)91819-7

  日期：1993.10

  Preparations on N-(phenylthio)amides from secondary amides are described, and these species are shown to be efficient precursors for amidyl radicals in Bu3SnH mediated reactions; cyclizations of δ,ε-unsaturated amidyl radicals from these precursors and their use in measurement of relative rate constants are reported.

  描述了由仲酰胺在N-（苯硫基）酰胺上的制备，这些物质被证明是Bu 3 SnH介导的反应中酰胺基自由基的有效前体。报道了来自这些前体的δ，ε-不饱和酰胺基的环化及其在相对速率常数的测量中的应用。
• Intramolecular electrophilic cyclization of functional derivatives of unsaturated compounds: II. Synthesis and transformation of N-{(2Z)-5-[(arylsulfanyl)methyl]dihydrofuran-2(3H)-ylidene}-N-alkyl(aryl)aminium perchlorates
  作者：A. I. Vas’kevich、N. M. Tsizorik、E. B. Rusanov、V. I. Staninets、M. V. Vovk

  DOI：10.1134/s1070428012020078

  日期：2012.2

  N-Alkyl(aryl)amides of allylacetic acid when reacting with arylsulfenyl chlorides in acetic acid in the presence of lithium perchlorate undergo a selective cyclization to form N-(2Z)-5-[(arylsulfanyl)methyl] dihydrofuran-2(3H)-ylidene}-N-alkyl-(aryl)aminium perchlorates. Treating of the latter with sodium acetate leads to the formation of the corresponding 5-[(arylsulfanyl)methyl]lactones, and with

  在高氯酸锂存在下与乙酸中的芳基亚硫酰氯反应时，烯丙酸的N-烷基（芳基）酰胺经过选择性环化反应生成N -（2 Z）-5-[（芳基硫烷基）甲基]二氢呋喃-2（ 3 H）-亚烷基} -N-烷基-（芳基）高氯酸铵。后者用乙酸钠处理导致形成相应的5-[（（芳基硫烷基）甲基]内酯，并用乙酸乙酯处理成5-[（（芳基硫烷基）甲基] -2-亚氨基内酯。与仲环烷基胺在水的存在下反应，发生氨基转移和四氢呋喃开环，得到5-芳基硫烷基-4-羟基戊酸酰胺。