N-(3-phenylpropyl)cyclopropanecarboxamide | 495381-81-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-phenylpropyl)cyclopropanecarboxamide
• 英文别名: N-phenylpropylcyclopropane carboxamide
• CAS: 495381-81-2
• 化学式: C₁₃H₁₇NO
• mdl: MFCD02372626
• 分子量: 203.284
• InChiKey: QMXJWCYAYZWVIW-UHFFFAOYSA-N

物化性质

• 溶解度：
  >30.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  羟甲基环丙烷 、 苯代丙腈 在 RuH₂(CO)(PPh₃)₃ 、 sodium hydride 、 1,3-diisopropylimidazolium bromide 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以79%的产率得到N-(3-phenylpropyl)cyclopropanecarboxamide
  参考文献：
  名称：

  Ruthenium-Catalyzed Redox-Neutral and Single-Step Amide Synthesis from Alcohol and Nitrile with Complete Atom Economy

  摘要：

  A completely atom-economical and redox-neutral catalytic amide synthesis from an alcohol and a nitrite is realized. The amide C-N bond is efficiently formed between the nitrogen atom of nitrile and the alpha-carbon of alcohol, with the help of an N-heterocyclic carbene-based ruthenium catalyst, without a single by-product. A utility of the reaction was demonstrated by synthesizing C-13 or N-15 isotope-labeled amides without involvement of any separate reduction and oxidation step.

  DOI：

  10.1021/ja404695t

文献信息

• N-Heterocyclic carbene-based well-defined ruthenium hydride complexes for direct amide synthesis from alcohols and amines under base-free conditions
  作者：Kunsoon Kim、Byungjoon Kang、Soon Hyeok Hong

  DOI：10.1016/j.tet.2015.02.016

  日期：2015.7

  carbene-based ruthenium(II) hydride complexes were developed for amide synthesis from alcohols and amines under base-free conditions. Diverse amides were synthesized in fair-to-excellent yields. In the case of secondary amines, where direct dehydrogenative amidation is not feasible, a catalytic amount of a base was required to promote the transamidation of esters, which are byproducts of alcohol dimerization

  为在无碱条件下从醇和胺合成酰胺而开发了易于合成的，定义明确的基于N-杂环卡宾的氢化钌（II）配合物。合成了各种酰胺，收率相当理想。在仲胺的情况下，直接脱氢酰胺化是不可行的，需要催化量的碱来促进酯的氨基转移，所述酯是醇二聚的副产物。
• 高压环境下离子液体催化制备酰胺类化合物的方法
  申请人：烟台大学

  公开号：CN112209847B

  公开（公告）日：2022-12-23

  一种高压环境下离子液体催化制备酰胺类化合物的方法。本方法以离子液体1‑乙基‑3‑甲基咪唑鎓乙酸盐作为催化剂和溶剂，以氧气为氧化剂，在高压和加热条件下，将芳香甲醇或烷基醇转化为酰胺类化合物。本发明所述的合成方法本方法的原料与技术成本低廉；无需使用有毒重金属催化剂，远较其他传统方法安全低毒，经济环保；本方法步骤少，操作简便，有利于大规模合成，对于酰胺类化合物的合成与制备的大型工业化具有重要意义。
• Structure−Activity Relationships of Cycloalkylamide Derivatives as Inhibitors of the Soluble Epoxide Hydrolase
  作者：In-Hae Kim、Yong-Kyu Park、Bruce D. Hammock、Kosuke Nishi

  DOI：10.1021/jm101431v

  日期：2011.3.24

  Structure-activity relationships of cycloalkylamide compounds as inhibitors of human sEH were investigated. When the left side of amide function was modified by a variety of cycloalkanes, at least a C6 like cyclohexane was necessary to yield reasonable inhibition potency on the target enzyme. In compounds with a smaller cycloalkane or with a polar group on the left side of amide function, no inhibition was observed. On the other hand, increased hydrophobicity dramatically improved inhibition potency. Especially, a tetrahydronaphthalene (20) effectively increased the potency. When a series of alkyl or aryl derivatives of cycloalkylamide were investigated to continuously optimize the right side of the amide pharmacophore, a benzyl moiety functionalized with a polar group produced highly potent inhibition. A nonsubstituted benzyl, alkyl, aryl, or biaryl structure present on the right side of the cycloalkylamide function induced a big decrease in inhibition potency. Also, the resulting potent cycloalkylamide (32) showed reasonable physical properties.
• Ruthenium-Catalyzed Redox-Neutral and Single-Step Amide Synthesis from Alcohol and Nitrile with Complete Atom Economy
  作者：Byungjoon Kang、Zhenqian Fu、Soon Hyeok Hong

  DOI：10.1021/ja404695t

  日期：2013.8.14

  A completely atom-economical and redox-neutral catalytic amide synthesis from an alcohol and a nitrite is realized. The amide C-N bond is efficiently formed between the nitrogen atom of nitrile and the alpha-carbon of alcohol, with the help of an N-heterocyclic carbene-based ruthenium catalyst, without a single by-product. A utility of the reaction was demonstrated by synthesizing C-13 or N-15 isotope-labeled amides without involvement of any separate reduction and oxidation step.