N-(3-phenylpropyl)-cyclohexanecarboxamide

• 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)-cyclohexanecarboxamide
• 英文别名: N-(3-phenylpropyl)cyclohexanecarboxamide
• 化学式: C₁₆H₂₃NO
• mdl: MFCD01348492
• 分子量: 245.365
• InChiKey: SNKRIYZXSMDMTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  3-苯基-1-丙胺 、 环己甲酸 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到N-(3-phenylpropyl)-cyclohexanecarboxamide
  参考文献：
  名称：

  使用吡啶-3-羧酸酐 (3-PCA) 进行脱水缩合的有效方法：由几乎等摩尔量的羧酸和胺合成甲酰胺

  摘要：

  在 4-(二甲胺) 存在下，使用吡啶-3-羧酸酐 (3-PCA) 建立了一种从各种羧酸和胺制备甲酰胺的非常有用的方法。

  DOI：

  10.1246/cl.2007.658

文献信息

• Highly Efficient Method for the Synthesis of Carboxamides from Carboxylic Acids and Amines Using Benzenesulfonic Anhydride (BSA)
  作者：Setsuo Funasaka、Koji Kato、Teruaki Mukaiyama

  DOI：10.1246/cl.2007.1456

  日期：2007.12.5

  A highly efficient method by using benzenesulfonic anhydride (BSA) in the presence of 4-(dimethylamino)pyridine (DMAP) to synthesize carboxamides from various carboxylic acids and amines including ...

  一种在 4-（二甲氨基）吡啶 (DMAP) 存在下使用苯磺酸酐 (BSA) 从各种羧酸和胺合成羧酰胺的高效方法，包括...
• An Effective Method for the Synthesis of Carboxamides by Using Tetrakis(pyridine-2-yloxy)silane as a Mild Coupling Reagent
  作者：Takashi Tozawa、Yoshinobu Yamane、Teruaki Mukaiyama

  DOI：10.1246/cl.2005.1334

  日期：2005.10

  Tetrakis(pyridin-2-yloxy)silane [Si(OPy)4] is easily prepared by trans-silylation between silicon tetrachloride and trimethyl(pyridin-2-yloxy)silane in the molar ratio of 1:4. This novel reagent is effectively employed as a mild dehydrating reagent in forming various carboxamides from the corresponding carboxylic acids and amines that involve secondary or tertiary alkyl substituted ones in good to high yields without using any basic promoters such as tertiary amines or 4-(dimethylamino)pyridine.

  四(吡啶-2-氧基)硅烷[Si(OPy)4]可通过硅四氯化物与三甲基(吡啶-2-氧基)硅烷在1:4的摩尔比下通过反式硅基化轻松制备。这种新型试剂有效地用作温和脱水剂，在无需使用叔胺或4-(二甲基氨基)吡啶等碱性促进剂的情况下，以良好至高产率形成各种羧酰胺，涉及含有二级或三级烷基取代的相应羧酸和胺。
• A Convenient Method for the Synthesis of Carboxamides and Thioesters by Using Tetrakis(2-methylimidazol-1-yl)silane
  作者：Teruaki Mukaiyama、Takashi Tozawa、Yoshinobu Yamane

  DOI：10.3987/com-05-s(t)31

  日期：——
• 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.