N-cyclohexylhippuramide | 842-98-8

• 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-cyclohexylhippuramide
• 英文别名: Hippursaeure-cyclohexylamid；N-Cyclohexyl-hippursaeureamid；Hippursaeure-N-cyclohexylamid；Hippuryl-cyclohexylamid；N-(2-cyclohexylamino-2-oxoethyl)benzamide；N²-Cyclohexyl-hippursaeureamid；hippuric acid cyclohexylamide；N-[2-(cyclohexylamino)-2-oxoethyl]benzamide
• CAS: 842-98-8
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: KGKLIJQTNNUQPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  马尿酸 在 乙酸乙酯 、 三乙胺 作用下， 生成 N-cyclohexylhippuramide
  参考文献：
  名称：

  关于活化的酯。三，氨基酸和肽衍生物的活化酯与胺和氨基酸酯的反应

  摘要：

  使许多氨基酸和肽衍生物的活化酯与各种有机胺，包括氨基酸酯反应。获得的良好收率和温和的反应条件使得活化的酯化酰化方法似乎可以在肽合成中很好地使用。芳香胺和仲胺的氨解仅缓慢进行，但是通过强叔胺和酸的催化作用可大大促进该反应。

  DOI：

  10.1002/hlca.19550380111

文献信息

• The Ugly Duckling Metamorphosis: The Ammonia/Formaldehyde Couple Made Possible in Ugi Reactions.
  作者：Thaissa Pasquali F. Rosalba、Samia Sayegh A. Kas、Ana Beatriz S. Sampaio、Carlos Eduardo M. Salvador、Carlos Kleber Z. Andrade

  DOI：10.1002/ejoc.202001671

  日期：2021.5.26

  The ammonia/formaldehyde couple (the ugly duckling in Ugi reactions) was finally made possible using hexamethylenetetramine (HMTA) as an efficient formaldehyde surrogate. Various NH-free Ugi adducts were obtained in moderate to excellent yields and two of them were converted to diketopiperazines (DKPs).

  最终，使用六亚甲基四胺（HMTA）作为有效的甲醛替代物，可以使氨/甲醛对（在Ugi反应中为丑小鸭）成为可能。以中等至极高的收率获得了各种不含NH的Ugi加合物，其中两个被转化为二酮哌嗪（DKPs）。
• Über aktivierte Ester. III. Umsetzungen aktivierter Ester von Aminosäure- und Peptid-Derivaten mit Aminen und Aminosäureestern
  作者：R. Schwyzer、M. Feurer、B. Iselin

  DOI：10.1002/hlca.19550380111

  日期：——

  A number of activated esters of amino acid and peptide derivatives were reacted with various organic amines, including amino acid esters. The good yields obtained, and the mild reaction conditions make it seem possible that the activated ester method of acylation may be of good use in peptide synthesis. Aminolysis by aromatic amines and by secondary amines proceeds only slowly, but the reaction can

  使许多氨基酸和肽衍生物的活化酯与各种有机胺，包括氨基酸酯反应。获得的良好收率和温和的反应条件使得活化的酯化酰化方法似乎可以在肽合成中很好地使用。芳香胺和仲胺的氨解仅缓慢进行，但是通过强叔胺和酸的催化作用可大大促进该反应。
• Mechanistic insight into benzenethiol catalyzed amide bond formations from thioesters and primary amines
  作者：Nicolai Stuhr-Hansen、Nicolai Bork、Kristian Strømgaard

  DOI：10.1039/c4ob00073k

  日期：——

  The influence of arylthiols on cysteine-free ligation, i.e. the reaction between an alkyl thioester and a primary amine forming an amide bond, was studied in a polar aprotic solvent. We reacted the ethylthioester of hippuric acid with cyclohexylamine in the absence or presence of various quantities of thiophenol (PhSH) in a slurry of disodium hydrogen phosphate in dry DMF. Quantitative conversions into the resulting amide were observed within a few hours in the presence of equimolar amounts of thiophenol. Ab initio calculations showed that the reaction mechanism in DMF is similar to the well-known aqueous reaction mechanism. The energy barrier of the catalyzed amidation reaction is approximately 40 kJ mol−1 lower than the non-catalyzed amidation reaction. At least partially this can be explained by a hydrogen bond from the amine to the π-electrons of the thiophenol, stabilizing the transition state in the aromatic thioester amidation reaction. Under similar conditions, cysteine-free ligation was achieved by coupling a fully side-chain protected 15 amino acid phosphopeptide thioester to the free N-terminal of a side-chain protected 9 amino acid peptide producing the corresponding 24 amino acid phosphopeptide.

  在极性非质子溶剂中研究了芳硫醇对无半胱氨酸连接（即烷基硫酯和伯胺之间形成酰胺键的反应）的影响。我们在存在或不存在不同量的苯硫酚 (PhSH) 的情况下，在磷酸氢二钠在干燥 DMF 中的浆液中，使马尿酸乙硫酯与环己胺反应。在等摩尔量的苯硫酚存在下，在几个小时内观察到定量转化为所得酰胺。从头计算表明，DMF 中的反应机理与众所周知的水溶液反应机理相似。催化酰胺化反应的能垒比非催化酰胺化反应低约40 kJ mol−1。这至少部分可以通过从胺到苯硫酚的π电子的氢键来解释，从而稳定了芳香族硫酯酰胺化反应中的过渡态。在类似条件下，通过将完全侧链保护的 15 个氨基酸磷酸肽硫酯偶联到侧链保护的 9 个氨基酸肽的游离 N 端，产生相应的 24 个氨基酸磷酸肽，实现无半胱氨酸连接。
• Waldschmidt-Leitz; Kuehn, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1950, vol. 285, p. 23,31
  作者：Waldschmidt-Leitz、Kuehn

  DOI：——

  日期：——
• Catalyst and solvent-free amidation of inactive esters of N-protected amino acids
  作者：Krishna Chaitanya Nadimpally、Kishore Thalluri、Nani Babu Palakurthy、Abhijit Saha、Bhubaneswar Mandal

  DOI：10.1016/j.tetlet.2011.03.039

  日期：2011.5

  A catalyst free procedure for the preparation of amides from inactive esters of N-protected amino acids and various amines is demonstrated under mild reaction conditions. Our effort to recover excess amine and generated alcohol is an approach towards environment friendly and cost effective synthesis under easy operational conditions.

  在温和的反应条件下，证明了由N保护的氨基酸和各种胺的非活性酯制备酰胺的无催化剂方法。我们努力回收过量的胺和生成的醇是一种在简单的操作条件下实现环境友好且具有成本效益的合成方法。