N-methoxyhexadecanamide | 337962-52-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-methoxyhexadecanamide
• 英文别名: Hexadecanoic acid methoxy-amide
• CAS: 337962-52-4
• 化学式: C₁₇H₃₅NO₂
• 分子量: 285.47
• InChiKey: HLQXLEOFBLMNDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethynyl-1,2-benziodoxol-3(1H)-one 、 N-methoxyhexadecanamide 在 potassium carbonate 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以57%的产率得到(Z)-N-(1-vin-2-yl)-N-methoxyhexadecanamide-1,2-benziodoxol-3-(1H)-one
  参考文献：
  名称：

  异羟肟酸衍生物与乙炔基苯并恶唑啉酮的N-烯基化反应可通过乙烯基苯并恶唑啉酮合成顺式酰胺

  摘要：

  本文报道了在乙炔基苯并恶唑啉酮-乙腈络合物（EBX-MeCN）存在下，由O-烷基异羟肟酸立体合成顺式-β- N-烷氧基酰胺乙烯基苯并恶唑烷（顺式-β - N -RO-酰胺-VBXs）。反应在温和的条件下进行，所述条件包括水性溶剂，温和的碱和室温。该反应容许各种衍生自羧酸的O-烷基异羟肟酸，例如氨基酸，药物和天然产物。还使用氧化氘作为氘源合成了乙烯基双氘化的顺式-β - N -MeO-酰胺-VBXs。缬氨酸衍生的顺式将-β - N - MeO-酰胺-VBX立体定向衍生为异羟肟酸衍生的顺式-酰胺，而不会失去立体选择性或降低氘/氢比。

  DOI：

  10.1039/d1ob00055a
• 作为产物：
  描述：

  棕榈酸 在 氯化亚砜 、 potassium carbonate 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 N-methoxyhexadecanamide
  参考文献：
  名称：

  异羟肟酸衍生物与乙炔基苯并恶唑啉酮的N-烯基化反应可通过乙烯基苯并恶唑啉酮合成顺式酰胺

  摘要：

  本文报道了在乙炔基苯并恶唑啉酮-乙腈络合物（EBX-MeCN）存在下，由O-烷基异羟肟酸立体合成顺式-β- N-烷氧基酰胺乙烯基苯并恶唑烷（顺式-β - N -RO-酰胺-VBXs）。反应在温和的条件下进行，所述条件包括水性溶剂，温和的碱和室温。该反应容许各种衍生自羧酸的O-烷基异羟肟酸，例如氨基酸，药物和天然产物。还使用氧化氘作为氘源合成了乙烯基双氘化的顺式-β - N -MeO-酰胺-VBXs。缬氨酸衍生的顺式将-β - N - MeO-酰胺-VBX立体定向衍生为异羟肟酸衍生的顺式-酰胺，而不会失去立体选择性或降低氘/氢比。

  DOI：

  10.1039/d1ob00055a

文献信息

• Site Selectivity in the Synthesis of <i>O</i>-Methylated Hydroxamic Acids with Diazomethane
  作者：Antonella Leggio、Angelo Liguori、Anna Napoli、Carlo Siciliano、Giovanni Sindona

  DOI：10.1021/jo0012391

  日期：2001.4.1

  this paper we report the results obtained by treating some selected hydroxamic acids with diazomethane in ethereal media. The multitask reagent diazomethane was used either as a base to induce deprotonation of the chosen hydroxamic acids or as conjugated acid which undergoes one-pot methylation processes of the generated anions. Product distributions clearly showed that a high site selectivity is expressed

  在本文中，我们报告了通过在重介质中用重氮甲烷处理某些选定的异羟肟酸获得的结果。多任务试剂重氮甲烷既可以用作碱诱导所选的异羟肟酸去质子化，也可以用作共轭酸，该共轭酸经过一锅法对生成的阴离子进行甲基化。产物分布清楚地表明，在烷基化过程中，不同的去质子化物质表现出高的位点选择性。在所采用的条件下，在所有情况下，甲基化的普遍位点是异羟肟酸的氧。虽然在脂族异羟肟酸中仅观察到O-烷基化，但在芳族底物中，NH基团与OH的亲核位点竞争，尽管OH反应性仍然占主导地位。
• Modifications of the Ethanolamine Head in <i>N</i>-Palmitoylethanolamine:  Synthesis and Evaluation of New Agents Interfering with the Metabolism of Anandamide
  作者：Séverine Vandevoorde、Kent-Olov Jonsson、Christopher J. Fowler、Didier M. Lambert

  DOI：10.1021/jm0209679

  日期：2003.4.1

  The endogenous fatty acid amide anandamide (AEA) has, as a result of its actions on cannabinoid and vanilloid receptors, a number of important pharmacological properties including effects on nociception, memory processes, spasticity, and cell proliferation. Inhibition of the metabolism of AEA, catalyzed by fatty acid amide hydrolase (FAAH), potentiates the actions of AEA in vivo and therefore may be a useful target for drug development. In the present study, we have investigated whether substitution of the headgroup of the endogenous alternative FAAH substrate palmitoylethanolamide (PEA) can result in the identification of novel compounds preventing AEA metabolism. Thirty-seven derivatives of PEA were synthesized, with the C16 long chain of palmitic acid kept intact, and comprising 20 alkylated, 12 aromatic, and 4 halogenated amides. The ability of the PEA derivatives to inhibit FAAH-catalyzed hydrolysis of [H-3]AEA was investigated using rat brain homogenates as a source of FAAH. Inhibition curves were analyzed to determine the potency of the inhibitable fraction (pI(50) values) and the maximal attained inhibition for the compound, given that solubility in an aqueous environment is a major issue for these compounds. In the alkylamide family, palmitoylethyl-amide and palmitoylallylamide were inhibitors of AEA metabolism with PI50 values of 5.45 and 5.47, respectively. Halogenated derivatives (Cl and Br) exhibit PI50 values of similar to5.5 but rather low percentages of maximal inhibition. The -OH group of the ethyl head chain of N-palmitoylethanolamine was not necessary for interaction with FAAH. Amides containing aromatic moieties were less potent inhibitors of AEA metabolism. Compounds containing amide and ester bonds, 13 and 37, showed PI50 values of 4.99 and 5.08, respectively. None of the compounds showed obvious affinity for CB1 or CB2 receptors expressed on Chinese hamster ovary (CHO) cells. It is concluded that although none of the compounds were dramatically more potent than PEA itself at reducing the metabolism of AEA, the lack of effect of the compounds at CB1 and CB2 receptors makes them useful templates for development of possible therapeutic FAAH inhibitors.
• <i>N</i>-Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesize <i>cis</i>-enamides through vinyl benziodoxolones
  作者：Daisuke Shimbo、Toshifumi Maruyama、Norihiro Tada、Akichika Itoh

  DOI：10.1039/d1ob00055a

  日期：——

  (cis-β-N-RO-amide-VBXs) from O-alkyl hydroxamic acids in the presence of an ethynyl benziodoxolone–acetonitrile complex (EBX–MeCN) is reported herein. The reaction was performed under mild conditions including an aqueous solvent, a mild base, and room temperature. The reaction tolerated various O-alkyl hydroxamic acids derived from carboxylic acids, such as amino acids, pharmaceuticals, and natural products

  本文报道了在乙炔基苯并恶唑啉酮-乙腈络合物（EBX-MeCN）存在下，由O-烷基异羟肟酸立体合成顺式-β- N-烷氧基酰胺乙烯基苯并恶唑烷（顺式-β - N -RO-酰胺-VBXs）。反应在温和的条件下进行，所述条件包括水性溶剂，温和的碱和室温。该反应容许各种衍生自羧酸的O-烷基异羟肟酸，例如氨基酸，药物和天然产物。还使用氧化氘作为氘源合成了乙烯基双氘化的顺式-β - N -MeO-酰胺-VBXs。缬氨酸衍生的顺式将-β - N - MeO-酰胺-VBX立体定向衍生为异羟肟酸衍生的顺式-酰胺，而不会失去立体选择性或降低氘/氢比。