N-tert-butylhexadecanamide | 74058-70-1

• 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-tert-butylhexadecanamide
• 英文别名: hexadecanoic acid N-(tert-butyl)amide；Hexadecanoic acid tert-butylamide
• CAS: 74058-70-1
• 化学式: C₂₀H₄₁NO
• 分子量: 311.552
• InChiKey: PWSZYBZCNJXAJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 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-tert-butylhexadecanamide 、 三氯氧磷 以94%的产率得到
  参考文献：
  名称：

  PERNI, R. B.;GRIBBLE, G. W., ORG. PREP. AND PROCED. INT., 1983, 15, N 5, 297-302

  摘要：

  DOI：
• 作为产物：
  描述：

  棕榈酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 70.0h， 生成 N-tert-butylhexadecanamide
  参考文献：
  名称：

  Monitored aminolysis of 3-acylthiazolidine-2-thione : A new convenient synthesis of amide

  摘要：

  DOI：

  10.1016/s0040-4039(00)71520-6

文献信息

• HIGH CHEMOSELECTIVE SYNTHESIS OF CARBOXAMIDES BY USING<i>SYN</i>-PHENYLPYRIDYL-<i>O</i>-ACYL OXIMES(PPKO)
  作者：Tadayo Miyasaka、Shunsaku Noguchi

  DOI：10.1246/cl.1985.701

  日期：1985.6.5

  Various carboxamides are prepared chemoselectively in good yields by using syn-phenylpyridyl ketoxime(PPKO) as functional leaving group.

  通过使用反式-苯基吡啶酮肟（PPKO）作为功能性离去基团，可以化学选择性地制备多种羧酰胺，并获得良好的产率。
• Mass spectral characterization of fatty acid amides from alfalfa trichomes and their deterrence against the potato leafhopper
  作者：Christopher M. Ranger、Rudolph E.K. Winter、George E. Rottinghaus、Elaine A. Backus、David W. Johnson

  DOI：10.1016/j.phytochem.2005.01.012

  日期：2005.3

  surfaces treated with the synthetic amides or an untreated control. N-(3-methylbutyl)amides and N-(2-methylpropyl)amides of C14 through C18 fatty acids did not deter leafhopper settling in a dose-dependent fashion. In contrast, when tested singly, N-(3-methylbutyl)amide of linoleic acid exhibited dose-dependent deterrence against leafhopper settling. Fatty acid amides localized in alfalfa glandular trichomes

  正常饱和 C14、C15、C16、C17 和 C18 脂肪酸的同源系列 N-（3-甲基丁基）酰胺被鉴定为来自紫花苜蓿 G98A 腺毛状体提取物的主要成分，紫花苜蓿 G98A 是一种抗马铃薯叶蝉 Empoasca 的苜蓿基因型蚕豆。C14 到 C18 正常脂肪酸的第二个同源系列的 N-(2-甲基丙基)酰胺是次要成分。饱和游离脂肪酸 C12、C13、C14、C15、C16、C17 和 C18 以痕量存在，亚油酸的 N-(3-甲基丁基)酰胺 (C18:2) 也是如此。C14 到 C18 脂肪酸的 N-(3-甲基丁基)酰胺和 N-(2-甲基丙基)酰胺，以及亚油酸的 N-(3-甲基丁基)酰胺，通过应用这些化合物合成和生物测定对叶蝉的威慑作用到含有人工食物的小袋表面。然后在用合成酰胺处理的饮食表面或未处理的对照之间为叶蝉提供了两种选择。C14 到 C18 脂肪酸的 N-(3-甲基丁基) 酰胺和 N-(2-甲基丙基)
• Nagao, Yoshimitsu; Seno, Kaoru; Kawabata, Kohji, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 7, p. 2687 - 2699
  作者：Nagao, Yoshimitsu、Seno, Kaoru、Kawabata, Kohji、Miyasaka, Tadao、Takao, Sachiko、Fujita, Eiichi

  DOI：——

  日期：——
• 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.
• MIYASAKA, TADAYO;NOGUCHI, SHUNSAKU, CHEM. LETT., 1985, N 6, 701-704
  作者：MIYASAKA, TADAYO、NOGUCHI, SHUNSAKU

  DOI：——

  日期：——