N-十八烷基乙酰胺 | 3906-22-7

• 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
• 中文名称: N-十八烷基乙酰胺
• 英文名称: N-octadecylacetamide
• 英文别名: N-Octadecyl-acetamid；N-stearylacetamide；N-octadecyl-acetyl-amide
• CAS: 3906-22-7
• 化学式: C₂₀H₄₁NO
• 分子量: 311.552
• InChiKey: NOSILEXHUBACKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  22
• 可旋转键数：
  17
• 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

安全信息

• 海关编码：
  2924199090
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  N-十八烷基乙酰胺 在 三氧化二氮 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 生成 N-Nitroso-N-acetyl-octadecylamin
  参考文献：
  名称：

  Reimlinger,H., Chemische Berichte, 1960, vol. 93, p. 1857 - 1869

  摘要：

  DOI：
• 作为产物：
  描述：

  十八烷胺乙酸酯 生成 N-十八烷基乙酰胺
  参考文献：
  名称：

  Hunter, Iowa State College Journal of Science, 1941, vol. 15, p. 228 - 230

  摘要：

  DOI：

文献信息

• Environmentally benign decarboxylative <i>N</i>-, <i>O</i>-, and <i>S</i>-acetylations and acylations
  作者：Santanu Ghosh、Anisha Purkait、Chandan K. Jana

  DOI：10.1039/d0gc03731a

  日期：——

  An operationally simple and general method for acetylation and acylation of a wide variety of substrates (amines, alcohols, phenols, thiols, and hydrazones) has been reported. Meldrum's acid and its derivatives have been used as an air-stable, non-volatile, cost-effective, and easy to handle acetylating/acylating agent. Easily separable byproducts (CO2 and acetone) allowed the isolation of analytically

  已经报道了用于多种底物（胺，醇，酚，硫醇和）的乙酰化和酰化的操作简单且通用的方法。Meldrum的酸及其衍生物已被用作空气稳定，不挥发，具有成本效益且易于处理的乙酰化/酰化剂。易于分离的副产物（CO 2和丙酮）可分离分析纯的乙酰化产物，而无需进行后处理和任何色谱分离。
• Hydrolysis and Stability of Acetylsalicylic Acid in Stearylamine-containing Liposomes
  作者：Muhammad J Habib、James A Rogers

  DOI：10.1111/j.2042-7158.1993.tb05586.x

  日期：2011.4.12

  The hydrolysis and the stabilization of acetylsalicylic acid (ASA) in liposomes at 30°C were studied. The liposomes consisted of dimyristoylphosphatidylcholine (DMPC) and stearylamine. At pH 4·0 and 8·0, the pseudo-first-order rate constants (kobs) in DMPC: stearylamine (2:1 mole ratio) liposomes were approximately 60% of the values in control solutions (kB) if ASA was incorporated via the organic phase. In contrast, when ASA was added via the aqueous phase, kobs = kB at pH 4·0 but kobs &lt; kB at pH 8·0 and kobs increased with the fraction of stearylamine in the liposomes. However, when ASA was added via the organic phase, reactions occurred which resulted in the loss of ASA as a function of the time period between phase admixture and the point of film hydration. A product of the reactions was determined by IR and TLC to be N-stearylacetamide. Both the initial loss of ASA and the increase in stability decreased as the DMPC: stearylamine mole ratio increased. A mechanism of aminolysis occurring in the organic solvent and at liposome surfaces between ASA and stearylamine or DMPC at pH 8·0 has been suggested. It is concluded that the orientation of ASA and the ordered structural environment of the bilayers minimizes the aminolytic and hydrolytic reactions.

  研究了30°C下乙酰水杨酸（ASA）在磷脂酰胆碱（DMPC）和硬脂胺组成的脂质体中的水解和稳定性。在pH 4·0和8·0时，如果ASA通过有机相引入，DMPC：硬脂胺（2:1摩尔比）脂质体中的伪一级速率常数（kobs）约为对照溶液（kB）的60%。相比之下，当ASA通过水相添加时，在pH 4·0时kobs = kB，而在pH 8·0时kobs &lt; kB，且kobs随脂质体中硬脂胺比例的增加而增加。然而，当ASA通过有机相添加时，发生的反应导致ASA随相混合和膜水化点之间时间段的增加而损失。通过IR和TLC确定反应产物为N-硬脂基乙酰胺。随着DMPC：硬脂胺摩尔比的增加，ASA的初始损失和稳定性的增加都降低。提出了一种在有机溶剂中以及在pH 8·0时脂质体表面ASA与硬脂胺或DMPC之间的胺解机制的假设。可以得出结论，ASA的取向和双层有序结构环境最小化了胺解和水解反应。

• Chemoselective N-deacetylation under mild conditions
  作者：Prakash R. Sultane、Trimbak B. Mete、Ramakrishna G. Bhat

  DOI：10.1039/c3ob41971a

  日期：——

  A mild and efficient chemoselective N-deacetylation using the Schwartz reagent at room temperature in rapid time is described. The mild and neutral conditions enable orthogonal N-deacetylation in the presence of some of the common protecting groups (viz. Boc, Fmoc, Cbz, Ts). The deprotection conditions did not induce any epimerization at the chiral amino centre.

  描述了一种温和高效的化学选择性去乙酰化方法，该方法使用施瓦茨试剂在室温下迅速进行。温和和中性的条件使得在一些常见保护基团（即Boc、Fmoc、Cbz、Ts）存在的情况下能够进行正交去乙酰化。去保护条件不会引起手性氨基中心的任何表异构化。
• Hydrophobic Effect and Substrate Specificity in Reaction of Thioester and Amine in Water
  作者：Atsushi Torihata、Chiaki Kuroda

  DOI：10.1246/bcsj.20100143

  日期：2010.12.15

  extent of hydrophobic effect in amidation reaction of alkyl thioester with alkylamine in water was studied. The yield of the products was primarily dependent on the alkyl group of amine. For example, the reaction of S-dodecyl dodecanethioate with dodecylamine proceeded in good yield, while the reaction did not occur with cyclohexylamine, piperidine, and dipropylamine. The effect of chain length of n-alkylamine

  研究了烷基硫酯与烷基胺在水中的酰胺化反应中疏水作用的程度。产物的产率主要取决于胺的烷基。例如，S-十二烷基硫代酸酯与十二烷基胺的反应收率良好，而与环己胺、哌啶和二丙胺的反应则没有发生。研究了正烷基胺链长的影响以表明存在疏水作用。酰胺的产率也次要取决于硫酯的烷基，但影响比胺小。
• Decreased Stability in Liposomal Suspensions: Accelerated Loss of p-Nitrophenyl Acetate
  作者：Satish K. Pejaver、Robert E. Notari

  DOI：10.1002/jps.2600741107

  日期：1985.11

  the liposomal phases. Increasing the pH produced an increase in ester clearance values due to the stearylamine-containing liposomal phase, which is consistent with the formation of free amine, providing increased aminolysis. Although amide formation was also observed in stearylamine suspensions, the rate of p-nitrophenyl acetate loss was much greater in liposomal suspensions. Accelerated loss in the

  该研究的目的是确定先前报道的在带正电荷的脂质体存在下乙酸对硝基苯酯水解为对硝基苯酚的速率增加的原因。当这种电荷归因于硬脂胺的掺入时，相对于对照缓冲液，损失速率增加了5到10倍。这种速率的提高伴随着N-硬脂基乙酰胺的形成，这是以前没有考虑过的事件。用L-α-或二肉豆蔻酰基磷脂酰胆碱可获得相似的结果。但是，当脂质体上的正电荷由西曲铵离子赋予时，加速度被速率降低和不存在酰胺形成所取代。从脂质体中分离连续相提供了在动力学上与对照缓冲液等效的培养基，表明速率的提高和降低均归因于脂质体相。由于含硬脂胺的脂质体相，pH值的增加会导致酯清除率值的增加，这与游离胺的形成相一致，从而增加了氨解作用。尽管在硬脂胺悬浮液中也观察到酰胺的形成，但脂质体悬浮液中对硝基苯基乙酸酯的损失速率要大得多。在带正电荷的脂质体存在下加速损失是由于与硬脂胺反应形成了N-硬脂基乙酰胺，而不是由于正电荷，这一假设被使用含有乙tri离子