N-(2-aminoethyl)oleamide | 10375-09-4

• 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-(2-aminoethyl)oleamide
• 英文别名: Aminoethyloleylamide；(Z)-N-(2-aminoethyl)octadec-9-enamide
• CAS: 10375-09-4
• 化学式: C₂₀H₄₀N₂O
• 分子量: 324.55
• InChiKey: NEAVWSTWAPWAPP-KTKRTIGZSA-N

物化性质

• 沸点：
  487.8±38.0 °C(Predicted)
• 密度：
  0.896±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  23
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-aminoethyl)oleamide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 C₂₁H₄₂N₄O*C₂HF₃O₂
  参考文献：
  名称：

  Design and Synthesis of Lipids for the Fabrication of Functional Lipidic Cubic-Phase Biomaterials

  摘要：

  A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of alpha-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.

  DOI：

  10.1021/jo301659c
• 作为产物：
  描述：

  油酰氯 在 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 N-(2-aminoethyl)oleamide
  参考文献：
  名称：

  Design and Synthesis of Lipids for the Fabrication of Functional Lipidic Cubic-Phase Biomaterials

  摘要：

  A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of alpha-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.

  DOI：

  10.1021/jo301659c

文献信息

• ANIONIC-CATIONIC-NONIONIC SURFACTANT,PRODUCTION AND USE THEREOF
  申请人：CHINA PETROLEUM & CHEMICAL CORPORATION

  公开号：US20170313928A1

  公开（公告）日：2017-11-02

  This invention relates to an anionic-cationic-nonionic surfactant as substantially represented by the formula (I), production and use thereof in tertiary oil recovery. The anionic-cationic-nonionic surfactant of this invention exhibits significantly improved interfacial activity and stability as compared with the prior art. With the present anionic-cationic-nonionic surfactant, a flooding fluid composition for tertiary oil recovery with improved oil displacement efficiency and oil washing capability as compared with the prior art could be produced. In the formula (I), each group is as defined in the specification.

  这项发明涉及一种阴离子-阳离子-非离子表面活性剂，其大致由式(I)所代表，以及该表面活性剂在三次采油中的生产和使用。该发明的阴离子-阳离子-非离子表面活性剂与现有技术相比具有明显改善的界面活性和稳定性。采用这种阴离子-阳离子-非离子表面活性剂，可以制备出用于三次采油的注水液组成物，其具有比现有技术更高的油位移效率和油洗能力。在式(I)中，每个基团如规范中所定义。
• Synthesis and biological evaluation of a new series of N -acyldiamines as potential antibacterial and antifungal agents
  作者：Bianca da S. Ferreira、Angelina M. de Almeida、Thiago C. Nascimento、Pedro P. de Castro、Vania L. Silva、Claúdio G. Diniz、Mireille Le Hyaric

  DOI：10.1016/j.bmcl.2014.08.047

  日期：2014.10

  In continuation of our efforts to find new antimicrobial compounds, series of fatty N-acyldiamines were prepared from fatty methyl esters and 1,2-ethylenediamine, 1,3-propanediamine or 1,4-butanediamine. The synthesized compounds were screened for their antibacterial activity against Gram-positive bacteria (Staphylococcus aureus, Staphylococcus epidermidis), Gram-negative bacteria (Escherichia coli

  为了继续努力寻找新的抗菌化合物，从脂肪甲酯和1,2-乙二胺，1,3-丙二胺或1,4-丁二胺制备了一系列的脂肪N-酰基二胺。筛选合成的化合物对革兰氏阳性菌（金黄色葡萄球菌，表皮葡萄球菌），革兰氏阴性菌（大肠杆菌，铜绿假单胞菌）的抗菌活性以及对四种念珠菌（C. albicans，C.热带，光滑念珠菌和近平滑念珠菌）。化合物5a（N-（2-氨基乙基）十二碳酰胺），5b（N-（2-氨基乙基）四碳酰胺）和6d（N-（3-氨基丙基）油酰胺）对革兰氏阳性细菌的活性最高，MIC值为1至16并评估其对21种耐甲氧西林金黄色葡萄球菌临床分离株的活性。所有化合物均表现出良好至中等的抗真菌活性。与氯霉素相比，化合物6b表现出相似的活性（MIC 50  = 16μg/ mL）。亲脂性和生物学活性之间可以建立正相关。
• 一种可聚合单体的制备方法和应用
  申请人：中国石油化工股份有限公司

  公开号：CN105085306B

  公开（公告）日：2017-02-15

  本发明提供一种可聚合单体的制备方法和应用，该方法包括以下步骤：(1)在缩合反应条件下，将通式为NH2‑(CH2)n‑NH2的二胺与通式为R‑COOH的羧酸接触，得到式(Ι)所示的中间体M；(2)在酰胺化反应条件下，将所述中间体M与丙烯酸接触，得到式(II)所示的可聚合单体，其中，n为2‑8的整数，R为C11‑C24的烃基。该方法获得的产物的纯度和收率较高，而且生产成本较低；将本发明提供的可聚合单体与其他单体共聚，可得到具有高分子量、高表观粘度以及优异的耐热性能和抗盐性能的驱油用聚合物，该聚合物与表面活性剂复配的驱油剂具有较高的粘度、优异的耐热性能和抗盐性能。
• LDL-based nanoparticles for contrast enhanced MRI of atheroplaques in mouse models
  作者：Yoko Yamakoshi、Hui Qiao、Andrew N. Lowell、Mark Woods、Betty Paulose、Yuka Nakao、Hualei Zhang、Ting Liu、Sissel Lund-Katz、Rong Zhou

  DOI：10.1039/c1cc10924c

  日期：——

  A LDL particle functionalized with a GdDO3A-monoamide chelate with a long alkenyl anchor (GdDO3A-OA) was prepared for in vivodetection of atheroplaques. The GdDO3A-OA, when successfully intercalated into the lipid layer of LDL particles, led to a significant enhancement of magnetic resonance imaging signal intensity of atheroplaques in atherosclerosis mouse models.

  制备了一种具有长烯基锚的 GdDO3A-单酰胺螯合物（GdDO3A-OA）功能化的低密度脂蛋白颗粒，用于活体检测动脉粥样斑块。当 GdDO3A-OA 成功插入低密度脂蛋白颗粒的脂质层后，动脉粥样硬化小鼠模型中动脉粥样斑块的磁共振成像信号强度显著增强。
• Design, Synthesis and Gelation of Low Molecular Weight Organo-Gelators Derived from Oleic Acid via Amidation
  作者：Narendra S. Joshi、Govinda P. Waghulde、Gaurav R. Gupta、Raju P. Phalak

  DOI：10.13005/ojc/370514

  日期：2021.10.30

  In recent decades, gels have been widely considered for various medicinal purposes and, in particular, wound healing applications. In this regard, amides of oleic acids and 9, 10-dihydroxyoctadecanoic acid are synthesized and characterized with the help of modern analytical tools. Among the mentioned amide frameworks, N-(2-aminoethyl)-oleamide exhibits high order of gelation not only with different organic solvents such as n-hexane and DMSO but also with different edible oils such as sesame oil, mustard oil, coconut oil and citriodora oil. Here, we briefly discuss the optimization of gelation conditions for the synthesized amides as organo-gelator, in addition to that the minimum gelation concentration and gelation temperature have also been studied.

  近几十年来，凝胶被广泛考虑用于各种医学目的，特别是在创伤愈合应用中。在这方面，通过现代分析工具合成和表征了油酸酰胺和9,10-二羟基十八碳酸的酰胺。在提到的酰胺框架中，N-(2-氨基乙基)-油酰胺不仅与不同的有机溶剂如正己烷和DMSO，而且与不同的食用油如芝麻油、芥末油、椰子油和柠檬桉油都表现出高度的凝胶化能力。在这里，我们简要讨论了合成的酰胺作为有机凝胶剂的凝胶化条件的优化，此外还研究了最小凝胶浓度和凝胶化温度。