bis(2-(dodecyloxy)ethyl)amine | 64062-82-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: bis(2-(dodecyloxy)ethyl)amine
• 英文别名: Bis-(2-lauroxyethyl)amine；2-dodecoxy-N-(2-dodecoxyethyl)ethanamine
• CAS: 64062-82-4
• 化学式: C₂₈H₅₉NO₂
• 分子量: 441.782
• InChiKey: ORNLQJOQYNLYMU-UHFFFAOYSA-N

物化性质

• 沸点：
  508.7±25.0 °C(Predicted)
• 密度：
  0.862±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  31
• 可旋转键数：
  28
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis(2-(dodecyloxy)ethyl)amine 、 2-氯乙醇 在 sodium hydroxide 作用下， 反应 38.0h， 以98.4 mg的产率得到N,N-di[2-n-dodecyloxyethyl]-N,N-di[2-hydroxyethyl]ammonium chloride
  参考文献：
  名称：

  Anchor Dependency for Non-Glycerol Based Cationic Lipofectins: Mixed Bag of Regular and Anomalous Transfection Profiles

  摘要：

  Although detailed structure activity, physicochemical and biophysical investigations in probing the anchor influence in liposomal gene delivery have been reported for glycerol-based transfection lipids, the corresponding investigation for non-glycerol based simple monocationic transfection lipids have not yet been undertaken. Towards this end, herein, we delineate our structure - activity and physicochemical approach in deciphering the anchor dependency in liposomal gene delivery using fifteen new structural analogues (lipids 1 - 15) of recently reported nonglycerol based monocationic transfection lipids. The C-14 analogues in both series 1 (lipids 1 - 6) and series 2 (lipids 7-15) showed maximum efficiency in transfecting COS-1 and CHO cells. However, the C-12 analogue of the ether series (lipid 3) exhibited a seemingly anomalous behavior compared with its transfection efficient C-10 and C-14 analogues (lipids 2 and 4) in being completely inefficient to transfect both COS-1 and CHO cells. The present structure - activity investigation also convincingly demonstrates that enhancement of transfection efficiencies through incorporation of membrane reorganizing unsaturation elements in the hydrophobic anchor of cationic lipids is not universal but cell dependent. The strength of the interaction of lipids 1 - 15 with DNA was assessed by their ability to exclude ethidium bromide bound to the DNA. Cationic lipids with long hydrophobic tails were found, in general, to be efficient in excluding EtBr from DNA. Gel to liquid crystalline transition temperatures of the lipids was measured by fluorescence anisotropy measurement technique. In general (lipid 2 being an exception), transfection efficient lipids were found to have their mid transition temperatures at or below physiological temperatures (37degreesC).

  DOI：

  10.1002/1521-3765(20020215)8:4<900::aid-chem900>3.0.co;2-x
• 作为产物：
  描述：

  甲烷磺酸十二烷基酯 在 10 wt% Pd(OH)2 on carbon 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 24.17h， 生成 bis(2-(dodecyloxy)ethyl)amine
  参考文献：
  名称：

  二乙醇胺合成对称低聚乙二醇化仲胺

  摘要：

  含有对称仲胺的单分散低聚乙二醇 (M-OEG) 是药物开发和材料科学中非常有价值的合成中间体。本文描述了具有柔性 M-OEG 和/或烷基链的 M-OEG 仲胺的可扩展三步合成。通过二乙醇胺的还原胺化、威廉姆森醚合成和随后的脱保护，方便地制备了一系列化学结构多样且可微调的M-OEGs仲胺。所提出的策略具有易于获得的起始材料、简单的催化系统、可扩展的合成以及避免使用爆炸性叠氮化钠的吸引力。

  DOI：

  10.1039/d2ob00605g

文献信息

• 含醚键的仲胺、酰胺荚醚配体及其制备方法与 应用
  申请人：四川大学

  公开号：CN111875512B

  公开（公告）日：2021-09-14

  本发明公开了一种含醚键的仲胺、酰胺荚醚配体及其制备方法与应用，该含醚键的仲胺，其结构通式为本发明所提供的仲胺含有醚键，具有比单纯碳链仲胺更大的柔性，且易于延长原子个数，从而为有机合成化学和药物化学领域提供了具有优异性能的候选仲胺。以仲胺为原料制备的酰胺荚醚配体在乏燃料后处理中，将其作为镧系/锕系共萃体系的萃取剂，能够在更高的金属离子浓度或硝酸浓度下有效抑制三相的形成，因此在工业应用的酸度范围内实现良好的分离效果，因而不仅具有较强的实用性，且在先进核燃料循环领域也具有很好的应用前景。
• Synthesis of Secondary Amines with Long Chains Containing Ether Bonds
  作者：Songdong Ding、Haowei Xu、Xiuying Yang、Lianjun Song、Xueyu Wang、Qiuju Li、Lanlan He

  DOI：10.1055/s-0040-1719921

  日期：2022.7

  secondary amines with long chains containing ether bonds were synthesized by a three-step protection–etherification–deprotection process from diethanolamine. The optimum reaction conditions were examined. This method has the advantages of simplicity, low cost, and high yield. Furthermore, some new downstream products (diglycolamides) were prepared from the ether-containing long-chain secondary amines as reactants

  通过二乙醇胺的三步保护-醚化-去保护过程合成了一类新型的含有醚键的长链仲胺。考察了最佳反应条件。该方法具有简单、成本低、收率高等优点。此外，以含醚的长链仲胺为反应物，制备了一些新的下游产品（二甘醇酰胺），并评估了它们在萃取几种金属离子中的负载能力。
• US4556630A
  申请人：——

  公开号：US4556630A

  公开（公告）日：1985-12-03