2-aminoethyl n-tetradecyl ether | 15930-69-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-aminoethyl n-tetradecyl ether
• 英文别名: 2-(Tetradecyloxy)Ethanamine；2-tetradecoxyethanamine
• CAS: 15930-69-5
• 化学式: C₁₆H₃₅NO
• 分子量: 257.46
• InChiKey: VDKIKEMSODDARD-UHFFFAOYSA-N

物化性质

• 沸点：
  347.1±15.0 °C(Predicted)
• 密度：
  0.850±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  18
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-aminoethyl n-tetradecyl ether 在 sodium hydroxide 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 80.0h， 生成 N,N-di[2-n-tetradecyloxyethyl]-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：

  溴代十四烷 在 咪唑 、 sodium azide 、 四溴化碳 、 水 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 生成 2-aminoethyl n-tetradecyl ether
  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

文献信息

• Lubricating oil compositions and concentrates and the use thereof
  申请人：ETHYL PETROLEUM ADDITIVES, INC.

  公开号：EP0492934A1

  公开（公告）日：1992-07-01

  Oleaginous compositions and additive concentrates therefor having enhanced performance characteristics comprise at least a) one or more oil-soluble overbased alkali or alkaline earth metal-containing detergents having a TBN of at least 200; and b) one or more oil-soluble additive compositions formed by heating concurrently or in any sequence at least one ashless dispersant which contains basic nitrogen and/or at least one hydroxyl group with (i) at least one inorganic phosphorus acid or anhydride, or at least one partial or total sulfur analog thereof, or any combination of the foregoing; or (ii) at least one water-hydrolyzable organic phosphorus-containing compounds and water; and (iii) at least one boron compound; such that a liquid composition containing both phosphorus and boron is formed. The weight ratio of metal as component a) to phosphorus as component b) is in the range of 0.15:1 to 10:1.

  具有增强性能特征的油性组合物及其添加剂浓缩物至少包括 a) 一种或多种油溶性过基碱金属或碱土金属洗涤剂，其 TBN 至少为 200；(b) 一种或多种油溶性添加剂组合物，通过同时或任意顺序加热至少一种无 灰分散剂而形成，该分散剂含有碱性氮和/或至少一个羟基与 (i) 至少一种无机磷酸或磷酸酐，或至少一种其部分或全部硫类似物， 或上述物质的任意组合；或 (ii) 至少一种可水解的有机含磷化合物和水；以及 (iii) 至少一种硼化合物；从而形成一种既含磷又含硼的液体组合物。作为 a)组分的金属与作为 b)组分的磷的重量比范围为 0.15:1 至 10:1。
• Lubricating oil compositions, concentrates and the use thereof
  申请人：ETHYL PETROLEUM ADDITIVES, INC.

  公开号：EP0493928A1

  公开（公告）日：1992-07-08

  Oleaginous compositions and additive concentrates therefor having enhanced performance characteristics comprise at least a) one or more oil-soluble metal dihydrocarbyl dithiophosphates or dithiocarbamates; and b) one or more oil-soluble additive compositions formed by heating concurrently or in any sequence at least one ashless dispersant which contains basic nitrogen and/or at least one hydroxyl group with (i) at least one inorganic phosphorus acid or anhydride, or at least one partial or total sulfur analog thereof, or any combination of the foregoing; or (ii) at least one water-hydrolyzable organic phosphorus compound and water; and (iii) at least one boron compound; such that a phosphorus- and boron-containing liquid composition is formed, and from which excessive water, if present, has been removed at least during or after heating with (ii), if used.

  具有增强性能特征的油胶组合物及其添加剂浓缩物至少包括 a) 一种或多种油溶性金属二氢羰基二硫代磷酸酯或二硫代氨基甲酸酯；(b) 一种或多种油溶性添加剂组合物，通过同时或任意顺序加热至少一种无 灰分散剂而形成，该分散剂含有碱性氮和/或至少一个羟基与 (i) 至少一种无机磷酸或磷酸酐，或至少一种其部分或全部硫类似物， 或上述物质的任意组合；或 (ii) 至少一种可水解的有机磷化合物和水；以及 (iii) 至少一种硼化合物；这样就形成了一种含磷和硼的液体组合物，如果使用了(ii)，在加热过程中或加热后，过量的水分（如果存在）已被去除。
• Oil additive concentrates and lubricants of enhanced performance capabilities
  申请人：ETHYL PETROLEUM ADDITIVES, INC.

  公开号：EP0531000A1

  公开（公告）日：1993-03-10

  Additive concentrates and lubricant compositions containing a combination of additives which result in enhanced performance particularly as regards extreme pressure and antiwear performance. The combination of additives so utilized comprise a-1) at least one oil-soluble additive composition formed by heating concurrently or in any sequence at least one ashless dispersant which contains basic nitrogen and/or at least one hydroxyl group with (i) at least one inorganic phosphorus acid or anhydride, or at least one partial or total sulfur analog thereof, or any combination of the foregoing, and (ii) at least one boron compound; such that a liquid composition is formed; or a-2) at least one oil-soluble boron-free additive composition formed by heating (i) at least one boron-free oil-soluble ashless dispersant containing basic nitrogen and/or at least one hydroxyl group, with (ii) at least one inorganic phosphorus acid such that a liquid boron-free phosphorus-containing composition is formed; or a-3) one or more oil-soluble additive compositions formed by heating concurrently or in any sequence at least one ashless dispersant which contains basic nitrogen and/or at least one hydroxyl group with (i) at least one water-hydrolyzable organic phosphorus compound and water; and (ii) at least one boron compound; such that a liquid phosphorus- and boron-containing composition is formed; or a-4) one or more oil-soluble boron-free additive compositions formed by heating concurrently or in any sequence (i) at least one boron-free oil-soluble ashless dispersant which contains basic nitrogen and/or at least one hydroxyl group, with (ii) -at least one water-hydrolyzable organic phosphorus compound and water; such that a liquid boron-free phosphorus-containing composition is formed; and b) at least one oil-soluble metal-free sulfur-containing antiwear and/or extreme pressure agent having a sulfur content of at least 20% by weight; components a-1), a-2), a-3) or a-4) and b) being proportioned such that the mass ratio (wt:wt) of sulfur in component b) to phosphorus in component a-1), a-2), a-3) or a-4) is in the range of 8:1 to 30:1.

  添加剂浓缩物和润滑剂组合物含有添加剂组合，可提高性能，特别是在极压和抗磨损性能方面。添加剂组合包括 a-1) 至少一种油溶性添加剂组合物，通过同时或任意顺序加热至少一种含碱式氮和/或至少一个羟基的无灰分散剂与(i) 至少一种无机磷酸或磷酸酐，或至少一种其部分或全部硫类似物，或上述物质的任意组合，以及(ii) 至少一种硼化合物，从而形成液体组合物；或 a-2) 至少一种油溶性无硼添加剂组合物，通过加热 (i) 至少一种含碱式氮和/或至少一个羟基的无硼油溶性无灰分散剂，与 (ii) 至少一种无机磷酸，从而形成液态无硼含磷组合物；或 a-3) 一种或多种油溶性添加剂组合物，通过同时或任意顺序加热至少一种含 碱式氮和/或至少一个羟基的无灰分散剂与(i)至少一种可水解的有机磷化 合物和水；和(ii) 至少一种硼化合物；从而形成一种液态含磷和硼的组合物；或 a-4) 一种或多种油溶性无硼添加剂组合物，通过同时或任意顺序加热(i) 至少一种含碱性氮和/或至少一种羟基的无硼油溶性无灰分散剂与(ii) 至少一种可水解的有机磷化合物和水；从而形成一种液态无硼含磷组合物；及 b) 至少一种油溶性无金属含硫抗磨剂和/或极压剂，其硫含量至少为 20%（重量比）；组分 a-1)、a-2)、a-3)或 a-4) 和 b) 的比例为：组分 b) 中硫与组分 a-1)、a-2)、a-3)或 a-4) 中磷的质量比（重量比）在 8:1 至 30:1 之间。
• COMB-SHAPED DIOL, WATER-SOLUBLE POLYURETHANE, AND USE THEREOF
  申请人：Mitsui Chemicals, Inc.

  公开号：EP1184364B1

  公开（公告）日：2010-07-28
• Oil-soluble phosphorus antiwear additives for lubricants
  申请人：ETHYL PETROLEUM ADDITIVES, INC.

  公开号：EP0359522B1

  公开（公告）日：1992-06-24