1-(2-溴乙氧基)十二烷 | 22732-79-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-溴乙氧基)十二烷
• 英文名称: 2-bromoethyl n-dodecyl ether
• 英文别名: 1-(2-bromoethoxy)dodecane；2-dodecyloxyethyl bromide；(2-bromo-ethyl)-dodecyl ether；(2-Brom-aethyl)-dodecyl-aether；1-Brom-2-dodecyloxy-aethan
• CAS: 22732-79-2
• 化学式: C₁₄H₂₉BrO
• 分子量: 293.288
• InChiKey: FCLPYIDOXPMKQR-UHFFFAOYSA-N

物化性质

• 沸点：
  132-133 °C(Press: 1 Torr)
• 密度：
  1.0418 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  16
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-溴乙氧基)十二烷 在 sodium azide 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 2-(dodecyloxy)ethanamine
  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：

  乙二醇单十二烷基醚 在 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(2-溴乙氧基)十二烷
  参考文献：
  名称：

  芳环对合成杂环表面活性剂表面和自组装性能的影响

  摘要：

  杂环基阳离子表面活性剂，其十二烷基尾基通过芳族醚 [3-(4-十二烷氧基苄基)-1-甲基-溴化咪唑鎓 ( Ar-I ) 和 4-(4-十二烷氧基苄基)-4-甲基桥接至头基-溴化吗啉( Ar-M )]或通过脂肪族醚[3-(2-十二烷氧基乙基)-1-甲基溴化咪唑鎓( Al-I )和4-(2-十二烷氧基乙基)-4-甲基溴化吗啉( Al-M) )] 使用不同的光谱技术进行合成和表征。为了合成Ar-I和Ar-M，首先将4-羟基苯甲酸酯化，然后进行O-烷基化、还原、溴化，最后用1-甲基咪唑或4-甲基吗啉季铵化。为了合成脂肪族类似物（A1-I和A1-M），乙二醇首先被烷基化，然后用1-甲基咪唑或4-甲基吗啉进行甲苯磺化、溴化和季铵化。评估合成表面活性剂的表面和自组装性能。研究了桥接表面活性剂极性头和非极性尾部的苯环的存在或不存在以及头基区域中杂环部分的类型对胶束化和表面性质（例如润湿、发泡和乳化）的影响

  DOI：

  10.1002/jsde.12711

文献信息

• Synthesis of some acyclic quaternary ammonium compounds. Alkylation of secondary and tertiary amines in a two-phase system
  作者：A. V. Kharlamov、O. I. Artyushin、N. A. Bondarenko

  DOI：10.1007/s11172-014-0761-x

  日期：2014.11

  and asymmetrical quaternary ammonium chlorides of the general formula R1R2R3N+AR4Cl– (R1 = Me, Bu; R2 = n-C12H25, PhCH2, CnH2n+1(OCH2CH2)m, n = 9 and 12, m = 1 and 2; R3 = n-C12H25, PhCH2, HOCH2CH2,–OOCCH2; R4 = n-C12H25, PhCH2; A = (CH2CH2O)1,2, CH2C(O)O) was synthesized by the alkylation of tertiary amines in a two-phase system containing water. A convenient method for the synthesis of the initial

  通式R1R2R3N+AR4Cl–（R1 = Me, Bu; R2 = n-C12H25, PhCH2, CnH2n+1(OCH2CH2)m, n = 9 and 12, m = 1）的一系列无环对称和不对称季铵氯化物和 2; R3 = n-C12H25, PhCH2, HOCH2CH2,–OOCCH2; R4 = n-C12H25, PhCH2; A = (CH2CH2O)1,2, CH2C(O)O) 是通过叔胺的烷基化合成的相系统含水。一种合成通式 MeNR1R2 的初始对称和不对称叔胺的简便方法（R1 = Me, Bu；R2 = n-C12H25, PhCH2, CnH2n+1(OCH2CH2)m, n = 9 和 12, m = 1 和 2) 在有机相-水相非均相系统中被开发出来，它允许使用碱和胺的水溶液。
• [EN] IONIZABLE LIPIDS FOR NUCLEIC ACID DELIVERY<br/>[FR] LIPIDES IONISABLES POUR L'ADMINISTRATION D'ACIDES NUCLÉIQUES
  申请人：PREC NANOSYSTEMS INC

  公开号：WO2021000041A1

  公开（公告）日：2021-01-07

  The present document describes compounds, or pharmaceutically acceptable salt thereof, of a core formula (I) Wherein R1 includes an amino group. These compounds are particularly useful in the formulation and in vivo and ex vivo delivery of nucleic acid and protein therapeutics for preparing and implementing T cell transfection, gene editing, cancer therapies, cancer prophylactics, and in the preparation of vaccines.

  本文件描述了核心公式（I）的化合物或其药用可接受盐，其中R1包括氨基团。这些化合物在核酸和蛋白治疗剂的制剂、体内和体外递送中特别有用，用于制备和实施T细胞转染、基因编辑、癌症治疗、癌症预防以及疫苗的制备。
• Weber, Edwin, Liebigs Annalen der Chemie, 1983, # 5, p. 770 - 801
  作者：Weber, Edwin

  DOI：——

  日期：——
• 91. Antituberculous compounds. Part VI. p-(ω-Alkoxyalkoxy)-N-arylbenzamidines and analogues
  作者：F. C. Cooper、M. W. Partridge

  DOI：10.1039/jr9500000459

  日期：——
• SMITH, KIM R.;BORLAND, JAMES E.;SAUER, JOE D.
  作者：SMITH, KIM R.、BORLAND, JAMES E.、SAUER, JOE D.

  DOI：——

  日期：——