N¹,N⁷-bis(trifluoroacetyl)diethylenetriamine trifluoacetate

• 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
• 英文名称: N¹,N⁷-bis(trifluoroacetyl)diethylenetriamine trifluoacetate
• 英文别名: 2,2,2-trifluoroacetic acid; 2,2,2-trifluoro-N-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethylamino]ethyl]acetamide；2,2,2-trifluoroacetic acid;2,2,2-trifluoro-N-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethylamino]ethyl]acetamide
• 化学式: C₂HF₃O₂*C₈H₁₁F₆N₃O₂
• 分子量: 409.209
• InChiKey: WUEPMEXUMQVEGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.57
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 N¹,N⁷-bis(trifluoroacetyl)diethylenetriamine trifluoacetate 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到bis{2-[(2,2,2-trifluoroacetyl)amino]ethyl}carbamic acid tert-butyl ester
  参考文献：
  名称：

  Lipophilic Pyrylium Salts in the Synthesis of Efficient Pyridinium-Based Cationic Lipids, Gemini Surfactants, and Lipophilic Oligomers for Gene Delivery

  摘要：

  Several new classes of pyridinium cationic lipids were synthesized and tested as gene delivery agents. They were obtained through a procedure that generates simultaneously the heterocyclic ring and the positively charged nitrogen atom, using lipophilic pyrylium salts as key intermediates that react with primary amines, yielding pyridinium salts. The choice of the appropriately substituted primary amine, diamine or polyamine, allows the design of the shape of the final lipids, gemini surfactants, or lipophilic polycations. We report also a comprehensive structure-activity relationship study that identified the most efficient structural variables at the levels of the hydrophobic anchor, linker, and counterion for these classes of pyridinium cationic lipids. This study was also aimed at finding the best liposomal formulation for the new transfection agents.

  DOI：

  10.1021/jm0601755
• 作为产物：
  描述：

  三氟乙酸乙酯 、 二乙烯三胺 在 水 作用下， 以 乙腈 为溶剂， 以91%的产率得到N¹,N⁷-bis(trifluoroacetyl)diethylenetriamine trifluoacetate
  参考文献：
  名称：

  多胺伯氨基选择性三氟乙酰化的一步法

  摘要：

  多胺与三氟乙酸乙酯在湿乙腈中的反应导致伯氨基的选择性三氟乙酰化。已表明该反应适用于多种多胺。

  DOI：

  10.1016/0040-4039(95)00630-u

文献信息

• A one-step procedure for the selective trifluoroacetylation of primary amino groups of polyamines
  作者：Mary C. O'Sullivan、Damon M. Dalrymple

  DOI：10.1016/0040-4039(95)00630-u

  日期：1995.5

  The reaction of polyamines with ethyl trifluoroacetate in wet acetonitrile results in the selective trifluoroacetylation of primary amino groups. This reaction is shown to be applicable to a range of polyamines.

  多胺与三氟乙酸乙酯在湿乙腈中的反应导致伯氨基的选择性三氟乙酰化。已表明该反应适用于多种多胺。
• Phosphonolipids as non-viral vectors for gene therapy
  作者：Virginie Floch、Gwénaëlle Le Bolc'h、Christine Gable-Guillaume、Nathalie Le Bris、Jean-Jacques Yaouanc、Hervé des Abbayes、Claude Férec、Jean-Claude Clément

  DOI：10.1016/s0223-5234(99)80017-8

  日期：1998.12

  Several phosphonates with two fatty chains and different polar heads were synthesized and evaluated for their potential to transfer DNA into epithelial (COS-7) and hematopoietic (K562) cell lines, and compared to commercially available references. In both cases, ammonium-phosphonates were particularly efficient. (C) Elsevier, Paris.
• Lipophilic Pyrylium Salts in the Synthesis of Efficient Pyridinium-Based Cationic Lipids, Gemini Surfactants, and Lipophilic Oligomers for Gene Delivery
  作者：Marc Antoniu Ilies、William A. Seitz、Betty H. Johnson、Edward L. Ezell、Aaron L. Miller、E. Brad Thompson、Alexandru T. Balaban

  DOI：10.1021/jm0601755

  日期：2006.6.1

  Several new classes of pyridinium cationic lipids were synthesized and tested as gene delivery agents. They were obtained through a procedure that generates simultaneously the heterocyclic ring and the positively charged nitrogen atom, using lipophilic pyrylium salts as key intermediates that react with primary amines, yielding pyridinium salts. The choice of the appropriately substituted primary amine, diamine or polyamine, allows the design of the shape of the final lipids, gemini surfactants, or lipophilic polycations. We report also a comprehensive structure-activity relationship study that identified the most efficient structural variables at the levels of the hydrophobic anchor, linker, and counterion for these classes of pyridinium cationic lipids. This study was also aimed at finding the best liposomal formulation for the new transfection agents.