(2E,4E)-N-(2-Azidoethyl)-2,4-hexadienamide | 1253641-78-9

• 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: (2E,4E)-N-(2-Azidoethyl)-2,4-hexadienamide
• 英文别名: (2E,4E)-N-(2-azidoethyl)hexa-2,4-dienamide
• CAS: 1253641-78-9
• 化学式: C₈H₁₂N₄O
• 分子量: 180.209
• InChiKey: LTAWUFZEYPSJBK-MQQKCMAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  PPC-C32-PPC 、 (2E,4E)-N-(2-Azidoethyl)-2,4-hexadienamide 在 copper(II) acetate monohydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 dotriacontane-1,32-diyl bis(2-(((1-(2-((2E,4E)-hexa-2,4-dienamido)ethyl)-1H-1,2,3-triazol-4-yl)methyl)dimethylammonio)ethyl) bis(phosphate)
  参考文献：
  名称：

  Amino-functionalized single-chain bolalipids: Synthesis and aggregation behavior of new basic building blocks

  摘要：

  Herein, we report the synthesis of two novel, amino-functionalized single-chain bolalipids and, based on those, a general synthetic approach for the insertion of various carboxylic acids into the bolalipid headgroups, e.g. alpha-lipoic acid for one-dimensional fixation of gold nanoparticles, sorbic acid for polymerization experiments, or lysine for the use in gene delivery systems. The temperature- and pH-dependent self-assembly of amino-functionalized bolalipids into nanofibers and micelles was investigated by differential scanning calorimetry (DSC), transmission electron microscopy (TEM) and dynamic light scattering (DLS). Rheological measurements were used to describe the macroscopic behavior of the formed temperature switchable hydrogels that can be fine-tuned for drug delivery applications. We showed that the viscoelastic properties of the hydrogel strongly depend on ionic interactions between bolalipid headgroups as well as on the ability to form hydrogen bonds. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bpc.2010.01.013
• 作为产物：
  描述：

  山梨酸 、 2-叠氮基乙胺 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2E,4E)-N-(2-Azidoethyl)-2,4-hexadienamide
  参考文献：
  名称：

  Amino-functionalized single-chain bolalipids: Synthesis and aggregation behavior of new basic building blocks

  摘要：

  Herein, we report the synthesis of two novel, amino-functionalized single-chain bolalipids and, based on those, a general synthetic approach for the insertion of various carboxylic acids into the bolalipid headgroups, e.g. alpha-lipoic acid for one-dimensional fixation of gold nanoparticles, sorbic acid for polymerization experiments, or lysine for the use in gene delivery systems. The temperature- and pH-dependent self-assembly of amino-functionalized bolalipids into nanofibers and micelles was investigated by differential scanning calorimetry (DSC), transmission electron microscopy (TEM) and dynamic light scattering (DLS). Rheological measurements were used to describe the macroscopic behavior of the formed temperature switchable hydrogels that can be fine-tuned for drug delivery applications. We showed that the viscoelastic properties of the hydrogel strongly depend on ionic interactions between bolalipid headgroups as well as on the ability to form hydrogen bonds. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bpc.2010.01.013

文献信息

• Amino-functionalized single-chain bolalipids: Synthesis and aggregation behavior of new basic building blocks
  作者：Simon Drescher、Gesche Graf、Gerd Hause、Bodo Dobner、Annette Meister

  DOI：10.1016/j.bpc.2010.01.013

  日期：2010.8

  Herein, we report the synthesis of two novel, amino-functionalized single-chain bolalipids and, based on those, a general synthetic approach for the insertion of various carboxylic acids into the bolalipid headgroups, e.g. alpha-lipoic acid for one-dimensional fixation of gold nanoparticles, sorbic acid for polymerization experiments, or lysine for the use in gene delivery systems. The temperature- and pH-dependent self-assembly of amino-functionalized bolalipids into nanofibers and micelles was investigated by differential scanning calorimetry (DSC), transmission electron microscopy (TEM) and dynamic light scattering (DLS). Rheological measurements were used to describe the macroscopic behavior of the formed temperature switchable hydrogels that can be fine-tuned for drug delivery applications. We showed that the viscoelastic properties of the hydrogel strongly depend on ionic interactions between bolalipid headgroups as well as on the ability to form hydrogen bonds. (C) 2010 Elsevier B.V. All rights reserved.