3-N,N-Dihexadecanylaminopropan-1-ol | 88090-04-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-N,N-Dihexadecanylaminopropan-1-ol
• 英文别名: 3-(Dihexadecylamino)-1-propanol；3-(Dihexadecylamino)propan-1-OL
• CAS: 88090-04-4
• 化学式: C₃₅H₇₃NO
• 分子量: 523.971
• InChiKey: OQXSWCAMQSWLOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.4
• 重原子数：
  37
• 可旋转键数：
  33
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-N,N-Dihexadecanylaminopropan-1-ol 在 氯化亚砜 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 26.0h， 生成 N,N-Dihexadecyl-1H-imidazole-1-propanamine
  参考文献：
  名称：

  含咪唑和吡唑配体的表面活性剂的聚集行为和铜结合性能

  摘要：

  描述了简单的二烷基胺-咪唑和二烷基胺-吡唑表面活性剂的合成和聚集行为。在一当量的HCl存在下，咪唑表面活性剂形成稳定的囊状分散体。向这些分散体中添加二氯化铜（II）导致形成金属囊泡，其中四个咪唑基团与一个铜（II）离子配位。这些金属囊泡是不稳定的，并缓慢地转变成堆叠的双层，其沉淀。另一方面，吡唑表面活性剂不形成囊泡，但以一摩尔当量的HCl给出不溶于水的堆叠双层。这些堆叠的双层中的吡唑部分不配位铜（II）离子。此行为很可能是由于在单质子化吡唑表面活性剂分子中形成了分子内氢键。

  DOI：

  10.1002/recl.19941130405
• 作为产物：
  描述：

  双十六烷基胺 在 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 3-N,N-Dihexadecanylaminopropan-1-ol
  参考文献：
  名称：

  Distance of Hydroxyl Functionality from the Quaternized Center Influence DNA Binding and in Vitro Gene Delivery Efficacies of Cationic Lipids with Hydroxyalkyl Headgroups

  摘要：

  In vitro gene delivery efficacies of cationic amphiphiles 1-7 (Scheme 1) were measured by both the reporter gene expression assays in CHO, COS-1, HepG2, and MCF7 cells and by the whole cell histochemical X-gal staining of representative Chinese hamster ovary cells. Our results demonstrated that in vitro gene delivery efficiencies of cationic lipids with hydroxyalkyl headgroups are adversely affected by increased covalent distances between the hydroxyl functionality and the cationic centers. Findings in the DNase I protection experiments and transmission electron microscopic study support the notion that such compromised gene delivery efficacies may originate from poor lipid-DNA binding interactions and significantly increased lipoplex nanosizes.

  DOI：

  10.1021/jm049656j

文献信息

• Schade, W.; Beger, J.; Jacobi, R., Journal fur praktische Chemie (Leipzig 1954), 1983, vol. 325, # 3, p. 364 - 374
  作者：Schade, W.、Beger, J.、Jacobi, R.、Neumann, R.

  DOI：——

  日期：——
• SCHADE, W.;BEGER, J.;JACOBI, R.;NEUMANN, R., J. PRAKT. CHEM., 1983, 325, N 3, 364-374
  作者：SCHADE, W.、BEGER, J.、JACOBI, R.、NEUMANN, R.

  DOI：——

  日期：——
• Distance of Hydroxyl Functionality from the Quaternized Center Influence DNA Binding and in Vitro Gene Delivery Efficacies of Cationic Lipids with Hydroxyalkyl Headgroups
  作者：Yenugonda Venkata Mahidhar、Mukthavaram Rajesh、Sunkara Sakunthala Madhavendra、Arabinda Chaudhuri

  DOI：10.1021/jm049656j

  日期：2004.11.1

  In vitro gene delivery efficacies of cationic amphiphiles 1-7 (Scheme 1) were measured by both the reporter gene expression assays in CHO, COS-1, HepG2, and MCF7 cells and by the whole cell histochemical X-gal staining of representative Chinese hamster ovary cells. Our results demonstrated that in vitro gene delivery efficiencies of cationic lipids with hydroxyalkyl headgroups are adversely affected by increased covalent distances between the hydroxyl functionality and the cationic centers. Findings in the DNase I protection experiments and transmission electron microscopic study support the notion that such compromised gene delivery efficacies may originate from poor lipid-DNA binding interactions and significantly increased lipoplex nanosizes.
• Aggregation behaviour and copper-binding properties of surfactants containing imidazole and pyrazole ligands
  作者：J.H. van Esch、M. Damen、M.C. Feiters、R.J.M. Nolte

  DOI：10.1002/recl.19941130405

  日期：——

  precipitate. The pyrazole surfactants on the other hand do not form vesicles but give, with one molar equivalent of HCl, water-insoluble stacked bilayers. The pyrazole moieties in these stacked bilayers do not coordinate copper(II) ions. This behaviour is most probably due to the formation of an intramolecular hydrogen bond in the mono-protonated pyrazole surfactant molecule. The imidazole surfactants cannot

  描述了简单的二烷基胺-咪唑和二烷基胺-吡唑表面活性剂的合成和聚集行为。在一当量的HCl存在下，咪唑表面活性剂形成稳定的囊状分散体。向这些分散体中添加二氯化铜（II）导致形成金属囊泡，其中四个咪唑基团与一个铜（II）离子配位。这些金属囊泡是不稳定的，并缓慢地转变成堆叠的双层，其沉淀。另一方面，吡唑表面活性剂不形成囊泡，但以一摩尔当量的HCl给出不溶于水的堆叠双层。这些堆叠的双层中的吡唑部分不配位铜（II）离子。此行为很可能是由于在单质子化吡唑表面活性剂分子中形成了分子内氢键。