N-(2,3-dioleyloxypropyl)phthalimide | 396727-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(2,3-dioleyloxypropyl)phthalimide
• 英文别名: 2-[2,3-bis[(Z)-octadec-9-enoxy]propyl]isoindole-1,3-dione
• CAS: 396727-94-9
• 化学式: C₄₇H₇₉NO₄
• 分子量: 722.149
• InChiKey: OAEWNAOQQHEIQW-CLFAGFIQSA-N

物化性质

• 沸点：
  747.5±60.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.5
• 重原子数：
  52
• 可旋转键数：
  37
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2,3-dioleyloxypropyl)phthalimide 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以87.5%的产率得到2,3-dioleyloxypropylamine
  参考文献：
  名称：

  Synthesis of Novel Cationic Lipids:  Effect of Structural Modification on the Efficiency of Gene Transfer

  摘要：

  A series of novel cationic lipids was designed and synthesized in an effort to understand the importance of the various structural features with respect to transfection efficiency. Particular attention has been paid to the hydrophobic domain and the cationic headgroup. An efficient method of synthesizing asymmetric diether lipids is described, using alkyl chains ranging from C-12 to C-18 and the unsaturated oleyl group. The ternary formulations including the diether lipid 3beta-[N-(N',N'-dimethylaminoethyl)carbamoyl]cholesterol (DC-Chol) and dioleoyl phosphatidylethanolamine (DOPE) were up to 10-fold more efficacious in in vitro assays than the DC-Chol/DOPE control. The shorter and most asymmetric diether lipids performed the best. The chemical nature and basicity of the headgroups have been varied by the coupling of the four naturally occurring amino acids with cationic side chains-arginine, histidine, lysine, and tryptophan. Transfection efficiency was highest for arginine/lysine derivatives, with binary formulations containing the amino acid derivative alone and,DOPE proving superior.

  DOI：

  10.1021/jm010918g
• 作为产物：
  描述：

  油醇 在 吡啶 、 1,8-双二甲氨基萘 作用下， 以 二氯甲烷 为溶剂， 反应 80.0h， 生成 N-(2,3-dioleyloxypropyl)phthalimide
  参考文献：
  名称：

  Synthesis of Novel Cationic Lipids:  Effect of Structural Modification on the Efficiency of Gene Transfer

  摘要：

  A series of novel cationic lipids was designed and synthesized in an effort to understand the importance of the various structural features with respect to transfection efficiency. Particular attention has been paid to the hydrophobic domain and the cationic headgroup. An efficient method of synthesizing asymmetric diether lipids is described, using alkyl chains ranging from C-12 to C-18 and the unsaturated oleyl group. The ternary formulations including the diether lipid 3beta-[N-(N',N'-dimethylaminoethyl)carbamoyl]cholesterol (DC-Chol) and dioleoyl phosphatidylethanolamine (DOPE) were up to 10-fold more efficacious in in vitro assays than the DC-Chol/DOPE control. The shorter and most asymmetric diether lipids performed the best. The chemical nature and basicity of the headgroups have been varied by the coupling of the four naturally occurring amino acids with cationic side chains-arginine, histidine, lysine, and tryptophan. Transfection efficiency was highest for arginine/lysine derivatives, with binary formulations containing the amino acid derivative alone and,DOPE proving superior.

  DOI：

  10.1021/jm010918g

文献信息

• Synthesis of Novel Cationic Lipids:  Effect of Structural Modification on the Efficiency of Gene Transfer
  作者：James A. Heyes、Dan Niculescu-Duvaz、Robert G. Cooper、Caroline J. Springer

  DOI：10.1021/jm010918g

  日期：2002.1.1

  A series of novel cationic lipids was designed and synthesized in an effort to understand the importance of the various structural features with respect to transfection efficiency. Particular attention has been paid to the hydrophobic domain and the cationic headgroup. An efficient method of synthesizing asymmetric diether lipids is described, using alkyl chains ranging from C-12 to C-18 and the unsaturated oleyl group. The ternary formulations including the diether lipid 3beta-[N-(N',N'-dimethylaminoethyl)carbamoyl]cholesterol (DC-Chol) and dioleoyl phosphatidylethanolamine (DOPE) were up to 10-fold more efficacious in in vitro assays than the DC-Chol/DOPE control. The shorter and most asymmetric diether lipids performed the best. The chemical nature and basicity of the headgroups have been varied by the coupling of the four naturally occurring amino acids with cationic side chains-arginine, histidine, lysine, and tryptophan. Transfection efficiency was highest for arginine/lysine derivatives, with binary formulations containing the amino acid derivative alone and,DOPE proving superior.