3,3'-((3-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)propyl)azanediyl)dipropanenitrile | 1170726-27-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3,3'-((3-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)propyl)azanediyl)dipropanenitrile
• CAS: 1170726-27-8
• 化学式: C₃₆H₅₉N₃O
• 分子量: 549.884
• InChiKey: PUZWPHWPYFUXGV-ZDEQVQIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.93
• 重原子数：
  40.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  60.05
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 3,3'-((3-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)propyl)azanediyl)dipropanenitrile 在 sodium tetrahydroborate 、 nickel (II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以68%的产率得到di-tert-butyl (((3-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)propyl)azanediyl)bis(propane-3,1-diyl))dicarbamate
  参考文献：
  名称：

  Synthesis of novel cholesterol-based cationic lipids for gene delivery

  摘要：

  The new cholesterol-based cationic lipids B, C, and D with an ether linked spacer were synthesized by using aminopropyl chain extension with acrylonitrile. The cholesterol-based cationic lipid A with carbamoyl linkage were also synthesized in order to compare the difference in transfection efficiency of the two linkage types. To this end, GFP expression of these cationic lipids was confirmed respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.036
• 作为产物：
  描述：

  3-[(3beta)-胆甾-5-烯-3-基氧基]-1-丙胺 、 丙烯腈 以 甲醇 为溶剂， 以42%的产率得到3-((3-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)propyl)amino)propanenitrile
  参考文献：
  名称：

  Synthesis of novel cholesterol-based cationic lipids for gene delivery

  摘要：

  The new cholesterol-based cationic lipids B, C, and D with an ether linked spacer were synthesized by using aminopropyl chain extension with acrylonitrile. The cholesterol-based cationic lipid A with carbamoyl linkage were also synthesized in order to compare the difference in transfection efficiency of the two linkage types. To this end, GFP expression of these cationic lipids was confirmed respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.036