Imidazole-1-carboxylic acid (S)-4-methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexyl ester | 286949-85-7

• 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: Imidazole-1-carboxylic acid (S)-4-methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexyl ester
• CAS: 286949-85-7
• 化学式: C₃₂H₄₆N₂O₂
• 分子量: 490.729
• InChiKey: IAWMXZALKZQKST-VBVDVLQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.53
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  三(2-氨基乙基)胺 、 Imidazole-1-carboxylic acid (S)-4-methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexyl ester 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 [(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexyl] N-[2-[bis(2-aminoethyl)amino]ethyl]carbamate
  参考文献：
  名称：

  Synthesis and evaluation of vitamin D-based cationic lipids for gene delivery in vitro

  摘要：

  A new panel of steroidal cationic lipids has been synthesized for gene delivery. Using commercially available vitamin D-2 (calciferol) or vitamin D-3 (cholecalciferol) as hydrophobic motifs and a variety of cationic head groups as binding sites for negatively charged phosphate groups in DNA, we demonstrated that the transfection activity of the synthetic vitamin D-based cationic lipids 1d, 2d formulated with dioleoylphosphatidylethanolamine (DOPE) as a co-lipid is comparable to that of 3-(-[N-N',N'-dimethylaminoethane)carbamoyl]cholesterol (DC-Chol). These synthetic lipids are effective in transfecting a variety of cell lines. These results suggest that vitamin D-based cationic lipids are useful transfection reagents for in vitro gene transfer studies. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(00)00127-x
• 作为产物：
  描述：

  维生素D2 、 N,N'-羰基二咪唑 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到Imidazole-1-carboxylic acid (S)-4-methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexyl ester
  参考文献：
  名称：

  Synthesis and evaluation of vitamin D-based cationic lipids for gene delivery in vitro

  摘要：

  A new panel of steroidal cationic lipids has been synthesized for gene delivery. Using commercially available vitamin D-2 (calciferol) or vitamin D-3 (cholecalciferol) as hydrophobic motifs and a variety of cationic head groups as binding sites for negatively charged phosphate groups in DNA, we demonstrated that the transfection activity of the synthetic vitamin D-based cationic lipids 1d, 2d formulated with dioleoylphosphatidylethanolamine (DOPE) as a co-lipid is comparable to that of 3-(-[N-N',N'-dimethylaminoethane)carbamoyl]cholesterol (DC-Chol). These synthetic lipids are effective in transfecting a variety of cell lines. These results suggest that vitamin D-based cationic lipids are useful transfection reagents for in vitro gene transfer studies. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(00)00127-x