4-N-[4-[[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-1-hydroxyethylidene]amino]-2,5-didodecoxyphenyl]-1-N-[4-[[[4-[N-[4-[[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-1-hydroxyethylidene]amino]-2,5-didodecoxyphenyl]-C-hydroxycarbonimidoyl]-2,5-didodecoxyphenyl]-hydroxymethylidene]amino]-2,5-didodecoxyphenyl]-2,5-didodecoxybenzene-1,4-dicarboximidic acid | 1263320-98-4

• 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: 4-N-[4-[[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-1-hydroxyethylidene]amino]-2,5-didodecoxyphenyl]-1-N-[4-[[[4-[N-[4-[[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-1-hydroxyethylidene]amino]-2,5-didodecoxyphenyl]-C-hydroxycarbonimidoyl]-2,5-didodecoxyphenyl]-hydroxymethylidene]amino]-2,5-didodecoxyphenyl]-2,5-didodecoxybenzene-1,4-dicarboximidic acid
• CAS: 1263320-98-4
• 化学式: C₂₁₂H₃₆₀N₆O₁₈
• 分子量: 3281.22
• InChiKey: HLKIOUGVYHPTJU-FFIADYFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  80.1
• 重原子数：
  236
• 可旋转键数：
  146
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  306
• 氢给体数：
  6
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  N-(4-amino-2,5-bis(dodecyloxy)phenyl)-2-(((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)acetamide 、 4,4'-(((2,5-bis(dodecyloxy)-1,4-phenylene)bis(azanediyl))bis(carbonyl))bis(2,5-bis(dodecyloxy)benzoic acid) 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 氯仿 为溶剂， 以45%的产率得到4-N-[4-[[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-1-hydroxyethylidene]amino]-2,5-didodecoxyphenyl]-1-N-[4-[[[4-[N-[4-[[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-1-hydroxyethylidene]amino]-2,5-didodecoxyphenyl]-C-hydroxycarbonimidoyl]-2,5-didodecoxyphenyl]-hydroxymethylidene]amino]-2,5-didodecoxyphenyl]-2,5-didodecoxybenzene-1,4-dicarboximidic acid
  参考文献：
  名称：

  Hydrogen bonded arylamide-linked cholesteryl dimesogenic liquid crystals: a study of the length and side chain effects

  摘要：

  Dimesogenic compounds 1a-c, 2a-i, and 3, that are composed of a hydrogen bonding-induced straight arylamide spacer and two appended cholesterol groups, have been designed and synthesized. The backbones of the rigid spacers of 1a-c, 2a-i, and 3 contain one, three, and five benzene units, which bear two, six, and ten alkoxyl (methoxyl, n-octoxyl, or n-dodecoxyl) groups, respectively. The thermal and optical properties of the compounds are investigated by using the differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and powder X-ray diffraction (PXRD) analysis. It is revealed that la c exhibit one or two liquid crystalline (LC) phases, 2a-i exhibit no, one or two LC phases, while 3 exhibits one LC phase in a wide temperature range. Generally, the more and longer alkoxyl chains facilitate the formation of the LC phases at low temperature. Notably, compound 2g, which bears two methoxyl and four dodecoxyl groups, displays a blue-red color change during both the heating and cooling cycle. The result illustrates that dimesogens with large rigid spacers can exhibit different LC phases when long aliphatic chains are appended to balance the strong stacking of the rigid backbones. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.046