4′-((5-cholesteryloxy-5-oxopentyl)oxy)biphenyl-4-yl 4-(octyloxy)benzoate | 1616352-77-2

• 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′-((5-cholesteryloxy-5-oxopentyl)oxy)biphenyl-4-yl 4-(octyloxy)benzoate
• 英文别名: [4-[4-[5-[[(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]-5-oxopentoxy]phenyl]phenyl] 4-octoxybenzoate
• CAS: 1616352-77-2
• 化学式: C₅₉H₈₂O₆
• 分子量: 887.296
• InChiKey: GZOWSWWAJDPIGY-KWDDHKSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.9
• 重原子数：
  65
• 可旋转键数：
  25
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  cholest-5-en-3-β-yl 5-bromopentanoate 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 4′-((5-cholesteryloxy-5-oxopentyl)oxy)biphenyl-4-yl 4-(octyloxy)benzoate
  参考文献：
  名称：

  Synthesis and characterization of novel chiral dimers exhibiting highly frustrated liquid crystal phases

  摘要：

  Two novel series of optically active dimers comprising cholesterol and biphenyl-4-yl 4-(n-alkoxy)benzoate cores interlinked though either an odd-parity/even-parity spacer have been prepared and characterized. They stabilize an extremely complex, frustrated liquid crystalline state viz., the twist grain boundary (TGB) phase with chiral smectic C structure, denoted as TGBC* phase, over a wide (50-110 degrees C) temperature range. Notably, the dimers with an odd-parity spacer show an additional frustrated liquid crystal phase namely, the blue phase (BP). The presence of such frustrated phases suggests that the synthesized dimers are characterized by high enantiomeric excess and strong molecular chirality. Thus, 12 new optically active, nonsymmetric dimers reported herein constitute new examples of rarely found strongly chiral, optically pure dimers showing frustrated liquid crystal phase over an adequately wide thermal range. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.05.072