methyl (4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-bis[[2-(benzimidazol-1-yl)acetyl]oxy]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate | 923014-04-4

• 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: methyl (4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-bis[[2-(benzimidazol-1-yl)acetyl]oxy]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 923014-04-4
• 化学式: C₄₃H₅₄N₄O₆
• 分子量: 722.925
• InChiKey: AMYNAJMYQZIKML-OSDSCPMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  53
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-bis[[2-(benzimidazol-1-yl)acetyl]oxy]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate 、 1,8-双(溴甲基)萘 以 乙腈 为溶剂， 反应 23.0h， 以73%的产率得到
  参考文献：
  名称：

  Design of steroid-based imidazolium receptors for fluoride ion recognition

  摘要：

  New deoxycholic acid-based cyclic receptors bearing imidazolium and benzimidazolium moieties bridged with o-xylelene and 1,8-dimethylenenaphthalene groups have been synthesized. Anion binding studies using H-1 NMR revealed that receptors having naphthalenic group as spacer exhibit very high selectivity for fluoride ion over other anions while receptors with o-xylelene group show a preference for the chloride ion. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.065
• 作为产物：
  描述：

  methyl 3,7,12-trideoxy-3α,12α-bis(2-bromoacetyloxy)cholate 、 苯并咪唑 以 四氢呋喃 为溶剂， 反应 8.0h， 以75%的产率得到methyl (4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-bis[[2-(benzimidazol-1-yl)acetyl]oxy]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
  参考文献：
  名称：

  Anion recognition by bisimidazolium and bisbenzimidazolium cholapods

  摘要：

  Bile acid-based acyclic receptors bearing two imidazole and benzimidazole moieties have been synthesized. Anion binding studies using H-1 NMR revealed that imidazolium receptor exhibits high selectivity for chloride ion while benzimidazolium receptor showed selectivity for Y-shaped acetate ion through hydrogen bond interactions involving imidazolium C-2 and acetyl methylene hydrogens. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.10.037

文献信息

• Bile Acid-Based Cyclic Bisbenzimidazolium Receptors for Anion Recognition:  Highly Improved Receptors for Fluoride and Chloride Ions
  作者：Vijay K. Khatri、Mamta Chahar、K. Pavani、Pramod S. Pandey

  DOI：10.1021/jo701341r

  日期：2007.12.1

  The anion binding properties of bile acid-based cyclic bisbenzimidazolium receptors 6-8 bridged with in-xylene, p-xylene, and 2,6-dimethylpyridine have been studied. Receptors 6 and 7 exhibit much higher binding affinity for fluoride and chloride ions, respectively, as compared to the imidazolium receptors 1 and 2. Receptor 8, however, shows high selectivity but very low binding affinity for anions due to the presence of pyridyl nitrogen. The single-crystal X-ray structure of imidazolium receptor 10-(Br)(2) containing pyridyl spacer reveals the binding pattern.
• Design of steroid-based imidazolium receptors for fluoride ion recognition
  作者：Mamta Chahar、Pramod S. Pandey

  DOI：10.1016/j.tet.2008.04.065

  日期：2008.6

  New deoxycholic acid-based cyclic receptors bearing imidazolium and benzimidazolium moieties bridged with o-xylelene and 1,8-dimethylenenaphthalene groups have been synthesized. Anion binding studies using H-1 NMR revealed that receptors having naphthalenic group as spacer exhibit very high selectivity for fluoride ion over other anions while receptors with o-xylelene group show a preference for the chloride ion. (c) 2008 Elsevier Ltd. All rights reserved.
• Anion recognition by bisimidazolium and bisbenzimidazolium cholapods
  作者：Mamta Chahar、Shailesh Upreti、Pramod S. Pandey

  DOI：10.1016/j.tet.2006.10.037

  日期：2007.1

  Bile acid-based acyclic receptors bearing two imidazole and benzimidazole moieties have been synthesized. Anion binding studies using H-1 NMR revealed that imidazolium receptor exhibits high selectivity for chloride ion while benzimidazolium receptor showed selectivity for Y-shaped acetate ion through hydrogen bond interactions involving imidazolium C-2 and acetyl methylene hydrogens. (c) 2006 Published by Elsevier Ltd.