6^A,6^E-Bis(2-naphthylsulfenyl)-γ-cyclodextrin | 140875-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6^A,6^E-Bis(2-naphthylsulfenyl)-γ-cyclodextrin
• CAS: 140875-57-6
• 化学式: C₆₈H₉₂O₃₈S₂
• 分子量: 1581.59
• InChiKey: ZRJVQLZHKSMRND-IQHDQEFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.5
• 重原子数：
  108.0
• 可旋转键数：
  12.0
• 环数：
  34.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  592.74
• 氢给体数：
  22.0
• 氢受体数：
  40.0

反应信息

• 作为产物：
  描述：

  sodium 2-naphthalenethiolate 、 6^A,6^E-Bis(2-naphthylsulfonyl)-γ-cyclodextrin 以 二甲基亚砜 为溶剂， 反应 5.0h， 以23%的产率得到6^A,6^E-Bis(2-naphthylsulfenyl)-γ-cyclodextrin
  参考文献：
  名称：

  Host-guest sensors of 6A,6B-, 6A,6C-, 6A,6D-, and 6A,6E-bis(2-naphthylsulfenyl)-.gamma.-cyclodextrins for detecting organic compounds by fluorescence enhancements

  摘要：

  Gamma-cyclodextrin derivatives 1-4 which have two naphthyl moleties at AB, AC, AD, and AE glucose residues, respectively, have been prepared as a series of sensors for detecting organic compounds. They exhibit almost pure monomer fluorescence whose intensity is enhanced upon addition of guest species. The value Im/Im-degrees, where Im and Im-degrees are fluorescence intensities in the presence and absence of a guest, was used as a sensitivity parameter. The data for twelve organic compounds were collected. Four steroidal compounds such as cholic acid (5), deoxycholic acid (6), chenodeoxycholic acid (7), and ursodeoxycholic acid (8) were detected by 1, 2, and 3 with the order of the sensitivity 5 < 6 < 7 < 8 while they were detected by 4 with the order 8 < 5 < 7 < 6. Three alcohols such as l-borneol (9), cyclohexanol (10), and cyclododecanol (12) were detected by 1-4 with the order of the sensitivity 10 < 9 < 12. 1-Adamantanecarboxylic acid (11) exhibits sensitivities comparable to those of bicyclic compound 9. Nerol (13), geraniol (14), d-menthol (15), and l-menthol (16) were detected with much smaller sensitivities than 9, and geometrical and chiral discrimination for them was not appreciable. Binding constants of 1-4 for 5, 9, 11, and 12 were obtained. Among four hosts, 2 gave the largest binding constant for each of the guests. The binding constants of 2 for the guests are in the order 9 < 11 < 5 < 12 and roughly parallel with the sensitivity parameters.

  DOI：

  10.1021/ac00034a014