mono(2^A-O-(α-(4-toluonitrile)))heptakis(6-O-tert-butyldimethylsilyl)-β-cyclodextrin | 171614-13-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mono(2^A-O-(α-(4-toluonitrile)))heptakis(6-O-tert-butyldimethylsilyl)-β-cyclodextrin
• 英文别名: mono(2^A-O-[α-(4-toluonitrile)])heptakis(6-O-tert-butyldimethylsilyl)-β-cyclodextrin
• CAS: 171614-13-4
• 化学式: C₉₂H₁₇₃NO₃₅Si₇
• 分子量: 2049.97
• InChiKey: LSLWYWRVDHSIIT-ZKBKXVKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.07
• 重原子数：
  135.0
• 可旋转键数：
  24.0
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  489.84
• 氢给体数：
  13.0
• 氢受体数：
  36.0

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 mono(2^A-O-(α-(4-toluonitrile)))heptakis(6-O-tert-butyldimethylsilyl)-β-cyclodextrin 在 barium dihydroxide 、 barium(II) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以85%的产率得到mono(2^A-O-(α-(4-toluonitrile)))hexakis(2^B,2^C,2^D,2^E,2^F,2^G-O-methyl)heptakis(6-O-tert-butyldimethylsilyl)-β-cyclodextrin
  参考文献：
  名称：

  Selective Functionalization and Flexible Coupling of Cyclodextrins at the Secondary Hydroxyl Face

  摘要：

  Methods are described for the chemo- and regioselective monofunctionalization of the secondary hydroxyl face of cyclodextrins. Monofunctionalization takes place either by nucleophilic epoxide opening of mono(2(A),3(A)-anhydro)heptakis(6-O-tert-butyldimethylsilyl)-(2(A)S)-beta-cylodextrin by ethylenediamine, lithium azide, or ammonia or by direct monoalkylation of one of the C(2)-hydroxyl groups of heptakis(6-O-tert-butyldimethylsilyl)cyclodextrins with primary alkyl bromides, with cyano-, ethynyl-, or ester-containing functional groups. The latter route enables the synthesis of mono(2(A)-O-(alpha-(4-(aminomethyl)tolyl))hexakis(2(B),2(C),2(D),2(E),2(F),2(G),-O-methyl)heptakis(6-O-tert-butyldimethylsilyl)-beta-cyclodextrin and its 2-aminomethyl isomer. These are lipophilic precursors for cyclodextrin derivatives having one reactive functional group and an enlarged molecular cavity formed by partial methylation of the secondary hydroxyl face. The direct monoalkylation route of the secondary face leaves the structure of the cavity intact, while this is distorted in the route using nucleophilic epoxide opening. Two amino-functionalized cyclodextrins were used for coupling reactions with a monofunctionalized calix[4]arene. In this way water-soluble cyclodextrin derivatives could be obtained of which the secondary faces were flexibly capped with a calix[4]arene moiety.

  DOI：

  10.1021/jo00125a045
• 作为产物：
  描述：

  七-6-(二甲基-叔-丁基甲硅烷基)-β-环糊精 、 对氰基溴化苄 生成 mono(2^A-O-(α-(4-toluonitrile)))heptakis(6-O-tert-butyldimethylsilyl)-β-cyclodextrin
  参考文献：
  名称：

  Novel water-soluble cyclodextrin–calix[4]arene host molecules with strongly enhanced binding properties

  摘要：

  beta-Cyclodextrins appended with a calix[4]arene moiety at the secondary face are very efficient host molecules for the fluorescent dyes 1-anilino-8-naphthalenesulfonate and 2-p-toluidino-6-naphthalenesulfonate with unprecedented high complexation constants.

  DOI：

  10.1039/c39950001151