mono-2-O-ethyl-β-cyclodextrin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mono-2-O-ethyl-β-cyclodextrin
• 英文别名: (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46S,47R,48R,49R)-47-ethoxy-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,48,49-tridecol
• 化学式: C₄₄H₇₄O₃₅
• 分子量: 1163.05
• InChiKey: FVRFOYJRVRJJJG-LRCRDJQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -14.1
• 重原子数：
  79
• 可旋转键数：
  9
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  543
• 氢给体数：
  20
• 氢受体数：
  35

反应信息

• 作为产物：
  描述：

  硫酸二乙酯 、 β-环糊精 在 sodium hydroxide 作用下， 反应 20.0h， 以580 mg的产率得到mono-2-O-ethyl-β-cyclodextrin
  参考文献：
  名称：

  Regioselectivity of alkylation of cyclomaltoheptaose (β-cyclodextrin) and synthesis of its mono-2-O-methyl, -ethyl, -allyl, and -propyl derivatives

  摘要：

  Mono-2-O-methyl-, -2-O-ethyl-, and -2-O-allyl-cyclomaltoheptaose were prepared by alkylations of cyclomaltoheptaose in dilute aqueous alkali, and mono-2-O-propylcyclomaltoheptaose was obtained by hydrogenation of the allyl derivative. Ah the 2-O-alkyl derivatives were less soluble in water than was cyclomaltoheptaose. All formed inclusion complexes with toluene in aqueous solution, but only the methyl ether was less soluble in the water-toluene system than in water. The solubilities of the other ethers in water were enhanced by the addition of toluene. Partial methylation of cyclomaltoheptaose with C-13-enriched dimethyl sulfate in dilute aqueous alkali yielded mixtures of products. The substitution patterns were analyzed by GLC-MS of the alditol acetates, prepared by hydrolysis, reduction, and acetylation, and by C-13 NMR after complete permethylation with nonenriched reagent. The results showed that methylation at O-2 is a predominant but not an exclusive reaction; as expected, the regioselectivity decreases with increasing degree of methylation.

  DOI：

  10.1016/0008-6215(94)00251-a