per-6-[(N,N.N'-trimethyl-2-aminoethyl)amino]-6-deoxy-β-cyclodextrin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: per-6-[(N,N.N'-trimethyl-2-aminoethyl)amino]-6-deoxy-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,46R,47R,48R,49R)-5,10,15,20,25,30,35-heptakis[[2-(dimethylamino)ethyl-methylamino]methyl]-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-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
• 化学式: C₇₇H₁₅₄N₁₄O₂₈
• 分子量: 1724.15
• InChiKey: ATRCGCYHWUQPGS-OJPCCTPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.7
• 重原子数：
  119
• 可旋转键数：
  35
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  458
• 氢给体数：
  14
• 氢受体数：
  42

反应信息

• 作为产物：
  描述：

  七(6-溴-6-脱氧)-beta-环糊精 、 N,N,N'-三甲基乙二胺 反应 12.0h， 生成 per-6-[(N,N.N'-trimethyl-2-aminoethyl)amino]-6-deoxy-β-cyclodextrin
  参考文献：
  名称：

  Synthesis of Monofacially Functionalized Cyclodextrins Bearing Amino Pendent Groups

  摘要：

  Derivatives of the cyclodextrins, alpha CD, beta CD, and gamma CD, in which all primary hydroxyls are substituted by amine pendant groups, may be synthesized efficiently from the per-6-bromo-6-deoxy-CD derivatives by direct reaction with amines. These ACD derivatives, which bear six, seven! or eight amine pendent groups, represent interesting biomimetic receptors and catalysts. The synthetic strategy relies on quantitative transformation and efficient purification as is demonstrated by preparation of 11 homogeneous ACD derivatives. The limitations of the synthesis and potential adaptations are illustrated by the synthesis of several more ACD derivatives to >95% purity. A synthetic route to a CD persubstituted with primary amine functionalities at the primary face, per-6-(aminomethyl)-6-deoxy-CD, yields an alternative reagent to the simple per-6-amino-6-deoxy-CD, which is more suitable for further synthetic transformations. The synthetic strategy is further adapted to preparation of a prototypical (6 + 1)-ACD derivative in which one primary position is substituted with a sulfide group and the remaining six primary face positions are substituted with amine pendent groups.

  DOI：

  10.1021/jo9711549

文献信息

• Synthesis of Monofacially Functionalized Cyclodextrins Bearing Amino Pendent Groups
  作者：Dragos Vizitiu、Caroline S. Walkinshaw、Borio I. Gorin、Gregory R. J. Thatcher

  DOI：10.1021/jo9711549

  日期：1997.12.1

  Derivatives of the cyclodextrins, alpha CD, beta CD, and gamma CD, in which all primary hydroxyls are substituted by amine pendant groups, may be synthesized efficiently from the per-6-bromo-6-deoxy-CD derivatives by direct reaction with amines. These ACD derivatives, which bear six, seven! or eight amine pendent groups, represent interesting biomimetic receptors and catalysts. The synthetic strategy relies on quantitative transformation and efficient purification as is demonstrated by preparation of 11 homogeneous ACD derivatives. The limitations of the synthesis and potential adaptations are illustrated by the synthesis of several more ACD derivatives to >95% purity. A synthetic route to a CD persubstituted with primary amine functionalities at the primary face, per-6-(aminomethyl)-6-deoxy-CD, yields an alternative reagent to the simple per-6-amino-6-deoxy-CD, which is more suitable for further synthetic transformations. The synthetic strategy is further adapted to preparation of a prototypical (6 + 1)-ACD derivative in which one primary position is substituted with a sulfide group and the remaining six primary face positions are substituted with amine pendent groups.