mono-(6-O-phenylacetyl)-β-CD | 1209486-54-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mono-(6-O-phenylacetyl)-β-CD
• CAS: 1209486-54-3
• 化学式: C₅₀H₇₆O₃₆
• 分子量: 1253.13
• InChiKey: SPCOUDSZDQVPPR-CYCIOXFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.44
• 重原子数：
  86.0
• 可旋转键数：
  10.0
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  560.12
• 氢给体数：
  20.0
• 氢受体数：
  36.0

反应信息

• 作为产物：
  描述：

  ethyl phenylacetyl carbonate 、 β-环糊精 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以17%的产率得到mono-(6-O-phenylacetyl)-β-CD
  参考文献：
  名称：

  Synthesis, characterization and potential application of monoacyl-cyclodextrins

  摘要：

  Although the preparation of cyclodextrin (CD) monoesters with a variety of carboxylic acids has been already described in the literature, the direct regioselective CD acylation has proved to be critical often, requiring to be replaced with a more elaborate synthetic process. In this paper we describe the one-step preparation of several monoacylated CDs from acyclic or aromatic carboxylic acid derivatives. The ability of beta-CD to enclose cupric ions in a sandwich-type manner was exploited to lead to high regioselectivity in the acylation of beta-CD with benzoyl chloride, cinnamoyl chloride and phenyl acetyl chloride in water. Long chain aliphatic monoesters of alpha-, beta- and gamma-CD were best reared in DMF. The results of our study showed that solvent and general conditions determined an overwhelming regioselectivity of acylation. H-1, C-13 and 2D NMR experiments could easily discriminate the position of the ester. Monoacylated CDs were evaluated as a carrier of silibinin, the inclusion complexes were prepared and characterized by thermal analysis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.11.009