β-cyclodextrin 6-O-monobenzoate | 144363-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-cyclodextrin 6-O-monobenzoate
• 英文别名: mono-6-O-benzoyl-β-cyclodextrin；β-cyclodextrin 6-O-benzoate；6-O-benzoyl-β-cyclodextrin；mono-(6-O-benzoyl)-β-CD
• CAS: 144363-18-8
• 化学式: C₄₉H₇₄O₃₆
• 分子量: 1239.1
• InChiKey: GAOLIIVLYNULNX-DBKPRUCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.37
• 重原子数：
  85.0
• 可旋转键数：
  9.0
• 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：

  苯甲酸 、 β-环糊精 在 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 以81%的产率得到β-cyclodextrin 6-O-monobenzoate
  参考文献：
  名称：

  Direct esterification of the hydroxyl groups of β-cyclodextrin with some aromatic monocarboxylic acids

  摘要：

  A possibility of the direct monoesterification of beta-cyclodextrin with benzoic, p-aminobenzoic, 2-(4-isobutylphenyl)propionic, nicotinic, and isonicotinic acids was shown. Regioselectivity of substitution on the primary hydroxyl groups was confirmed by the means of H-1 and C-13 NMR spectroscopy.

  DOI：

  10.1134/s107036321511016x

文献信息

• Synthesis, characterization and potential application of monoacyl-cyclodextrins
  作者：Katia Martina、Devendra Sharad Puntambekar、Alessandro Barge、Marina Gallarate、Daniela Chirio、Giancarlo Cravotto

  DOI：10.1016/j.carres.2009.11.009

  日期：2010.1

  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.
• Tong, Lin-Hui; Hou, Zhi-Jie; Inoue, Yoshihisa, Journal of the Chemical Society. Perkin transactions II, 1992, # 8, p. 1253 - 1257
  作者：Tong, Lin-Hui、Hou, Zhi-Jie、Inoue, Yoshihisa、Tai, Akira

  DOI：——

  日期：——