mono-3-O-(p-methylbenzoyl)-β-CD | 1179857-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mono-3-O-(p-methylbenzoyl)-β-CD
• 英文别名: mono-3-(p-methylbenzoyl)-β-CD；mono-3-O-(p-methylbenzoyl)-β-cyclodextrin；mono-2-O-(p-methylbenzoyl)-β-CD；[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26R,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,41,42,43,44,45,46,47,48,49-tridecahydroxy-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]nonatetracontan-40-yl] 4-methylbenzoate
• CAS: 1179857-38-5
• 化学式: C₅₀H₇₆O₃₆
• 分子量: 1253.13
• InChiKey: LARIEDUULFTHQB-SESUZMAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -12.4
• 重原子数：
  86
• 可旋转键数：
  10
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  560
• 氢给体数：
  20
• 氢受体数：
  36

反应信息

• 作为反应物：
  描述：

  mono-3-O-(p-methylbenzoyl)-β-CD 生成 对甲基苯甲酸 、 β-环糊精
  参考文献：
  名称：

  Direct Regioselective Esterification atO-2 of β-Cyclodextrin and Hydrolysis by Neighboring-group Participation

  摘要：

  使用N,N'-碳酰亚胺和碳酸盐缓冲液在1,4-二氧六环中开发了一种直接选择性酯化β-环糊精的简单高效策略，该策略不需要大量极性有机溶剂（如DMF）、有毒溶剂（如CH₃CN）或易燃碱（如NaH）。此外，观察到它们通过邻基参与的水解作用。单-2-对甲苯磺酰基-β-环糊精易于环氧化，而单-2-(对甲苯甲酰)-β-环糊精易于异构化。它们具有不同的水解机制。

  DOI：

  10.1155/2012/398683
• 作为产物：
  描述：

  mono-2-O-(p-methylbenzoyl)-β-CD 以 甲醇 、 水 为溶剂， 反应 1.0h， 以0.87 g的产率得到mono-3-O-(p-methylbenzoyl)-β-CD
  参考文献：
  名称：

  β-环糊精在仲羟基面上的直接芳基化：通过C 2-O-芳酰基到C 3-O-芳酰基迁移的方便的依赖于平衡的单-3-芳酰基-β-环糊精制备方法

  摘要：

  摘要提出了一种在碳酸盐缓冲溶液中使用N-苯并咪唑对β-环糊精进行直接区域选择性苯甲酰化制备单-3- O-苯甲酰基-β-环糊精的简便方法。该过程涉及平衡依赖性的C2 - O-芳酰基向C3- O-芳酰基的迁移，以提高产率。 图形概要

  DOI：

  10.1007/s00706-012-0749-x

文献信息

• Direct regioselective benzoylation of a single C-2 hydroxyl group of β-cyclodextrin and its hydrolysis via benzoyl group migration
  作者：Zhi-zhong Wang、Meng-ying Liu、Run-hua Lu、Xue-yan Fu、Gui-dong Dai

  DOI：10.1007/s00706-011-0566-7

  日期：2011.12

  benzoylation of a single C-2 hydroxyl group of β-cyclodextrin was developed by using a combination of N,N′-carbonyldiimidazole and carbonate buffer in 1,4-dioxane, which does not require highly reactive reagents such as acyl chloride, or toxic solvents such as acetonitrile. Moreover, hydrolysis of the product was determined to occur via benzoyl group migration. Graphical abstract

  摘要结合N，N'-羰基二咪唑和碳酸盐缓冲液在1,4-二恶烷中的组合，开发了一种简单有效的直接对β-环糊精的单C-2羟基进行区域选择性苯甲酰基化的方法。反应性试剂（如酰氯）或有毒溶剂（如乙腈）。此外，确定产物的水解是通过苯甲酰基迁移发生的。 图形概要
• Direct Regioselective Esterification at<i>O</i>-2 of β-Cyclodextrin and Hydrolysis by Neighboring-group Participation
  作者：Zhi-Zhong Wang、Xuan-Ping Ma、Xiao-Gang Wei

  DOI：10.1155/2012/398683

  日期：——

  A simple and efficient strategy for direct regioselective esterification atO-2 of β-cyclodextrin was developed by using the combination of N,N'-carbonyldiimidazole and carbonate buffer in 1,4-dioxane, which does not require large amounts of polar organic solvents such as DMF, toxic solvents such as CH₃CN, or flammable bases such as NaH. Moreover, their hydrolyses by neighboring-group participation were observed. Mono-2-tosyl-β-cyclodextrin was liable to epoxidation, while mono-2-(p-methylbenzoyl)-β-cyclodextrin liable to isomerization. They had different mechanisms of hydrolysis.

  使用N,N'-碳酰亚胺和碳酸盐缓冲液在1,4-二氧六环中开发了一种直接选择性酯化β-环糊精的简单高效策略，该策略不需要大量极性有机溶剂（如DMF）、有毒溶剂（如CH₃CN）或易燃碱（如NaH）。此外，观察到它们通过邻基参与的水解作用。单-2-对甲苯磺酰基-β-环糊精易于环氧化，而单-2-(对甲苯甲酰)-β-环糊精易于异构化。它们具有不同的水解机制。
• Direct aroylation of β-cyclodextrin on the secondary hydroxyl face: a convenient equilibrium-dependent preparation of mono-3-aroyl-β-cyclodextrin via C2-O-aroyl to C3-O-aroyl group migration
  作者：Zhi-zhong Wang、Qing Huang、Shi-jie Wei、Lei Sun、Jing Chen

  DOI：10.1007/s00706-012-0749-x

  日期：2012.12

  AbstractA new and convenient method is presented for the preparation of mono-3-O-benzoyl-β-cyclodextrin by direct regioselective benzoylation of β-cyclodextrin using N-benzoylimidazole in carbonate buffer solution. This process involved equilibrium-dependent C2-O-aroyl to C3-O-aroyl group migration to improve the yield. Graphical abstract

  摘要提出了一种在碳酸盐缓冲溶液中使用N-苯并咪唑对β-环糊精进行直接区域选择性苯甲酰化制备单-3- O-苯甲酰基-β-环糊精的简便方法。该过程涉及平衡依赖性的C2 - O-芳酰基向C3- O-芳酰基的迁移，以提高产率。 图形概要