6-乙酰氨基-β-环糊精 | 131991-70-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-乙酰氨基-β-环糊精
• 英文名称: 6^A-deoxy-6^A-propenamido-β-cyclodextrin
• 英文别名: mono(6-deoxy-6-acrylamido)-β-cyclodextrin；β-cyclodextrin acrylamide；6^A-Acrylamido-6^A-deoxy-β-cyclodextrin；6-Acrylamido-beta-cyclodextrin；N-[[(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)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis(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-5-yl]methyl]prop-2-enamide
• CAS: 131991-70-3
• 化学式: C₄₅H₇₃NO₃₅
• 分子量: 1188.06
• InChiKey: NNRSCYSGPHJCJH-MKWHQSKQSA-N

物化性质

• 熔点：
  236-239 °C (decomp)
• 沸点：
  1585.1±65.0 °C(Predicted)
• 密度：
  1.580±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -14.4
• 重原子数：
  81
• 可旋转键数：
  9
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  563
• 氢给体数：
  21
• 氢受体数：
  35

反应信息

• 作为反应物：
  描述：

  benzohydroximoyl chloride 、 6-乙酰氨基-β-环糊精 在 三乙胺 作用下， 以 水 为溶剂， 反应 15.0h， 以97%的产率得到N-(6^A-deoxy-β-cyclodextrin-6^A-yl)-5-(aminocarbonyl)-3-(phenyl)-4,5-dihydroisoxazole
  参考文献：
  名称：

  β-Cyclodextrin as a Scaffold for Supramolecular Chemistry, To Reverse the Regioselectivity of Nitrile Oxide Cycloadditions

  摘要：

  beta-Cyclodextrin has been used as a molecular scaffold, whereby tethering dipolarophiles to the cyclodextrin and then allowing preassociation of the modified cyclodextrins with aromatic nitrile oxides, as host-guest complexes, controls the relative orientations of the dipoles and the dipolarophiles in their cycloadditions. In this manner it has been possible to reverse the usual regioselectivity of cycloadditions of nitrile oxides, as illustrated by reactions with a terminal alkene, a terminal alkyne, and a 1,2-disubstituted alkene. For example, iii aqueous solution, 4-tert-butylbenzonitrile oxide reacted with 6(A)-deoxy-6(A)-propynamido-beta-cyclodextrin to give the corresponding 4- and 5-substituted isoxazoles, in a 15:1 ratio. With DMF as the solvent, to reduce the extent of host-guest complexation, the product ratio was 1:1.5. The role of complexation in these reactions is also demonstrated by contrasting these results with that of the reaction of the nitrile oxide with methyl propynoate, which afforded only the 5-substituted cycloaddition product. Molecular recognition by the cyclodextrin scaffolds was demonstrated through treatment of 4-tert-butylbenzonitrile oxide with an equimolar mixture of 6(A)-deoxy-6(A)-prapynamido-beta-cyclodextrin and methyl propynoate, in aqueous solution, which gave only the cycloadducts from reaction of the cyclodextrin dipolarophile.

  DOI：

  10.1021/jo9817321
• 作为产物：
  描述：

  单-6-O-氨基-Β-环糊精 、 丙烯酰氯 在 sodium hydroxide 作用下， 以79%的产率得到6-乙酰氨基-β-环糊精
  参考文献：
  名称：

  A cyclodextrin to reverse the regioselectivity of nitrile oxide cycloaddition to a terminal alkene

  摘要：

  在水溶液中，4-叔丁基苯甲腈氧化物与 6 A -丙烯酰胺-6 A -脱氧-β-环糊精进行 1,3- 二极环加成反应，有利于生成 4-取代的异噁唑啉，这与单取代烯反应中通常主要生成 5-取代的调节异构体的情况截然不同。

  DOI：

  10.1039/a703575f

文献信息

• MICROSPHERES CONTAINING THERAPEUTIC AGENTS AND RELATED METHODS OF USE
  申请人：Biosphere Medical, Inc.

  公开号：US20170231915A1

  公开（公告）日：2017-08-17

  Microspheres, compositions including the microspheres, and methods of using the microspheres are disclosed herein. The microspheres can be substantially spherical and can include a copolymer of a monomer (such as an acrylic monomer) and a cyclodextrin or a derivative thereof. The microspheres can also include a therapeutic agent, such as a platinum-based drug.

  本文公开了微球、包括微球的组合物以及使用微球的方法。这些微球可以是基本球形的，可以包括单体的共聚物（如丙烯酸单体）和环糊精或其衍生物。这些微球还可以包括治疗剂，如基于铂的药物。
• [EN] MICROSPHERES CONTAINING THERAPEUTIC AGENTS AND RELATED METHODS OF USE<br/>[FR] MICROSPHÈRES CONTENANT DES AGENTS THÉRAPEUTIQUES ET MÉTHODES D'UTILISATION ASSOCIÉES
  申请人：BIOSPHERE MEDICAL INC

  公开号：WO2019035975A1

  公开（公告）日：2019-02-21

  Microspheres, compositions including the microspheres, and methods of using the microspheres are disclosed herein. The microspheres can be substantially spherical and can include a copolymer of a monomer (such as an acrylic monomer) and a cyclodextrin or a derivative thereof. The microspheres can also include a therapeutic agent, such as a platinum-based drug.

  本文揭示了微球、包括微球的组合物以及使用微球的方法。这些微球可以是基本球形的，并且可以包括单体的共聚物（如丙烯酸单体）和环糊精或其衍生物。微球还可以包括治疗剂，例如基于铂的药物。
• A cyclodextrin to reverse the regioselectivity of nitrile oxide cycloaddition to a terminal alkene
  作者：Adam G. Meyer、Christopher J. Easton、Stephen F. Lincoln、Gregory W. Simpson

  DOI：10.1039/a703575f

  日期：——

  The 1,3-dipolar cycloaddition of 4-tert-butylbenzonitrile oxide with 6 A -acrylamido-6 A -deoxy-β-cyclodextrin in aqueous solution favours formation of the 4-substituted isoxazoline, in contrast to the normal predominance of the 5-substituted regioisomer from reactions of monosubstituted alkenes.

  在水溶液中，4-叔丁基苯甲腈氧化物与 6 A -丙烯酰胺-6 A -脱氧-β-环糊精进行 1,3- 二极环加成反应，有利于生成 4-取代的异噁唑啉，这与单取代烯反应中通常主要生成 5-取代的调节异构体的情况截然不同。
• Macroscopic Observations of Molecular Recognition: Discrimination of the Substituted Position on the Naphthyl Group by Polyacrylamide Gel Modified with β-Cyclodextrin
  作者：Yongtai Zheng、Akihito Hashidzume、Yoshinori Takashima、Hiroyasu Yamaguchi、Akira Harada

  DOI：10.1021/la2034142

  日期：2011.11.15

  Macroscopic molecular recognition observations were realized using polyacrylamide-based gels modified with alpha-cyclodextrin (alpha-CD), beta-cyclodextrin (beta-CD), 1-naphthylmethyl (1Np), and 2-naphthylmethyl (2Np) moieties, which are denoted as alpha CD(x)-gel, beta CD(x)-gel, 1Np(y)-gel, and 2Np(y)-gel, where x and y indicate the mol % of CD and Np moieties, respectively. The alpha CD(5)-gel did not adhere to either the 1Np(5)-gel or 2Np(5)-gel, whereas the beta CD (5)-gel interacted with both to form alternating or checkered assemblies. Although the difference in the association constants of beta-CD for the model polymers was small, the beta CD(x)-gel successfully discriminated between 1Np(y)-gel and 2Np(y)-gel at the appropriate x and y.
• β-Cyclodextrin as a Scaffold for Supramolecular Chemistry, To Reverse the Regioselectivity of Nitrile Oxide Cycloadditions
  作者：Adam G. Meyer、Christopher J. Easton、Stephen F. Lincoln、Gregory W. Simpson

  DOI：10.1021/jo9817321

  日期：1998.11.1

  beta-Cyclodextrin has been used as a molecular scaffold, whereby tethering dipolarophiles to the cyclodextrin and then allowing preassociation of the modified cyclodextrins with aromatic nitrile oxides, as host-guest complexes, controls the relative orientations of the dipoles and the dipolarophiles in their cycloadditions. In this manner it has been possible to reverse the usual regioselectivity of cycloadditions of nitrile oxides, as illustrated by reactions with a terminal alkene, a terminal alkyne, and a 1,2-disubstituted alkene. For example, iii aqueous solution, 4-tert-butylbenzonitrile oxide reacted with 6(A)-deoxy-6(A)-propynamido-beta-cyclodextrin to give the corresponding 4- and 5-substituted isoxazoles, in a 15:1 ratio. With DMF as the solvent, to reduce the extent of host-guest complexation, the product ratio was 1:1.5. The role of complexation in these reactions is also demonstrated by contrasting these results with that of the reaction of the nitrile oxide with methyl propynoate, which afforded only the 5-substituted cycloaddition product. Molecular recognition by the cyclodextrin scaffolds was demonstrated through treatment of 4-tert-butylbenzonitrile oxide with an equimolar mixture of 6(A)-deoxy-6(A)-prapynamido-beta-cyclodextrin and methyl propynoate, in aqueous solution, which gave only the cycloadducts from reaction of the cyclodextrin dipolarophile.