6-O-allylcarbamoyl-β-cyclodextrin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-allylcarbamoyl-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)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-5,15,20,25,30,35-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-10-yl]methyl N-prop-2-enylcarbamate
• 化学式: C₄₆H₇₅NO₃₆
• 分子量: 1218.09
• InChiKey: NFMUMCKFTXKERD-HCHLQLBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -14
• 重原子数：
  83
• 可旋转键数：
  11
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  572
• 氢给体数：
  21
• 氢受体数：
  36

反应信息

• 作为产物：
  描述：

  3-异氰酸丙烯 、 β-环糊精 以 吡啶 为溶剂， 以7%的产率得到6-O-allylcarbamoyl-β-cyclodextrin
  参考文献：
  名称：

  Synthesis and Polymerization of Carbamate-Linked Cyclodextrin Methacrylate Monomers

  摘要：

  A one-step synthesis for cyclodextrin methacrylate monomers was examined starting from alpha-, beta- and gamma-cyclodextrin. The reaction of 2-isocyanatoethyl methacrylate as well as allylisocyanate with the corresponding cyclodextrin gave the monofunctionalized carbamate-linked cyclodextrin methacrylates 2, 6 and 9 and allylcarbamates 11 and 14 in moderate yields. By NMR spectroscopic means, it could be proven that in all cases only the primary 6-hydroxyl groups of the cyclodextrins reacted with the isocyanate group. For the synthesis of a beta-cyclodextrin monoallyl compound, a substitution reaction of purchasable 6-O-monotoluenesulfonyl-beta-cyclodextrin with allylamine gave 6-N-allylamino-6-deoxy-beta-cyclodextrin 18 in high yield. The reaction of 2-isocyanatoethyl methacrylate with alpha-cyclodextrin to the 6-O-carbamoyl-2-methylpropenoylethyl-alpha-cyclodextrin (2) was optimized so that the monomer 2 could be prepared on a larger scale without chromatographic separation. The aqueous radical homopolymerization of 2 with the peroxodisulfate/bisulfite redox initiator gave the water soluble cyclodextrin polymer 19 in good yield. Its molecular weight was determined by gel permeation chromatography to be M-n = 101,800 corresponding to an average degree of polymerization P-n = 90.

  DOI：

  10.1080/07328309808002359

文献信息

• Synthesis and Polymerization of Carbamate-Linked Cyclodextrin Methacrylate Monomers
  作者：Frank Bachmann、Jens Höpken、Rachel Kohli、Dieter Lohmann、Josef Schneider

  DOI：10.1080/07328309808002359

  日期：1998.12

  A one-step synthesis for cyclodextrin methacrylate monomers was examined starting from alpha-, beta- and gamma-cyclodextrin. The reaction of 2-isocyanatoethyl methacrylate as well as allylisocyanate with the corresponding cyclodextrin gave the monofunctionalized carbamate-linked cyclodextrin methacrylates 2, 6 and 9 and allylcarbamates 11 and 14 in moderate yields. By NMR spectroscopic means, it could be proven that in all cases only the primary 6-hydroxyl groups of the cyclodextrins reacted with the isocyanate group. For the synthesis of a beta-cyclodextrin monoallyl compound, a substitution reaction of purchasable 6-O-monotoluenesulfonyl-beta-cyclodextrin with allylamine gave 6-N-allylamino-6-deoxy-beta-cyclodextrin 18 in high yield. The reaction of 2-isocyanatoethyl methacrylate with alpha-cyclodextrin to the 6-O-carbamoyl-2-methylpropenoylethyl-alpha-cyclodextrin (2) was optimized so that the monomer 2 could be prepared on a larger scale without chromatographic separation. The aqueous radical homopolymerization of 2 with the peroxodisulfate/bisulfite redox initiator gave the water soluble cyclodextrin polymer 19 in good yield. Its molecular weight was determined by gel permeation chromatography to be M-n = 101,800 corresponding to an average degree of polymerization P-n = 90.