6-O-(p-(Allyloxy)phenyl)heptakis(2,3-di-O-methyl)-β-cyclodextrin | 150885-12-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(p-(Allyloxy)phenyl)heptakis(2,3-di-O-methyl)-β-cyclodextrin
• 英文别名: 6-O-[p-(Allyloxy)phenyl]heptakis(2,3-di-O-methyl)-β-cyclodextrin
• CAS: 150885-12-4
• 化学式: C₆₅H₁₀₆O₃₆
• 分子量: 1463.54
• InChiKey: BPLMMAWKWSUGCL-IORFNPNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.42
• 重原子数：
  101.0
• 可旋转键数：
  26.0
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  398.28
• 氢给体数：
  6.0
• 氢受体数：
  36.0

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 6-O-(p-(Allyloxy)phenyl)heptakis(2,3-di-O-methyl)-β-cyclodextrin 在 吡啶 作用下， 以74%的产率得到6^A-O-(p-(Allyloxy)phenyl)heptakis(2,3-di-O-methyl)-6^B,6^C,6^D,6^E,6^F,6^G-hexa-O-(methanosulfonyl)-β-cyclodextrin
  参考文献：
  名称：

  New permethyl-substituted .beta.-cyclodextrin polysiloxanes for use as chiral stationary phases in open tubular column chromatography

  摘要：

  Heptakis(2,3-di-O-methyl)-6-O-tosyl-beta-cyclodextrin (2) was prepared from heptakis(2,3-di-O-methyl)-beta-cyclodextrin (1) in a 31 % yield. The tosyl group of 2 was substituted by p-(allyloxy)phenyl in a yield of 74 % to produce 6-O-(p-(allyloxy)phenyl)heptakis(2,3-di-O-methyl)-beta-cyclodextrin (3). This material was derivatized at the other 6-positions to produce persubstituted 6A-O-(p-(allyloxy)phenyl)-beta-cyclodextrins 4, 5, and 8. Permethylated 6-O-tosyl-beta-cyclodextrin 9, which was used for the preparation of 10-12, was obtained from 2 almost quantitatively. 6-O-(tert-Butyldimethylsilyl)-(heptakis(2,3-di-O-methyl)-beta-cyclodextrin (13) was also obtained from 1 in a 33% yield. Permethylated 6A-deoxy-6A-methylene-beta-cyclodextrin (17) was prepared from 13 by a 4-step process. Seven new permethyl-substituted beta-cyclodextrins bound to polymethylsiloxane were prepared by a hydrosilylation reaction of the permethyl-substituted monoalkenyl-beta-cyclodextrins with polyhydromethylsiloxane. The polymeric phases provide excellent enantiomeric separation of a variety of chiral solutes in open tubular column supercritical fluid chromatography (SFC) and gas chromatography (GC).

  DOI：

  10.1021/jo00070a019
• 作为产物：
  描述：

  4-丙烯氧基苯酚 、 heptakis(2,3-di-O-methyl)-6I-O-p-tolylsulfonyl-cyclomaltoheptaose 在 sodium hydride 作用下， 以74%的产率得到6-O-(p-(Allyloxy)phenyl)heptakis(2,3-di-O-methyl)-β-cyclodextrin
  参考文献：
  名称：

  New permethyl-substituted .beta.-cyclodextrin polysiloxanes for use as chiral stationary phases in open tubular column chromatography

  摘要：

  Heptakis(2,3-di-O-methyl)-6-O-tosyl-beta-cyclodextrin (2) was prepared from heptakis(2,3-di-O-methyl)-beta-cyclodextrin (1) in a 31 % yield. The tosyl group of 2 was substituted by p-(allyloxy)phenyl in a yield of 74 % to produce 6-O-(p-(allyloxy)phenyl)heptakis(2,3-di-O-methyl)-beta-cyclodextrin (3). This material was derivatized at the other 6-positions to produce persubstituted 6A-O-(p-(allyloxy)phenyl)-beta-cyclodextrins 4, 5, and 8. Permethylated 6-O-tosyl-beta-cyclodextrin 9, which was used for the preparation of 10-12, was obtained from 2 almost quantitatively. 6-O-(tert-Butyldimethylsilyl)-(heptakis(2,3-di-O-methyl)-beta-cyclodextrin (13) was also obtained from 1 in a 33% yield. Permethylated 6A-deoxy-6A-methylene-beta-cyclodextrin (17) was prepared from 13 by a 4-step process. Seven new permethyl-substituted beta-cyclodextrins bound to polymethylsiloxane were prepared by a hydrosilylation reaction of the permethyl-substituted monoalkenyl-beta-cyclodextrins with polyhydromethylsiloxane. The polymeric phases provide excellent enantiomeric separation of a variety of chiral solutes in open tubular column supercritical fluid chromatography (SFC) and gas chromatography (GC).

  DOI：

  10.1021/jo00070a019