6(I)-[[(2S,4R)-1,2-dibenzyloxycarbonylpyrrolidin-4-yl]4-oxymethyl]-1H-1,2,3-triazol-1-yl-6(I)-deoxy-β-cyclodextrin | 1393739-70-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6(I)-[[(2S,4R)-1,2-dibenzyloxycarbonylpyrrolidin-4-yl]4-oxymethyl]-1H-1,2,3-triazol-1-yl-6(I)-deoxy-β-cyclodextrin
• CAS: 1393739-70-2
• 化学式: C₆₅H₉₂N₄O₃₉
• 分子量: 1553.45
• InChiKey: NZAXHSXMMXRPSA-OKWGJXFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11.89
• 重原子数：
  108.0
• 可旋转键数：
  16.0
• 环数：
  25.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  629.6
• 氢给体数：
  20.0
• 氢受体数：
  42.0

反应信息

• 作为反应物：
  描述：

  6(I)-[[(2S,4R)-1,2-dibenzyloxycarbonylpyrrolidin-4-yl]4-oxymethyl]-1H-1,2,3-triazol-1-yl-6(I)-deoxy-β-cyclodextrin 在 palladium on activated charcoal 、 氢气 作用下， 以 水 为溶剂， 20.0 ℃ 、310.27 kPa 条件下， 反应 48.0h， 以89%的产率得到6(I)-[[(2S,4R)-2-carboxypyrrolidin-4-yl]4-oxymethyl]-1H-1,2,3-triazol-1-yl-6(I)-deoxy-β-cyclodextrin
  参考文献：
  名称：

  Proline–cyclodextrin conjugates: synthesis and evaluation as catalysts for aldol reaction in water

  摘要：

  The synthesis of six conjugates of L-proline and beta-cyclodextrin and their evaluation as catalysts of aldol reaction in water are described. The results indicated that the nature of the linker between proline and beta-cyclodextrin is important for catalytic activity: the one with the most flexible linker gave the best results. Inhibition experiments showed that the cavity of beta-cyclodextrin plays a role in the catalysis. Permethylation of the cyclodextrin hydroxyl groups led to higher conversion rates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.089
• 作为产物：
  描述：

  (2S,4R)-1,2-dibenzyloxycarbonyl-4-(prop-2-yn-1-yloxy)pyrrolidine 、 6A-叠氮基-6A-脱氧-β-环糊精 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以75%的产率得到6(I)-[[(2S,4R)-1,2-dibenzyloxycarbonylpyrrolidin-4-yl]4-oxymethyl]-1H-1,2,3-triazol-1-yl-6(I)-deoxy-β-cyclodextrin
  参考文献：
  名称：

  Proline–cyclodextrin conjugates: synthesis and evaluation as catalysts for aldol reaction in water

  摘要：

  The synthesis of six conjugates of L-proline and beta-cyclodextrin and their evaluation as catalysts of aldol reaction in water are described. The results indicated that the nature of the linker between proline and beta-cyclodextrin is important for catalytic activity: the one with the most flexible linker gave the best results. Inhibition experiments showed that the cavity of beta-cyclodextrin plays a role in the catalysis. Permethylation of the cyclodextrin hydroxyl groups led to higher conversion rates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.089