N-(6-deoxy-β-cyclodextrin-6-yl)-3-(3-methylisoalloxazin-10-yl)propanamide | 1416894-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(6-deoxy-β-cyclodextrin-6-yl)-3-(3-methylisoalloxazin-10-yl)propanamide
• CAS: 1416894-27-3
• 化学式: C₅₆H₈₁N₅O₃₇
• 分子量: 1416.27
• InChiKey: QKNJAYTWPMTFAH-OUDVRRBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -15.11
• 重原子数：
  98.0
• 可旋转键数：
  11.0
• 环数：
  24.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  632.7
• 氢给体数：
  21.0
• 氢受体数：
  41.0

反应信息

• 作为反应物：
  描述：

  N-(6-deoxy-β-cyclodextrin-6-yl)-3-(3-methylisoalloxazin-10-yl)propanamide 、 乙醛 在 高氯酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 21.0h， 生成 N-(6-deoxy-β-cyclodextrin-6-yl)-3-(3-methylisoalloxazin-10-yl)propanamide
  参考文献：
  名称：

  Flavin–cyclodextrin conjugates: effect of the structure on the catalytic activity in enantioselective sulfoxidations

  摘要：

  A series of flavin cyclodextrin conjugates has been prepared and tested in the enantioselective oxidations of prochiral aromatic and aliphatic sulfides with hydrogen peroxide. The newly prepared conjugates contain isoalloxazinium or alloxazinium moieties attached to the primary rim of alpha- and beta-cyclodextrins at the C-6 positions. In addition, flavinium units were attached to the secondary rim of the beta-cyclodextrin macrocycle. The relationship between the structural features and the catalytic performance of the conjugates, including those recently reported by us, was analyzed. The rate and enantioselectivity of the sulfoxidations catalyzed by flavin cyclodextrin conjugates are influenced mainly by the size of the cyclodextrin cavity, the type of flavin unit (alloxazine or isoalloxazine), and by the relative orientation of the flavin and cyclodextrin moieties. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.017
• 作为产物：
  描述：

  3-(3-methylisoalloxazin-10-yl)propionic acid 、 单-6-O-氨基-Β-环糊精 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到N-(6-deoxy-β-cyclodextrin-6-yl)-3-(3-methylisoalloxazin-10-yl)propanamide
  参考文献：
  名称：

  Flavin–cyclodextrin conjugates: effect of the structure on the catalytic activity in enantioselective sulfoxidations

  摘要：

  A series of flavin cyclodextrin conjugates has been prepared and tested in the enantioselective oxidations of prochiral aromatic and aliphatic sulfides with hydrogen peroxide. The newly prepared conjugates contain isoalloxazinium or alloxazinium moieties attached to the primary rim of alpha- and beta-cyclodextrins at the C-6 positions. In addition, flavinium units were attached to the secondary rim of the beta-cyclodextrin macrocycle. The relationship between the structural features and the catalytic performance of the conjugates, including those recently reported by us, was analyzed. The rate and enantioselectivity of the sulfoxidations catalyzed by flavin cyclodextrin conjugates are influenced mainly by the size of the cyclodextrin cavity, the type of flavin unit (alloxazine or isoalloxazine), and by the relative orientation of the flavin and cyclodextrin moieties. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.017