(3aR,5S,6R,6aR)-6-hydroxy-2,2-dimethyl-N-((S)-pyrrolidin-2-ylmethyl)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxamide | 1599473-99-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5S,6R,6aR)-6-hydroxy-2,2-dimethyl-N-((S)-pyrrolidin-2-ylmethyl)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxamide
• 英文别名: (3aR,5S,6R,6aR)-6-hydroxy-2,2-dimethyl-N-[[(2S)-pyrrolidin-2-yl]methyl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxamide
• CAS: 1599473-99-0
• 化学式: C₁₃H₂₂N₂O₅
• 分子量: 286.328
• InChiKey: MFPZXKQHRJCHGL-OFKSJOQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  89
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S)-benzyl 2-(((3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carboxamido)methyl)pyrrolidine-1-carboxylate 在 氢气 、 钯 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以82%的产率得到(3aR,5S,6R,6aR)-6-hydroxy-2,2-dimethyl-N-((S)-pyrrolidin-2-ylmethyl)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxamide
  参考文献：
  名称：

  Sugar amide-pyrrolidine catalyst for the asymmetric Michael addition of ketones to nitroolefins

  摘要：

  New sugar amide-pyrrolidine derivatives possessing the furano form of the carbohydrate template were designed and developed as efficient and stereoselective organocatalysts for asymmetric Michael additions of ketones to nitroolefins at room temperature. Good yields and high selectivities were achieved with catalyst 2 under solvent-free and additive-free reaction conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.02.003
• 作为试剂：
  描述：

  β-硝基苯乙烯 、 丙酮 在 (3aR,5S,6R,6aR)-6-hydroxy-2,2-dimethyl-N-((S)-pyrrolidin-2-ylmethyl)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxamide 作用下， 反应 56.0h， 以62%的产率得到(R)-5-nitro-4-phenylpentan-2-one
  参考文献：
  名称：

  Sugar amide-pyrrolidine catalyst for the asymmetric Michael addition of ketones to nitroolefins

  摘要：

  New sugar amide-pyrrolidine derivatives possessing the furano form of the carbohydrate template were designed and developed as efficient and stereoselective organocatalysts for asymmetric Michael additions of ketones to nitroolefins at room temperature. Good yields and high selectivities were achieved with catalyst 2 under solvent-free and additive-free reaction conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.02.003

文献信息

• Sugar amide-pyrrolidine catalyst for the asymmetric Michael addition of ketones to nitroolefins
  作者：Togapur Pavan Kumar、Sirinyam Venugopal Balaji

  DOI：10.1016/j.tetasy.2014.02.003

  日期：2014.3

  New sugar amide-pyrrolidine derivatives possessing the furano form of the carbohydrate template were designed and developed as efficient and stereoselective organocatalysts for asymmetric Michael additions of ketones to nitroolefins at room temperature. Good yields and high selectivities were achieved with catalyst 2 under solvent-free and additive-free reaction conditions. (C) 2014 Elsevier Ltd. All rights reserved.