N-benzyl-N-((3aR,6aR)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)hydroxylamine | 1161850-37-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-N-((3aR,6aR)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)hydroxylamine
• CAS: 1161850-37-8
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: JNORYJPKGBCVEN-ZNRZSNADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  51.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-((3aR,6aR)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)hydroxylamine 、 马来酸二甲酯 反应 12.0h， 以71%的产率得到dimethyl (3S,4R,5S)-2-benzyl-3-[(4'S,5'R)-5'-(hydroxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4,5-isoxazolidinedicarboxylate
  参考文献：
  名称：

  N-Glycosylhydroxylamines as Masked Polyhydroxylated Chiral Nitrones in Cycloaddition Reactions: An Access to Pyrrolizidines

  摘要：

  N-glycosylhydroxylamines undergo 1,3-dipolar cycloadditions via their tautomeric open chain nitrones. Cycloadditions to maleic acid esters occur with high diastereoselectivity and the products can be converted into highly functionalized pyrrolizidines.

  DOI：

  10.3987/com-08-s(d)59
• 作为产物：
  描述：

  2,3-O-亚异丙基赤藓糖 、 N-苄基羟胺 生成 N-benzyl-N-((3aR,6aR)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)hydroxylamine
  参考文献：
  名称：

  N-Glycosylhydroxylamines as Masked Polyhydroxylated Chiral Nitrones in Cycloaddition Reactions: An Access to Pyrrolizidines

  摘要：

  N-glycosylhydroxylamines undergo 1,3-dipolar cycloadditions via their tautomeric open chain nitrones. Cycloadditions to maleic acid esters occur with high diastereoselectivity and the products can be converted into highly functionalized pyrrolizidines.

  DOI：

  10.3987/com-08-s(d)59

文献信息

• N-Glycosylhydroxylamines as Masked Polyhydroxylated Chiral Nitrones in Cycloaddition Reactions: An Access to Pyrrolizidines
  作者：Andrea Goti、Marco Marradi、Massimo Corsi、Stefano Cicchi、Marco Bonanni、Francesca Cardona

  DOI：10.3987/com-08-s(d)59

  日期：——

  N-glycosylhydroxylamines undergo 1,3-dipolar cycloadditions via their tautomeric open chain nitrones. Cycloadditions to maleic acid esters occur with high diastereoselectivity and the products can be converted into highly functionalized pyrrolizidines.