3-hydroxymethyl-4-nitrofuroxan

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-hydroxymethyl-4-nitrofuroxan
• 英文别名: (4-nitro-2-oxido-1,2,5-oxadiazol-2-ium-3-yl)methanol
• 化学式: C₃H₃N₃O₅
• 分子量: 161.074
• InChiKey: KLIXEHZYWKGKMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-hydroxymethyl-4-nitrofuroxan 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以51%的产率得到3-chloromethyl-4-nitrofuroxan
  参考文献：
  名称：

  ?-hydroaxyalkyl(benzyl)furozans and ?-hydroxyalkyl(benzyl)furoxans synthesis and reactivity

  摘要：

  A general,and simple preparative method for the synthesis of alpha-hydroxyalkyl(benzyI)furazan and -furoxan derivatives is proposed. The method involves reduction of acyl or ethoxycarbonyl substituents in these heterocyclic compounds with NaBH4 in ethanol. Based on the alcohols thus prepared, a number of previously unknown functional derivatives (alpha-nitroxyalkyl-,alpha-haloalkyl-, and alpha-azidoalkylfurazans and -furoxans) have been synthesized.

  DOI：

  10.1007/bf01431809
• 作为产物：
  描述：

  4-amino-3-hydroxymethylfuroxan 在 硫酸 、 双氧水 作用下， 反应 1.0h， 以81%的产率得到3-hydroxymethyl-4-nitrofuroxan
  参考文献：
  名称：

  ?-hydroaxyalkyl(benzyl)furozans and ?-hydroxyalkyl(benzyl)furoxans synthesis and reactivity

  摘要：

  A general,and simple preparative method for the synthesis of alpha-hydroxyalkyl(benzyI)furazan and -furoxan derivatives is proposed. The method involves reduction of acyl or ethoxycarbonyl substituents in these heterocyclic compounds with NaBH4 in ethanol. Based on the alcohols thus prepared, a number of previously unknown functional derivatives (alpha-nitroxyalkyl-,alpha-haloalkyl-, and alpha-azidoalkylfurazans and -furoxans) have been synthesized.

  DOI：

  10.1007/bf01431809

文献信息

• ?-hydroaxyalkyl(benzyl)furozans and ?-hydroxyalkyl(benzyl)furoxans synthesis and reactivity
  作者：A. N. Blinnikov、S. Kulikov、N. N. Makhova、L. I. Khmel'nitskii

  DOI：10.1007/bf01431809

  日期：1996.7

  A general,and simple preparative method for the synthesis of alpha-hydroxyalkyl(benzyI)furazan and -furoxan derivatives is proposed. The method involves reduction of acyl or ethoxycarbonyl substituents in these heterocyclic compounds with NaBH4 in ethanol. Based on the alcohols thus prepared, a number of previously unknown functional derivatives (alpha-nitroxyalkyl-,alpha-haloalkyl-, and alpha-azidoalkylfurazans and -furoxans) have been synthesized.