2-(3-chloropropoxy)-5-nitropyridine

• 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: 2-(3-chloropropoxy)-5-nitropyridine
• 化学式: C₈H₉ClN₂O₃
• 分子量: 216.624
• InChiKey: FYUMUEHHXPTSOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-chloropropoxy)-5-nitropyridine 以 氘代二甲亚砜 为溶剂， 生成 1-(3-Chloro-propyl)-5-nitro-1H-pyridin-2-one
  参考文献：
  名称：

  Rearrangement of 2-(haloalkoxy)pyridines to N-haloalkyl-2(1H)-pyridones

  摘要：

  2-(Haloalkoxy)pyridines thermally rearrange to N-haloalkyl-2(1H)-pyridones in high Yield. The reaction rate is accelerated by use of a more polar solvent, by bromine rather than chlorine as the halogen substituent and by a two-carbon alkoxy chain as opposed to a three or, especially, four-carbon chain. The reaction kinetics can be interpreted in terms of an oxazolium ion intermediate.

  DOI：

  10.1016/s0040-4039(00)61675-1
• 作为产物：
  描述：

  2-氯-5-硝基吡啶 、 3-氯-1-丙醇 在 sodium hydroxide 、 adogen 464 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以80%的产率得到2-(3-chloropropoxy)-5-nitropyridine
  参考文献：
  名称：

  Rearrangement of 2-(haloalkoxy)pyridines to N-haloalkyl-2(1H)-pyridones

  摘要：

  2-(Haloalkoxy)pyridines thermally rearrange to N-haloalkyl-2(1H)-pyridones in high Yield. The reaction rate is accelerated by use of a more polar solvent, by bromine rather than chlorine as the halogen substituent and by a two-carbon alkoxy chain as opposed to a three or, especially, four-carbon chain. The reaction kinetics can be interpreted in terms of an oxazolium ion intermediate.

  DOI：

  10.1016/s0040-4039(00)61675-1

文献信息

• Rearrangement of 2-(haloalkoxy)pyridines to N-haloalkyl-2(1H)-pyridones
  作者：John C. Schmidhauser、Farid F. Khouri

  DOI：10.1016/s0040-4039(00)61675-1

  日期：1993.10

  2-(Haloalkoxy)pyridines thermally rearrange to N-haloalkyl-2(1H)-pyridones in high Yield. The reaction rate is accelerated by use of a more polar solvent, by bromine rather than chlorine as the halogen substituent and by a two-carbon alkoxy chain as opposed to a three or, especially, four-carbon chain. The reaction kinetics can be interpreted in terms of an oxazolium ion intermediate.