cyclopropyl methyl ketone 4-nitrophenylhydrazone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cyclopropyl methyl ketone 4-nitrophenylhydrazone
• 英文别名: N-(1-cyclopropylethylideneamino)-4-nitroaniline
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: JHNXFWFFOXWXJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cyclopropyl methyl ketone 4-nitrophenylhydrazone 在 碘化铵 作用下， 以 邻二氯苯 为溶剂， 反应 4.0h， 以31%的产率得到3-methyl-1-(4-nitrophenyl)-1,4,5,6-tetrahydropyridazine
  参考文献：
  名称：

  The rearrangement of cyclopropylketone arylhydrazones. Synthesis of tryptamines and tetrahydropyridazines

  摘要：

  The cyclopropyliminium rearrangement of cyclopropylketone arylhydrazones may result in two possible products. The first one forms via cyclopropane ring-opening and ring-closure to give six-membered tetrahydropyridazines. The second is formed via ring-closure resulting in a five-membered ring and subsequent Grandberg rearrangement into a tryptamine. The product ratio depends on the nature of the starting hydrazones. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.017
• 作为产物：
  描述：

  环丙甲基酮 、 4-硝基苯肼 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以71%的产率得到cyclopropyl methyl ketone 4-nitrophenylhydrazone
  参考文献：
  名称：

  The rearrangement of cyclopropylketone arylhydrazones. Synthesis of tryptamines and tetrahydropyridazines

  摘要：

  The cyclopropyliminium rearrangement of cyclopropylketone arylhydrazones may result in two possible products. The first one forms via cyclopropane ring-opening and ring-closure to give six-membered tetrahydropyridazines. The second is formed via ring-closure resulting in a five-membered ring and subsequent Grandberg rearrangement into a tryptamine. The product ratio depends on the nature of the starting hydrazones. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.017

文献信息

• The rearrangement of cyclopropylketone arylhydrazones. Synthesis of tryptamines and tetrahydropyridazines
  作者：Rinat F. Salikov、Aleksandr Yu. Belyy、Yury V. Tomilov

  DOI：10.1016/j.tetlet.2014.09.017

  日期：2014.10

  The cyclopropyliminium rearrangement of cyclopropylketone arylhydrazones may result in two possible products. The first one forms via cyclopropane ring-opening and ring-closure to give six-membered tetrahydropyridazines. The second is formed via ring-closure resulting in a five-membered ring and subsequent Grandberg rearrangement into a tryptamine. The product ratio depends on the nature of the starting hydrazones. (C) 2014 Elsevier Ltd. All rights reserved.