3-methoxyacetophenone-ethoxycarbonylhydrazone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-methoxyacetophenone-ethoxycarbonylhydrazone
• 英文别名: ethyl N-[(E)-1-(3-methoxyphenyl)ethylideneamino]carbamate
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: KTRXBSXJLGJCOW-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methoxyacetophenone-ethoxycarbonylhydrazone 、 环氧溴丙烷 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 17.33h， 以62%的产率得到2-(3-methoxyphenyl)-3,4,4a,5-tetrahydrooxazolo[3,4-b]pyridazin-7-one
  参考文献：
  名称：

  One-Pot Cyclizations of Dilithiated Oximes and Hydrazones with Epibromohydrin. Efficient Synthesis of 6-Hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and Oxazolo[3,4-b]pyridazin-7-ones

  摘要：

  [GRAPHICS]The one-pot cyclization of dilithiated oximes with epibromohydrin provided a convenient and regioselective approach to 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines. The reaction of the latter with phosphorus tribromide resulted in a Beckmann rearrangement and formation of 5-bromomethyl-2-iminotetrahydrofurans. The reaction of dilithiated hydrazones with epibromohydrin afforded oxazolo[3,4-b]pyridazin-7-ones, which were formed by a novel domino cyclization.

  DOI：

  10.1021/jo052329e
• 作为产物：
  描述：

  肼基甲酸乙酯 、 3-甲氧基苯乙酮 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以38%的产率得到3-methoxyacetophenone-ethoxycarbonylhydrazone
  参考文献：
  名称：

  One-Pot Cyclizations of Dilithiated Oximes and Hydrazones with Epibromohydrin. Efficient Synthesis of 6-Hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and Oxazolo[3,4-b]pyridazin-7-ones

  摘要：

  [GRAPHICS]The one-pot cyclization of dilithiated oximes with epibromohydrin provided a convenient and regioselective approach to 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines. The reaction of the latter with phosphorus tribromide resulted in a Beckmann rearrangement and formation of 5-bromomethyl-2-iminotetrahydrofurans. The reaction of dilithiated hydrazones with epibromohydrin afforded oxazolo[3,4-b]pyridazin-7-ones, which were formed by a novel domino cyclization.

  DOI：

  10.1021/jo052329e

文献信息

• Synthesis of pyrazole-3-carboxylates and pyrazole-1,5-dicarboxylates by one-pot cyclization of hydrazone dianions with diethyl oxalate
  作者：Tung T. Dang、Tuan T. Dang、Christine Fischer、Helmar Görls、Peter Langer

  DOI：10.1016/j.tet.2007.12.024

  日期：2008.2

  The one-pot cyclization of hydrazone dianions with diethyl oxalate allows a convenient synthesis of pyrazole-3-carboxylates and pyrazole-1,5-dicarboxylates.

  与草酸二乙酯的一锅法二价环化反应可以方便地合成吡唑-3-羧酸盐和吡唑-1,5-二羧酸盐。
• One-Pot Cyclizations of Dilithiated Oximes and Hydrazones with Epibromohydrin. Efficient Synthesis of 6-Hydroxymethyl-5,6-dihydro-4<i>H</i>-1,2-oxazines and Oxazolo[3,4-<i>b</i>]pyridazin-7-ones
  作者：Tuan Thanh Dang、Uwe Albrecht、Katrin Gerwien、Melanie Siebert、Peter Langer

  DOI：10.1021/jo052329e

  日期：2006.3.1

  [GRAPHICS]The one-pot cyclization of dilithiated oximes with epibromohydrin provided a convenient and regioselective approach to 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines. The reaction of the latter with phosphorus tribromide resulted in a Beckmann rearrangement and formation of 5-bromomethyl-2-iminotetrahydrofurans. The reaction of dilithiated hydrazones with epibromohydrin afforded oxazolo[3,4-b]pyridazin-7-ones, which were formed by a novel domino cyclization.