methyl (E)-4-(dimethylhydrazono)crotonate | 909393-39-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (E)-4-(dimethylhydrazono)crotonate
• 英文别名: Methyl-(e)-4-dimethylhydrazono-2-butenoate；methyl (E,4E)-4-(dimethylhydrazinylidene)but-2-enoate
• CAS: 909393-39-1
• 化学式: C₇H₁₂N₂O₂
• 分子量: 156.184
• InChiKey: GINJHZMIRUSPAD-DVBIZMGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(phenylsulfonyl)-1,4-benzoquinone monoimine 、 methyl (E)-4-(dimethylhydrazono)crotonate 以 乙醇 为溶剂， 反应 5.5h， 以32%的产率得到(4bR,5S,10aS)-3-Benzenesulfonylamino-9-[(E)-benzenesulfonylimino]-10-dimethylamino-6-oxo-4b,5,5a,6,9,9a,10,10a-octahydro-11-oxa-10-aza-benzo[b]fluorene-5-carboxylic acid methyl ester
  参考文献：
  名称：

  [3+2] versus [4+2] Cycloadditions of Quinone Monoimide with Azadienes:  A Lewis Acid-Free Access to 5-Amino-2,3-dihydrobenzofuranes

  摘要：

  The reaction between p-quinone monoimide 1a and various azadienes 2 is described in the absence of a Lewis acid promoter. When alpha,beta-unsaturated hydrazones are substituted by proton or alkyl groups, 2,3-dihydrobenzofuranes 4, a motif that is present in numerous biologically active products, are obtained in moderate to excellent yields. The regio- and stereoselectivity of this reaction has been proved by a complete NMR study, including H-1-N-15 correlations.

  DOI：

  10.1021/ol061184a
• 作为产物：
  描述：

  methyl (E)-2-(1,1-dimethyl-1,2-diazabutadien-4-ylidene)malonate 生成 methyl (E)-4-(dimethylhydrazono)crotonate
  参考文献：
  名称：

  LYONS J. J.; MCNAB H., J. CHEM. SOC. PERKIN TRANS.,(1987) N 3, 649-652

  摘要：

  DOI：

文献信息

• Lyons, Jacqueline J.; McNab, Hamish, Journal of the Chemical Society. Perkin transactions I, 1987, p. 649 - 652
  作者：Lyons, Jacqueline J.、McNab, Hamish

  DOI：——

  日期：——
• LYONS J. J.; MCNAB H., J. CHEM. SOC. PERKIN TRANS.,(1987) N 3, 649-652
  作者：LYONS J. J.、 MCNAB H.

  DOI：——

  日期：——
• [3+2] versus [4+2] Cycloadditions of Quinone Monoimide with Azadienes:  A Lewis Acid-Free Access to 5-Amino-2,3-dihydrobenzofuranes
  作者：Thierry Lomberget、Fabien Baragona、Bernard Fenet、Roland Barret

  DOI：10.1021/ol061184a

  日期：2006.8.1

  The reaction between p-quinone monoimide 1a and various azadienes 2 is described in the absence of a Lewis acid promoter. When alpha,beta-unsaturated hydrazones are substituted by proton or alkyl groups, 2,3-dihydrobenzofuranes 4, a motif that is present in numerous biologically active products, are obtained in moderate to excellent yields. The regio- and stereoselectivity of this reaction has been proved by a complete NMR study, including H-1-N-15 correlations.