1-(2-Diazo-acetyl)-1-methyl-spiro[3.5]nonan-2-one | 132156-78-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-Diazo-acetyl)-1-methyl-spiro[3.5]nonan-2-one
• 英文别名: 3-(2-Diazoacetyl)-3-methylspiro[3.5]nonan-2-one
• CAS: 132156-78-6
• 化学式: C₁₂H₁₆N₂O₂
• 分子量: 220.271
• InChiKey: KDOPBKOLFPDCET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  36.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-Diazo-acetyl)-1-methyl-spiro[3.5]nonan-2-one 以 xylene 为溶剂， 反应 0.5h， 以60%的产率得到4-Methyl-1-oxa-dispiro[4.0.5.1]dodec-3-en-2-one
  参考文献：
  名称：

  The generation and rearrangement of 2-(diazoacetyl)cyclobutanones: the formation of 5-spirocyclopropyl-2(5H)-furanones

  摘要：

  We describe here a simple synthesis of 2-(diazoacetyl)cyclobutanones and their facile thermal rearrangement to 5-spirocyclopropyl-DELTA-alpha,beta-butenolides. The yield of the rearrangement product is high, and the reaction is completely stereospecific. alpha-Ketenylcyclobutanones have been identified spectroscopically as intermediates, and their rearrangement was studied kinetically. A strained dipolar cyclic transition is proposed for the rearrangement of the alpha-ketenylcyclobutanones to the corresponding 5-spirocyclopropyl-DELTA-alpha,beta-butenolides.

  DOI：

  10.1021/jo00004a022
• 作为产物：
  描述：

  1-Methyl-2-oxo-spiro[3.5]nonane-1-carboxylic acid 在 草酰氯 作用下， 以 乙醚 为溶剂， 反应 16.0h， 生成 1-(2-Diazo-acetyl)-1-methyl-spiro[3.5]nonan-2-one
  参考文献：
  名称：

  The generation and rearrangement of 2-(diazoacetyl)cyclobutanones: the formation of 5-spirocyclopropyl-2(5H)-furanones

  摘要：

  We describe here a simple synthesis of 2-(diazoacetyl)cyclobutanones and their facile thermal rearrangement to 5-spirocyclopropyl-DELTA-alpha,beta-butenolides. The yield of the rearrangement product is high, and the reaction is completely stereospecific. alpha-Ketenylcyclobutanones have been identified spectroscopically as intermediates, and their rearrangement was studied kinetically. A strained dipolar cyclic transition is proposed for the rearrangement of the alpha-ketenylcyclobutanones to the corresponding 5-spirocyclopropyl-DELTA-alpha,beta-butenolides.

  DOI：

  10.1021/jo00004a022

文献信息

• MILLER, R. D.;THEIS, W.;HEILIG, G.;KIRCHMEYER, S., J. ORG. CHEM., 56,(1991) N, C. 1453-1463
  作者：MILLER, R. D.、THEIS, W.、HEILIG, G.、KIRCHMEYER, S.

  DOI：——

  日期：——