3-(1-adamantyl)-1H-pyrazol-5-one | 496938-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 3-(1-adamantyl)-1H-pyrazol-5-one
• 英文别名: 3-(1-adamantyl)-4,5-dihydro-1H-pyrazol-5-one；3-(1-adamantyl)-1,4-dihydropyrazol-5-one
• CAS: 496938-13-7
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: OMPKDBCILMAIBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1-adamantyl)-1H-pyrazol-5-one 在 溶剂黄146 、 sodium nitrite 作用下， 反应 3.0h， 以96%的产率得到3-(1-adamantyl)-4-hydroxyimino-4,5-dihydro-1H-pyrazol-5-one
  参考文献：
  名称：

  Synthesis and Some Chemical Transformations of Adamantyl-Substituted Pyrazolones

  摘要：

  1-Substituted 3-(1-adamantyl)-4,5-dihydro-1H-pyrazol-5-ones and 3-(1-adamantyl)-4,5-dihydroiso-xazol-5-one were synthesized by reaction of ethyl 3-(1-adamantyl)-3-oxopropanoate with various hydrazine derivatives and hydroxylamine hydrochloride. Nitrosation of adamantyl-substituted pyrazolones with sodium nitrite in acetic acid gave the corresponding 4-hydroxyimino derivatives. Reactions of 3-(1-adamantyl)-4,5-di-hydro-1H-pyrazol-5-ones and 3-(1-adamantyl)-4,5-dihydroisoxazol-5-one with aromatic and heterocyclic aldehydes led to the formation of condensation products at position 4 of the heteroring.

  DOI：

  10.1134/s1070428010100209
• 作为产物：
  描述：

  3-(1-金刚烷)-3-氧代丙酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 以63%的产率得到3-(1-adamantyl)-1H-pyrazol-5-one
  参考文献：
  名称：

  金刚烷基取代的酮酯与肼和苯肼的反应

  摘要：

  Reactions of adamantyl-substituted keto and diketo carboxylic acid esters with hydrazine and phenylhydrazine were studied. Ethyl 3-(1-adamantyl)-2-(1-adamantylcarbonyl)-3-oxopropanoate reacted with hydrazine to give ethyl 3,5-di(1-adamantyl)-1H-pyrazole-4-carboxylate. Reactions of ethyl 2-(1-adamantylcarbonyl)-3-oxobutanoate and ethyl 4-(1-adamantyl)-3-oxo-2-(1-oxoethyl)butanoate with hydrazine and phenylhydrazine followed a complicated pattern and led to the formation of mixtures of the corresponding hydrazides and pyrazolones.

  DOI：

  10.1134/s1070428008120063

文献信息

• Reactions of adamantyl-substituted keto esters with hydrazine and phenylhydrazine
  作者：K. M. Bormasheva、O. N. Nechaeva、I. K. Moiseev

  DOI：10.1134/s1070428008120063

  日期：2008.12

  Reactions of adamantyl-substituted keto and diketo carboxylic acid esters with hydrazine and phenylhydrazine were studied. Ethyl 3-(1-adamantyl)-2-(1-adamantylcarbonyl)-3-oxopropanoate reacted with hydrazine to give ethyl 3,5-di(1-adamantyl)-1H-pyrazole-4-carboxylate. Reactions of ethyl 2-(1-adamantylcarbonyl)-3-oxobutanoate and ethyl 4-(1-adamantyl)-3-oxo-2-(1-oxoethyl)butanoate with hydrazine and phenylhydrazine followed a complicated pattern and led to the formation of mixtures of the corresponding hydrazides and pyrazolones.
• Synthesis and Some Chemical Transformations of Adamantyl-Substituted Pyrazolones
  作者：K. M. Bormasheva、S. A. Kon’kov、I. K. Moiseev

  DOI：10.1134/s1070428010100209

  日期：2010.10

  1-Substituted 3-(1-adamantyl)-4,5-dihydro-1H-pyrazol-5-ones and 3-(1-adamantyl)-4,5-dihydroiso-xazol-5-one were synthesized by reaction of ethyl 3-(1-adamantyl)-3-oxopropanoate with various hydrazine derivatives and hydroxylamine hydrochloride. Nitrosation of adamantyl-substituted pyrazolones with sodium nitrite in acetic acid gave the corresponding 4-hydroxyimino derivatives. Reactions of 3-(1-adamantyl)-4,5-di-hydro-1H-pyrazol-5-ones and 3-(1-adamantyl)-4,5-dihydroisoxazol-5-one with aromatic and heterocyclic aldehydes led to the formation of condensation products at position 4 of the heteroring.