2-(1-methylethyl)-3-[(ethoxycarbonyl)methyl]quinazolin-4-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(1-methylethyl)-3-[(ethoxycarbonyl)methyl]quinazolin-4-one
• 英文别名: Ethyl 2-(4-oxo-2-propan-2-ylquinazolin-3-yl)acetate
• 化学式: C₁₅H₁₈N₂O₃
• 分子量: 274.32
• InChiKey: BNNOYJNPUKVFTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-methylethyl)-3-[(ethoxycarbonyl)methyl]quinazolin-4-one 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以75%的产率得到2-(1-methylethyl)-3-[(hydrazinocarbonyl)methyl]quinazolin-4-one
  参考文献：
  名称：

  El-Hashash; Rizk, Egyptian Journal of Chemistry, 2011, vol. 54, # 4, p. 411 - 422

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基2-(2-甲基丙酰氨基)苯甲酸酯 在 sodium hydride 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 67.0h， 生成 2-(1-methylethyl)-3-[(ethoxycarbonyl)methyl]quinazolin-4-one
  参考文献：
  名称：

  Reaction of 3-(acetoxyamino)quinazolin-4(3H)-ones with enolic β-diketones: the N–N bond as a chiral axis in N-(3,4-dihydro-4-oxoquinazolin-3-yl)-N-acyl-α-aminoketones; reductive and base-catalysed cleavage of the N–N bond in N-acetyl-N-(3,4-dihydro-4-oxoquinazolin-3-yl)-α-amino acid esters

  摘要：

  Following the method of Foucaud and coworkers, reaction of pentane-2,4-dione with 3-(acetoxy-amino)quinazolin-4-one 8 gave the keto amide 9 (15%). 3-Methylpentane-2,4-dione reacts with compound 8 to give a relatively stable enol 11 (66%) which can be isolated in a crystalline form. Rotation around the N-N bonds in both compounds 9 and 11 is believed to be slow on the real time-scale and hence the N-N bonds can be considered as a chiral axes. As a result, protonation of the enol double bond in compound 11 and the creation of an additional chiral centre, gives rise to the separable keto amides 14 and 15; this protonation can be accomplished completely diastereoselectively. Lead tetraacetate acetoxylation of compound 11 to give compound 19 is also completely diastereoselective, Brief heating of the enol effects the elimination of the quinazolinone and the formation of the N-acetylimine 16 via an 8-membered transition state. Base-catalysed elimination of the quinazolinone ring from compound 22 is surprisingly easy: reductive cleavage of this N-N bond in compound 22 is facile by comparison with the 3-(alkylamino)quinazolin-4-ones.

  DOI：

  10.1039/p19940003209

文献信息

• Reaction of 3-(acetoxyamino)quinazolin-4(3H)-ones with enolic β-diketones: the N–N bond as a chiral axis in N-(3,4-dihydro-4-oxoquinazolin-3-yl)-N-acyl-α-aminoketones; reductive and base-catalysed cleavage of the N–N bond in N-acetyl-N-(3,4-dihydro-4-oxoquinazolin-3-yl)-α-amino acid esters
  作者：Robert S. Atkinson、Paul J. Edwards、Gordon A. Thomson

  DOI：10.1039/p19940003209

  日期：——

  Following the method of Foucaud and coworkers, reaction of pentane-2,4-dione with 3-(acetoxy-amino)quinazolin-4-one 8 gave the keto amide 9 (15%). 3-Methylpentane-2,4-dione reacts with compound 8 to give a relatively stable enol 11 (66%) which can be isolated in a crystalline form. Rotation around the N-N bonds in both compounds 9 and 11 is believed to be slow on the real time-scale and hence the N-N bonds can be considered as a chiral axes. As a result, protonation of the enol double bond in compound 11 and the creation of an additional chiral centre, gives rise to the separable keto amides 14 and 15; this protonation can be accomplished completely diastereoselectively. Lead tetraacetate acetoxylation of compound 11 to give compound 19 is also completely diastereoselective, Brief heating of the enol effects the elimination of the quinazolinone and the formation of the N-acetylimine 16 via an 8-membered transition state. Base-catalysed elimination of the quinazolinone ring from compound 22 is surprisingly easy: reductive cleavage of this N-N bond in compound 22 is facile by comparison with the 3-(alkylamino)quinazolin-4-ones.
• El-Hashash; Rizk, Egyptian Journal of Chemistry, 2011, vol. 54, # 4, p. 411 - 422
  作者：El-Hashash、Rizk

  DOI：——

  日期：——