N-(2-ethyl-4-oxoquinazolin-3-yl)-N-[(Z)-3-hydroxybut-2-en-2-yl]acetamide | 144522-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(2-ethyl-4-oxoquinazolin-3-yl)-N-[(Z)-3-hydroxybut-2-en-2-yl]acetamide
• CAS: 144522-62-3
• 化学式: C₁₆H₁₉N₃O₃
• 分子量: 301.345
• InChiKey: ZXXJHQYXNYCIAV-KHPPLWFESA-N

物化性质

• 沸点：
  452.7±51.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-ethyl-4-oxoquinazolin-3-yl)-N-[(Z)-3-hydroxybut-2-en-2-yl]acetamide 在 三氟化硼乙醚 、 烯丙基三甲基硅烷 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 0.02h， 生成 N-(1-亚甲基-2-氧代丙基)-乙酰胺
  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
• 作为产物：
  描述：

  3-(acetoxyamino)-2-ethylquinazolin-4(3H)-one 、 4-hydroxy-3-methylpent-3-en-2-one 以 二氯甲烷 为溶剂， 以66%的产率得到N-(2-ethyl-4-oxoquinazolin-3-yl)-N-[(Z)-3-hydroxybut-2-en-2-yl]acetamide
  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

• Asymmetric induction mediated by an N–N chiral axis
  作者：Robert S. Atkinson、Paul J. Edwards、Gordon A. Thomson

  DOI：10.1039/c39920001256

  日期：——

  Reaction of 3-methylpentane-2,4-dione 11 with N-acetoxyaminoquinazolinone 6 gives an isolable enol 12, which is chiral by virtue of the high barrier to rotation around its N–N bond; protonation of the double bond occurs in glacial acetic acid to give a single diastereoisomer of keto-amide 13.

  3- 甲基戊烷-2,4-二酮 11 与 N- 乙酰氧基氨基喹唑啉酮 6 反应生成可分离的烯醇 12，由于其 NâN 键周围的旋转障碍较高，因此具有手性；双键在冰乙酸中发生质子化反应，生成酮酰胺 13 的单一非对映异构体。
• 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.