3-(2,2-Dimethylpropanoyl)amino-2-isopropyl-3,4-dihydroquinazolin-4-one | 173371-71-6

• 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: 3-(2,2-Dimethylpropanoyl)amino-2-isopropyl-3,4-dihydroquinazolin-4-one
• 英文别名: 2-(1-methylethyl)-3-(pivaloylamino)-4(3H)-quinazolinone；2,2-dimethyl-N-(4-oxo-2-propan-2-ylquinazolin-3-yl)propanamide
• CAS: 173371-71-6
• 化学式: C₁₆H₂₁N₃O₂
• 分子量: 287.362
• InChiKey: IADRLAROKPYSFF-UHFFFAOYSA-N

物化性质

• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2,2-Dimethylpropanoyl)amino-2-isopropyl-3,4-dihydroquinazolin-4-one 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以75%的产率得到3-氨基-2-异丙基-4(3H)-喹唑啉酮
  参考文献：
  名称：

  3-（酰基氨基）-2-未取代的，3-（酰基氨基）-2-乙基-和3-（酰基氨基）-2-丙基-4（3H）-喹唑啉酮的锂化反应：更复杂的喹唑啉酮的简便合成方法（1 ）。

  摘要：

  3-（新戊酰氨基）-和3-（乙酰氨基）-4（3H）-喹唑啉酮类与烷基锂试剂反应生成1,2-加成产物，收率很高。用LDA进行锂化并且在2位上具有区域选择性。由此获得的锂试剂与各种亲电试剂反应，以非常好的收率得到相应的取代衍生物。锂试剂与碘的反应产生氧化二聚的环状结构。3-（新戊酰氨基）-和3-（乙酰氨基）-2-乙基-4（3H）-喹唑啉酮和3-（新戊酰氨基）-和3-（乙酰氨基）-2-丙基-4（3H）-喹唑啉酮在LDA的苄基位置。如此产生的锂试剂还与多种亲电试剂反应，以非常好的收率得到相应的2-取代的-4（3H）-喹唑啉酮衍生物。然而，

  DOI：

  10.1021/jo950988t
• 作为产物：
  描述：

  三甲基乙酸 在 吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-(2,2-Dimethylpropanoyl)amino-2-isopropyl-3,4-dihydroquinazolin-4-one
  参考文献：
  名称：

  The N–N bond as a chiral axis: 3-diacylaminoquinazolinones as chiral acylating agents

  摘要：

  3-Diacylaminoquinazolinones 10 and 15 have high enough barriers to rotation around their N-N bonds to allow separation of each into diastereoisomers. Interconversion of diastereoisomers 10a and 10b occurs on heating in boiling toluene and thermodynamic parameters for this process have been measured, The barriers to rotation around the N-N bonds in analogous monoacylaminoquinazolinones are not sufficient to permit isolation of stereoisomers at room temperature unless the exocyclic nitrogen is additionally substituted e.g. by an alkyl group as in 28, X-Ray crystal structure determinations carried out on 10a, 10b, 15a and 28b confirm the presence of chiral axes, Reaction of both diastereoisomers 15a and 15b with 1-phenylethylamine takes place with exclusive reaction at the 1-acetoxypropionyl carbonyl group and with partial kinetic resolution: the preferred sense of enantioselectivity obtained is dominated by the N-N axis.

  DOI：

  10.1039/p19960001047

文献信息

• The N–N bond as a chiral axis: 3-diacylaminoquinazolinones as chiral acylating agents
  作者：Robert S. Atkinson、Emma Barker、Paul J. Edwards、Gordon A. Thomson

  DOI：10.1039/p19960001047

  日期：——

  3-Diacylaminoquinazolinones 10 and 15 have high enough barriers to rotation around their N-N bonds to allow separation of each into diastereoisomers. Interconversion of diastereoisomers 10a and 10b occurs on heating in boiling toluene and thermodynamic parameters for this process have been measured, The barriers to rotation around the N-N bonds in analogous monoacylaminoquinazolinones are not sufficient to permit isolation of stereoisomers at room temperature unless the exocyclic nitrogen is additionally substituted e.g. by an alkyl group as in 28, X-Ray crystal structure determinations carried out on 10a, 10b, 15a and 28b confirm the presence of chiral axes, Reaction of both diastereoisomers 15a and 15b with 1-phenylethylamine takes place with exclusive reaction at the 1-acetoxypropionyl carbonyl group and with partial kinetic resolution: the preferred sense of enantioselectivity obtained is dominated by the N-N axis.
• Lithiation of 3-(Acylamino)-2-unsubstituted-, 3-(Acylamino)-2-ethyl-, and 3-(Acylamino)-2-propyl-4(3<i>H</i>)-quinazolinones:  Convenient Syntheses of More Complex Quinazolinones¹
  作者：Keith Smith、Gamal A. El-Hiti、Mohamed F. Abdel-Megeed、Mohamed A. Abdo

  DOI：10.1021/jo950988t

  日期：1996.1.1

  3-(acetylamino)-2-ethyl-4(3H)-quinazolinones and 3-(pivaloylamino)- and 3-(acetylamino)-2-propyl-4(3H)-quinazolinones are lithiated at the benzylic position with LDA. The lithium reagents so produced also react with a variety of electrophiles to give the corresponding 2-substituted-4(3H)-quinazolinone derivatives in very good yields. However, lithiation of 3-(acylamino)-2-(1-methylethyl)-4(3H)-quinazolinones was unsuccessful

  3-（新戊酰氨基）-和3-（乙酰氨基）-4（3H）-喹唑啉酮类与烷基锂试剂反应生成1,2-加成产物，收率很高。用LDA进行锂化并且在2位上具有区域选择性。由此获得的锂试剂与各种亲电试剂反应，以非常好的收率得到相应的取代衍生物。锂试剂与碘的反应产生氧化二聚的环状结构。3-（新戊酰氨基）-和3-（乙酰氨基）-2-乙基-4（3H）-喹唑啉酮和3-（新戊酰氨基）-和3-（乙酰氨基）-2-丙基-4（3H）-喹唑啉酮在LDA的苄基位置。如此产生的锂试剂还与多种亲电试剂反应，以非常好的收率得到相应的2-取代的-4（3H）-喹唑啉酮衍生物。然而，