3-乙酰基氨基-2-异丙基-4(3H)-喹唑啉酮 | 144522-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-乙酰基氨基-2-异丙基-4(3H)-喹唑啉酮
• 中文别名: 3-乙酰氨基-2-异丙基-4(3H)-喹唑啉酮
• 英文名称: 3-acetylamino-2-isopropylquinazolin-4(3H)-one
• 英文别名: 3-Acetylamino-2-isopropyl-4(3H)-quinazolinone；N-(4-oxo-2-propan-2-ylquinazolin-3-yl)acetamide
• CAS: 144522-58-7
• 化学式: C₁₃H₁₅N₃O₂
• 分子量: 245.281
• InChiKey: IABUZCGOUHAHQF-UHFFFAOYSA-N

物化性质

• 熔点：
  145-149 °C(lit.)
• 稳定性/保质期：

  常温常压下稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  T
• 安全说明：
  S36
• 危险类别码：
  R25
• 海关编码：
  2933990090
• 危险品运输编号：
  UN 2811 6.1/PG 3
• 储存条件：
  密封保存，应储存在阴凉干燥的仓库中。

反应信息

• 作为反应物：
  描述：

  3-乙酰基氨基-2-异丙基-4(3H)-喹唑啉酮 在 aluminium amalgam 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 51.0h， 生成 4-羟基-2-异丙基喹唑啉
  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-氨基-2-异丙基-4(3H)-喹唑啉酮 在 吡啶 、 亚精胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-乙酰基氨基-2-异丙基-4(3H)-喹唑啉酮
  参考文献：
  名称：

  N-acetyl-N-acyl-3-aminoquinazolinones as chemoselective acetylating agents

  摘要：

  标题化合物（例如3）在存在于二级胺的情况下，对一级胺具有高度选择性的乙酰化试剂，特别对于两种不同的二级胺中较少空间位阻的那一种。

  DOI：

  10.1039/cc9960001051

文献信息

• 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，
• 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。
• The N–N bond as a chiral axis: 3-(diacylamino)quinazolin-4(3H)ones as chiral acylating agents
  作者：Robert S. Atkinson、Emma Barker、Christopher J. Price、David R. Russell

  DOI：10.1039/c39940001159

  日期：——

  Two diasteroisomers of 3-(diacylamino)quinazolinone 5 are separated and identified by crystal structure determinations which confirm the presence of an N–N chiral axis: one diastereoisomer of enantiopure 8 reacts with racemic 1-phenylethylamine exclusively at the 2-acetoxypropanoyl imide carbonyl group and with kinetic resolution to give a 3.6 : 1 ratio of diastereoisomers of 10.

  通过晶体结构测定，确认了 NâN 手性轴的存在，从而分离并识别出 3-（二酰氨基）喹唑啉酮 5 的两种非对映异构体：其中一种非对映异构体 8 与外消旋 1-苯基乙胺反应，只在 2-乙酰氧基丙酰亚胺羰基上发生反应，并通过动力学解析得到非对映异构体 10，比例为 3.6:1。
• 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.
• Atkinson, Robert S.; Barker, Emma; Ulukanli, Sabri, Journal of the Chemical Society. Perkin transactions I, 1998, # 3, p. 583 - 589
  作者：Atkinson, Robert S.、Barker, Emma、Ulukanli, Sabri

  DOI：——

  日期：——