(S)-3-amino-2-(1-hydroxy-2-methylpropyl)quinazolin-4(3H)-one | 329729-35-3

• 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: (S)-3-amino-2-(1-hydroxy-2-methylpropyl)quinazolin-4(3H)-one
• 英文别名: 3-Amino-2-[(S)-1-hydroxy-2-methylpropyl]quinazolin-4(3H)-one；(S)-2-(1-hydroxy-2-methyl)propyl-3-aminoquinazolin-4-one；3-amino-2-[(S)-1-hydroxy-2-methylpropyl]quinazolin-4-(3H)-one；3-amino-2-[(1S)-1-hydroxy-2-methylpropyl]quinazolin-4-one
• CAS: 329729-35-3
• 化学式: C₁₂H₁₅N₃O₂
• 分子量: 233.27
• InChiKey: AJLJHIJQGNMGBW-JTQLQIEISA-N

物化性质

• 沸点：
  415.1±47.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-amino-2-(1-hydroxy-2-methylpropyl)quinazolin-4(3H)-one 在 六甲基二硅氮烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-[(1S)-1-hydroxy-2-methylpropyl]-3-[[oxo(diphenyl)-lambda6-sulfanylidene]amino]quinazolin-4-one
  参考文献：
  名称：

  Synthesis of chiral sulfoximines derived from 3-aminoquinazolinones and their catalysis of enantioselective diethylzinc addition to aldehydes

  摘要：

  一系列亚砜通过铅四醋酸盐的氧化加成反应与3-氨基喹唑啉酮进行硫氧化胺化。在六甲基二硅氮的存在下，它们首次应用于对芳香醛的催化对映选择性加成，在2-甲氧基苯甲醛的情况下，产物的对映体纯度（ee）达到92%。

  DOI：

  10.1039/c1ob06205k
• 作为产物：
  描述：

  Methyl (S)-N-(2-acetoxy-3-methylbutanoyl)anthranilate 在 肼 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以82%的产率得到(S)-3-amino-2-(1-hydroxy-2-methylpropyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Stereoisomerism in 3-[N-(2-acetoxypropanoyl)-N-acylamino]quinazolin-4(3H )-ones, enantioselective acylating agents

  摘要：

  标题化合物二酰氨基喹唑啉酮（DAQs）是针对胺的选择性酰化试剂，针对其立体结构进行了详细研究，以期理解这种对映选择性的来源。这些DAQs中的N-N键是一个手性轴。即使两个N-酰基团都是(S)-2-乙酸基丙酰基，N-N键仍然是一个手性轴，因为在平面亚胺部分的最稳定构象中，一种外-内构象的羰基基团比另一种内-外构象更为优先，NMR光谱学揭示了这一点。2-乙酸基丙酰基团内的构象偏好解释了某些DAQs在溶液中存在单一外-内构象（如上所示），而其他则存在互变的外-内⇌内-外混合物。在溶液中存在单一外-内构象的情况下，提供了证据表明，这种构象与X射线确定的晶体结构非常相似。提出了一种形成这些DAQs的第二步酰化机制，该机制涉及对3-(单酰氨基)喹唑啉酮的初步O-酰化。

  DOI：

  10.1039/b005814i

文献信息

• 3-Aminoquinazoline–phosphine ligands and their ruthenium(II) complexes: application in catalytic hydrogenation and transfer hydrogenation reactions
  作者：Mustafa Kemal Yılmaz、Mustafa Keleş

  DOI：10.1007/s11243-018-0213-9

  日期：2018.4

  and microanalysis. The 3-aminoquinazolinone–phosphine ligands were found to coordinate with the Ru(II) center via their phosphorus and nitrogen atoms. The Ru(II) complexes were applied as catalysts for the hydrogenation and transfer hydrogenation of prochiral ketones. The results showed that these complexes are efficient transfer hydrogenation catalysts.

  摘要 制备了 3-氨基喹唑啉酮-膦前配体 (5a-e) 及其 Ru(II) 配合物 (6a-e)，并通过 NMR（1H、13C、31P1H}）、FTIR 和微量分析对其进行了表征。发现 3-氨基喹唑啉酮-膦配体通过其磷和氮原子与 Ru(II) 中心配位。Ru(II)配合物用作前手性酮加氢和转移加氢的催化剂。结果表明，这些配合物是有效的转移加氢催化剂。
• Synthesis of unsymmetrical 3,3′-biquinazoline-2,2′-diones by condensation of 3-aminoquinazolinones with benzoxazinones; fortuitous discovery, and further syntheses of 4-H-3-oxo-1,9a,10-triazaanthracen-9-ones
  作者：Michael P. Coogan、Li-ling Ooi、Fabrizio Pertusati

  DOI：10.1039/b419108k

  日期：——

  2' disubstituted 3,3' biquinazoline-4,4'-diones. The reaction is tolerant to a range of heteroatom and unsaturated functionality in the quinazolinone 2-position. However, treatment of 3-amino-2-hydroxymethyl-3H-quinazolin-4-ones with benz[1,3]oxazinone at high temperatures gave 4H-3-oxo-1,9a,10-triazaanthracen-9-ones, an unreported fused heterocyclic system, a more direct synthesis of which, replacing

  2-烷基-或2-芳基-3-氨基喹唑啉-4-酮与苯并[1,3]恶嗪-4-酮的缩合产生不对称的2,2'二取代的3,3'联喹唑啉-4,4'-二酮。该反应可耐受喹唑啉酮2位上的一系列杂原子和不饱和官能团。然而，在高温下用苯并[1,3]恶嗪酮处理3-氨基-2-羟甲基-3H-喹唑啉-4-酮，得到4H-3-oxo-1,9a，10-triazaanthracen-9-one。未报道的稠合杂环系统，其更直接的合成方法是用原酸酯代替苯并恶嗪酮。
• Synthesis of 2-Chirally Substituted 3,3′-Biquinazoline-4,4′-diones
  作者：Fabrizio Pertusati、Michael P. Coogan

  DOI：10.1002/jhet.1868

  日期：2014.8

  diastereoisomers, which can be enriched with the major diastereoisomer by simple recrystallization. The functional groups in the lateral chain can be easily modified allowing the synthesis of a variety of 3,3′-biquinazoline-4,4′-diones. The synthesis of symmetrically 2,2′ chirally disubstituted biquinazolinones via acylation/dehydration sequence of bisanthraniloyl hydrazine is also described.

  一种通过手性缩合反应将手性中心并入其侧部附属物中的2-取代联喹唑啉酮的简便方法 描述了具有3-氨基-2 S-取代的喹唑啉-4-酮的4 H -3,1-苯并恶嗪-4-酮。该方法简单明了，不需要在任何阶段进行色谱纯化。以非对映异构体的混合物形式获得高收率的产物，可以通过简单的重结晶使其富含主要的非对映异构体。可以容易地修饰侧链中的官能团，从而允许合成各种3,3'-联喹唑啉-4,4'-二酮。对称的2,2'手性二取代联喹唑啉酮的酰化/脱水序列的合成。还描述了双蒽基酰肼。
• 3-Aminoquinazolinones as chiral ligands in catalytic enantioselective diethylzinc and phenylacetylene addition to aldehydes
  作者：Semistan Karabuga、Idris Karakaya、Sabri Ulukanli

  DOI：10.1016/j.tetasy.2014.04.019

  日期：2014.5

  A series of readily known enantiomerically pure 3-aminoquinazolinones 1a-d were synthesised from easily accessible chiral pool alpha-hydroxy acids and alpha-amino acids in only four steps without any requirement of chromatography. These quinazolinones were examined as chiral ligands for catalytic enantioselective diethylzinc and phenylacetylene additions to aldehydes. For enantioselective alkylations, the effects of temperature, solvent, diethylzinc and ligand criteria were analysed, and the desired chiral alcohols were obtained in up to 86% ee. 3-Aminoquinazolinones 1a-d were also shown to be very useful ligands in enantioselective alkynylations of aldehydes. Based upon the optimised conditions, the corresponding propargylic alcohols were obtained in up to 94% ee. (C) 2014 Elsevier Ltd. All rights reserved.
• 3-(N,N-Diacylamino)quinazolin-4(3H)-ones as enantioselective acylating agents for amines
  作者：Abdullah G Al-Sehemi、Robert S Atkinson、John Fawcett、David R Russell

  DOI：10.1016/s0040-4039(00)00138-6

  日期：2000.3

  The presence of an N-N chiral axis in a 3-(N-benzoyl-N-isobutanoyl)aminoquinazolin-4(3H)-one (DAQ) bearing a chiral substituent in the 2-position of the quinazolinone allows separation of two enantiopure diastereoisomers; one of these diastereoisomers reacts with racemic 2-methylpiperidine to give (R)(+)-1-benzoyl-2-methylpiperidine (95% ee) and (S)-2-methylpiperidine (91% ee) even using stoichiometric quantities of reagents (1 equiv. DAQ: 2 equiv. amine). (C) 2000 Elsevier Science Ltd. All rights reserved.