(S)-3-amino-2-(hydroxy(phenyl)methyl)quinazolin-4(3H)-one | 850870-20-1

• 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-(hydroxy(phenyl)methyl)quinazolin-4(3H)-one
• 英文别名: 3-amino-2-[(S)-hydroxyphenylmethyl]-4(3H)-quinazolinone；3-amino-2-(phenylhydroxymethyl)quinazolin-4-one；3-amino-2-[1-hydroxybenzyl]-quinazolin-(3H0-4-one；3-amino-2-[(S)-hydroxy(phenyl)methyl]quinazolin-4-one
• CAS: 850870-20-1
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: JCZWLJUUXNUJJM-ZDUSSCGKSA-N

物化性质

• 熔点：
  139 °C(Solv: ethanol (64-17-5))
• 沸点：
  499.6±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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-(hydroxy(phenyl)methyl)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-[(S)-hydroxy(phenyl)methyl]-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：

  (S)-2-氯-2-氧代-1-苯基乙基乙酸酯 在 一水合肼 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 8.0h， 生成 (S)-3-amino-2-(hydroxy(phenyl)methyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  通过3-氨基喹唑啉酮与苯并恶嗪酮的缩合反应合成不对称的3,3'-联喹唑啉-2,2'-二酮；偶然发现，并进一步合成4-H-3-oxo-1,9a，10-triazaanthracen-9-ones。

  摘要：

  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。

  DOI：

  10.1039/b419108k
• 作为试剂：
  描述：

  diethylzinc 、 苯甲醛 在 (S)-3-amino-2-(hydroxy(phenyl)methyl)quinazolin-4(3H)-one 作用下， 以 甲苯 为溶剂， 以67%的产率得到1-苯丙醇
  参考文献：
  名称：

  3-Aminoquinazolinones as chiral ligands in catalytic enantioselective diethylzinc and phenylacetylene addition to aldehydes

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2014.04.019

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 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.
• Synthesis of chiral sulfoximines derived from 3-aminoquinazolinones and their catalysis of enantioselective diethylzinc addition to aldehydes
  作者：Semistan Karabuga、Murat Cakici、Cavit Kazaz、Ertan Sahin、Hamdullah Kilic、Sabri Ulukanli

  DOI：10.1039/c1ob06205k

  日期：——

  A series of sulfoxides were sulfoximinated using oxidative addition of 3-aminoquinazolinones by lead tetraacetate in the presence of hexamethyldisilazane. They were applied for the first time in catalytic enantioselective addition to aromatic aldehydes with a product enantiopurity (ee) of 92% in the case of 2-methoxybenzaldehyde.

  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%。
• 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。