(S)-3-amino-2-(1-hydroxyethyl)quinazolin-4(3H)-one | 141236-01-3

• 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-hydroxyethyl)quinazolin-4(3H)-one
• 英文别名: 3-amino-2-[(1S)-1-hydroxyethyl]quinazolin-4-one
• CAS: 141236-01-3
• 化学式: C₁₀H₁₁N₃O₂
• 分子量: 205.216
• InChiKey: FPACNLGMCYTJIL-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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-hydroxyethyl)quinazolin-4(3H)-one 在 咪唑 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.08h， 生成 2-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-3-[(2S,3S)-2-phenyl-3-trimethylsilylaziridin-1-yl]quinazolin-4-one
  参考文献：
  名称：

  Desilylative elimination of the quinazolinone ring from 1-(4-oxoquinazolin-3-yl)-2-silylaziridines; preparation of an N–H aziridine in high enantiomeric excess by in situ nucleophilic addition to the derived azirine

  摘要：

  乙烯基硅烷的氮丙啶化 PhCHCHSiR3 (R = Me, Et, Ph) 与 对映体纯 3-乙酰氧基氨基喹唑啉酮 11 给出 相应的氮丙啶 12 [非对映异构体比例 (dr) 10-1]、18（13-1 博士）和 20（2-1 博士）。 从这些物质中脱甲硅烷基消除喹唑啉酮 在氰化物存在下与氟化铯反应生成氮丙啶 氮丙啶 14 通过氰化物加成到 3-未取代的氮丙啶上 13、原地制作。氮丙啶 14 的酰化 (S)-乙酰氧基丙酰氯得到 N-酰基氮丙啶16；之间的良好相关性 氮丙啶 12、18 和 20 的非对映异构体比例 每种情况下产生的 N-酰基氮丙啶 16 表明 中间体氮丙啶 13 在构型上是 稳定的。

  DOI：

  10.1039/a606092g
• 作为产物：
  描述：

  methyl 2-acetoxypropanoylanthranilate 在 肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以81%的产率得到(S)-3-amino-2-(1-hydroxyethyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  用3-乙酰氧基氨基喹唑啉-4-（3h）酮进行胺化：通过与甲硅烷基烯酮缩醛反应，然后裂解NN键，制备α-氨基酸酯

  摘要：

  3-乙酰氧基氨基喹唑啉酮（5）的溶液与烯醇醚和甲硅烷基乙烯酮缩醛反应，得到α-氨基醛α-氨基酮或α-氨基酸衍生物。这些衍生物中环外氮的酰化，作为还原性NN键断裂的先决条件，只能通过间接方式完成。然而，二碘化可实现NN键的还原，而无需进行N-酰化。相应的对映体纯的3-乙酰氧基氨基喹唑啉酮（34）的溶液引起前手性甲硅烷基乙烯酮缩醛（15）的非对映选择性胺化，以及主要非对映异构体的还原性NN键裂解导致对映纯2-苯丙氨酸甲酯。

  DOI：

  10.1016/s0040-4020(01)90382-5
• 作为试剂：
  描述：

  苯乙炔 、 邻甲氧基苯甲醛 在 titanium(IV) isopropylate 、 (S)-3-amino-2-(1-hydroxyethyl)quinazolin-4(3H)-one 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以88%的产率得到
  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。
• Aziridination of β-substituted styrene derivatives with 3-acetoxyaminoquinazolin-4(3H)-ones: probing transition state geometry from changes in diastereoselectivity
  作者：Robert S. Atkinson、John Fawcett、Ian S. T. Lochrie、Sabri Ulukanli、Thomas A. Claxton

  DOI：10.1039/b107327n

  日期：2002.3.25

  Reaction of (S)-3-acetoxyamino-2-[1-(t-butyldimethylsilyloxy)ethyl]quinazolin-4(3H)-one 5 (Q1NHOAc) with styrene and R(β)-substituted E-styrenes (R = SiMe3, Me, CH2Cl, CHCl2) gives the corresponding aziridines diastereoselectively. The diastereoselectivity increases in the same sense from 5 ∶ 1 → 20 ∶ 1 as the electron-withdrawing character of R increases [H(Me), CH2Cl, CHCl2] but is accompanied by a decrease in yield of aziridine. A similar increase in diastereoselectivity is found in the reaction of 3-acetoxyamino-2-(2,3,3-trimethylpropyl)quinazolin-4(3H)-one 38 (Q4NHOAc) with the same β-substituted styrenes.An explanation for these observations is offered based on a tighter, more symmetrical transition state for the aziridination of styrenes bearing the more electron-withdrawing β-substituents and is supported by SCF calculations.

  (S)-3-乙酰氧胺基-2-[1-(叔丁基二甲基硅氧基)乙基]喹唑啉-4(3H)-酮5 (Q1NHOAc)与苯乙烯及R(β)-取代的E-苯乙烯(R = SiMe3, Me, CH2Cl, CHCl2)的反应，可选择性地生成相应的氮丙啶。随着R的吸电子特性增强[H(Me), CH2Cl, CHCl2]，立体选择性从5:1增加到20:1，但氮丙啶的产率却降低。3-乙酰氧胺基-2-(2,3,3-三甲基丙基)喹唑啉-4(3H)-酮38 (Q4NHOAc)与相同的β-取代苯乙烯反应，也观察到类似的立体选择性增加。这些现象的解释基于更紧密、更对称的过渡态，用于带有更强吸电子β-取代基的苯乙烯的氮丙啶化，并通过SCF计算得到支持。
• 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%。
• Reactions of enol ethers and silyl ketene acetals with 3-acetoxyamino-2-ethylquinazolin-4(3H)-one: cleavage of N–N bonds in 3-alkylaminoquinazolin-4(3H)-ones
  作者：Robert S. Atkinson、Brian J. Kelly、John Williams

  DOI：10.1039/c39920000373

  日期：——

  Treatment of enol ethers and silyl ketene acetals with the N-acetoxyaminoquinazolone 1 gives α-aminoaaldehyde, α-aminoketone or α-aminoacid derivatives in good yields: cleavage of the N–N bond in 3-alkylaminoquinazolinone derivatives can be accomplished by samarium diiodide in tetrahydrofuran.

  对烯醚和硅基酮乙酸酯进行N-乙氧基氨基喹嗪酮1的处理，可良好产出α-氨基醛、α-氨基酮或α-氨基酸衍生物：在四氢呋喃中，采用碘化镨对3-烷基氨基喹嗪酮衍生物的N–N键进行断裂。
• Aziridination of alkenes using 3-acetoxyamino-2-trifluoromethylquinazolin-4(3H)-one
  作者：Robert S. Atkinson、Michael P. Coogan、Clive L. Cornell

  DOI：10.1039/p19960000157

  日期：——

  Oxidation of 3-amino-2-trifluoromethylquinazolin-4(3H)-one 6 with lead tetraacetate in dichloromethane gives the title 3-acetoxyamino derivative 7 which is isolable at room temperature and considerably more stable than the corresponding 2-alkyl substituted analogues. Compound 7 aziridinates alkenes in yields which are consistently higher than those from the 2-alkyl substituted analogues. Aziridinations

  用四乙酸铅在二氯甲烷中氧化3-氨基-2-三氟甲基喹唑啉-4（3H）-一6，得到标题3-乙酰氧基氨基衍生物7，其在室温下是可分离的，并且比相应的2-烷基取代的类似物更稳定。化合物7使叠氮基氮杂环丁烷烯的产率始终高于2-烷基取代的类似物的产率。已经研究了使用在喹唑啉酮环的2-位上带有其他吸电子基团的3-乙酰氧基氨基喹唑啉酮进行的叠氮化。