1-methyl-3-(2'-phenylethyl)-1H,3H-quinazoline-2,4-dione | 75652-62-9

• 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: 1-methyl-3-(2'-phenylethyl)-1H,3H-quinazoline-2,4-dione
• 英文别名: 1-methyl-3-phenethyl-1H,3H-quinazoline-2,4-dione；1-methyl-3-phenethylquinazoline-2,4(1H,3H)-dione；1-Methyl-3-(2-phenylethyl)-2,4(1H,3H)-quinazolinedione；1-methyl-3-(2-phenylethyl)quinazoline-2,4-dione
• CAS: 75652-62-9
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: VJWBYNSMAFYKPV-UHFFFAOYSA-N

物化性质

• 熔点：
  99-101 °C
• 沸点：
  448.6±38.0 °C(Predicted)
• 密度：
  1.220±0.06 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：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻溴苯甲酸甲酯 在 tris(dibenzylideneacetone)dipalladium (0) 、 sodium hydride 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1-methyl-3-(2'-phenylethyl)-1H,3H-quinazoline-2,4-dione
  参考文献：
  名称：

  串联钯催化的尿素芳基化-分子内酯酰胺化：3-烷基化的2,4-喹唑啉二酮的区域选择性合成。

  摘要：

  邻卤代苯甲酸酯可与单烷基脲按串联钯催化的芳基化酯酰胺化顺序结合，以生成喹唑啉二酮产物。反应对于形成3-N-烷基异构体是区域选择性的。两个偶联配偶体的显着变化是可能的，从而允许合成各种取代的喹唑啉二酮，例如制备简单的不对称二烷基化天然产物。[反应：看文字]

  DOI：

  10.1021/ol062009x

文献信息

• Facile One-Pot Synthesis of Quinazoline-2,4-dione Derivatives and Application to Naturally Occurring Alkaloids from Zanthoxylum Arborescens
  作者：Xin Li、Yong-Rok Lee

  DOI：10.5012/bkcs.2011.32.6.2121

  日期：2011.6.20

  method that canefficiently provide quinazoline-2,4-dione derivatives. Wereport herein a convenient one-pot synthesis of quinazoline-2,4-dione derivatives. We also report on the synthesis of thenaturally occurring alkaloids 2 and 3. Results and DiscussionA two-step reaction for the synthesis of quinazoline-2,4-dione derivatives starting from isatoic anhydride and amineshas already been described.

  仍然需要一种更方便、更高效的合成方法，可以有效地提供喹唑啉-2,4-二酮衍生物。本文报道了一种方便的一锅法合成喹唑啉-2,4-二酮衍生物。我们还报告了天然存在的生物碱 2 和 3 的合成。结果和讨论已经描述了从靛红酸酐和胺开始合成喹唑啉-2,4-二酮衍生物的两步反应。
• Syntheses of Quinazoline-2,4-dione Alkaloids and Analogues from Mexican Zanthoxylum Species †
  作者：I. Rivero、K. Espinoza、R. Somanathan

  DOI：10.3390/90700609

  日期：——

  Quinazolinone and quinazolinedione derivatives are of considerable interest due to their wide array of pharmacological properties. In this paper we report the synthesis of ten quinazolinediones. The previous isolation of two of these compounds, namely 1-methyl-3-(2'-phenylethyl)-1H,3H-quinazoline-2,4-dione and 1-methyl-3-[2'-(4'- methoxyphenyl)ethyl]-lH,3H-quinazoline-2,4-dione, from the seed husks of Mexican Zanthoxylum species has been reported

  喹唑啉酮和喹唑啉二酮衍生物因其广泛的药理性质而受到广泛关注。在本文中，我们报告了十种喹唑啉二酮的合成。此前已经报道了其中两个化合物，即1-甲基-3-(2'-苯乙基)-1H,3H-喹唑啉-2,4-二酮和1-甲基-3-[2'-(4'-甲氧基苯基)乙基]-1H,3H-喹唑啉-2,4-二酮，来自墨西哥刺柠檬种子的种皮。
• Alkaloids of some Mexican Zanthoxylum species
  作者：David L. Dreyer、R.C. Brenner

  DOI：10.1016/0031-9422(80)85141-7

  日期：——

  Abstract Two new 4-quinazolone alkaloids have been isolated from seed husks of Zanthoxylum arborescens . Based on their spectroscopic properties they have been assigned structures, 1-methyl-3-(2′-phenylethyl)-1H,3H-quinazoline-2,4-dione and 1-methyl-3-[2′-(4″-methoxyphenyl)ethyl]-1H,3H-quinazoline-2,4-dione. These structural assignments have been confirmed by synthesis. Skimmianine has been obtained

  摘要 从花椒籽壳中分离得到两种新的4-喹唑酮类生物碱。根据它们的光谱特性，它们被指定为结构 1-methyl-3-(2'-phenylethyl)-1H,3H-quinazoline-2,4-dione 和 1-methyl-3-[2'-(4″-甲氧基苯基)乙基]-1H,3H-喹唑啉-2,4-二酮。这些结构分配已通过合成得到证实。Skimmianine 已从 Z. dimoncillo 和 Z. caribaeum 的叶提取物中获得，而skimmianine 和 scopeletin 已从 Z. fagara 的叶提取物中分离出来。
• Nickel-Catalyzed Synthesis of Quinazolinediones
  作者：Gregory L. Beutner、Yi Hsiao、Thomas Razler、Eric M. Simmons、William Wertjes

  DOI：10.1021/acs.orglett.7b00052

  日期：2017.3.3

  A nickel(0)-catalyzed method for the synthesis of quinazolinediones from isatoic anhydrides and isocyanates is described. High-throughput ligand screening revealed that XANTPHOS was the optimal ligand for this transformation. Subsequent optimization studies, supported by kinetic analysis, significantly expanded the reaction scope. The reaction exhibits a case of substrate inhibition kinetics with respect to the isocyanate. Preliminary results on an asymmetric synthesis of atropisomeric quinazolinediones are reported.
• Tandem Palladium-Catalyzed Urea Arylation−Intramolecular Ester Amidation:  Regioselective Synthesis of 3-Alkylated 2,4-Quinazolinediones
  作者：Michael C. Willis、Robert H. Snell、Anthony J. Fletcher、Robert L. Woodward

  DOI：10.1021/ol062009x

  日期：2006.10.1

  o-Halo benzoates can be combined with monoalkyl ureas in a tandem palladium-catalyzed arylation-ester amidation sequence to deliver quinazolinedione products. The reactions are regioselective for formation of the 3-N-alkyl isomers. Significant variation of both coupling partners is possible, allowing the synthesis of a diverse array of substituted quinazolinediones, exemplified by the preparation of

  邻卤代苯甲酸酯可与单烷基脲按串联钯催化的芳基化酯酰胺化顺序结合，以生成喹唑啉二酮产物。反应对于形成3-N-烷基异构体是区域选择性的。两个偶联配偶体的显着变化是可能的，从而允许合成各种取代的喹唑啉二酮，例如制备简单的不对称二烷基化天然产物。[反应：看文字]

表征谱图