4-phenyl-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thione-5-one

• 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: 4-phenyl-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thione-5-one
• 英文别名: 4-phenyl-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thione；7,7-dimethyl-4-phenyl-2-thioxo-2,3,4,6,7,8-hexahydro-1H-quinazolin-5-one；7,7-dimethyl-4-phenyl-2-thioxo-2,3,4,6,7,8-hexahydro-5(1H)-quinazolinone；4-phenyl-7,7-dimethyl-3,4,6,8-tetrahydro-quinazolin-5-one-2-thione；octahydroquinazoline-2-thione；Quinazolin-5(6H)-one, 1,2,3,4,7,8-hexahydro-7,7-dimethyl-4-phenyl-2-thioxo-；7,7-dimethyl-4-phenyl-2-sulfanylidene-3,4,6,8-tetrahydro-1H-quinazolin-5-one
• 化学式: C₁₆H₁₈N₂OS
• 分子量: 286.398
• InChiKey: LQOWAPAUEFCXJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenyl-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thione-5-one 在 sodium azide 、 mercury(II) diacetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以76%的产率得到9-phenyl-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one
  参考文献：
  名称：

  One-Step Synthesis of Tetrazolo[1,5-a]pyrimidines by Cyclization Reaction of Dihydropyrimidine-2-thiones with Sodium Azide

  摘要：

  An novel, versatile and cost-effective approach for tetrazolo[1,5-a]pyrimidines and tetrazolo[1,5-a]quinazolines from cyclization reaction of dihydropyrimidinethiones with sodium azide in the presence of mercuric acetate is described. To compare this procedure with the conventional method, we carried out the cyclization reactions through direct functionalization of the pyrimidinethione core, which obtained from Biginelli 3,4-dihydropyrimidine-2-thiones or 4-aryl-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thiones.

  DOI：

  10.3987/com-11-12351
• 作为产物：
  描述：

  苯甲醛 、 5,5-二甲基-1,3-环己二酮 、 硫脲 在 potassium phtalimide 作用下， 反应 3.0h， 以88%的产率得到4-phenyl-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thione-5-one
  参考文献：
  名称：

  Solvent-free efficient one-pot synthesis of Biginelli and Hantzsch compounds catalyzed by potassium phthalimide as a green and reusable organocatalyst

  摘要：

  本文报道了在无溶剂条件下，于120°C下使用邻苯二甲酰亚胺钾（PPI）进行Hantzsch 1,4-二氢吡啶、多氢喹啉、3,4-二氢嘧啶-2(1H)-酮/硫酮以及八氢喹唑啉酮的一步多组分简单绿色合成。该方法操作简便，环境友好，且产率相对较高。此外，该方法还具有高效、清洁、绿色以及催化剂可重复使用的优点。

  DOI：

  10.1007/s11164-014-1621-x

文献信息

• S- and C-nucleosidoquinazoline as new nucleoside analogs with potential analgesic and anti-inflammatory activity
  作者：Abdel-Rahman B.A. El-Gazzar、Hend N. Hafez、Hebat-Allah S. Abbas

  DOI：10.1016/j.ejmech.2009.05.025

  日期：2009.10

  Thioglycosides and C-glycosides have received considerable attention, because they are widely employed as biological inhibitors, inducers and ligands for affinity chromatography of carbohydrate-processing enzymes and proteins. Moreover, they are promising candidates in synthetic carbohydrate chemistry as convenient and versatile glycosyl donors. Among these glycosyl donors are the thioglycosyl and

  硫代糖苷和C-糖苷已被广泛关注，因为它们被广泛用作生物抑制剂，诱导剂和配体，用于碳水化合物加工酶和蛋白质的亲和层析。而且，它们在合成碳水化合物化学中有望成为方便且用途广泛的糖基供体。这些糖基供体中的硫代糖基和N-糖基杂环在各种反应条件下足够稳定，并具有易于转化为多种其他功能的能力。我们在这里报告了2-硫代-喹唑啉1a – c的合成，这些合成被用作合成S型核苷的基础10，11和无环Ç类型的核苷类似物14和它们的止痛和抗炎活性进行评价得到良好的结果。
• Efficient, One-Pot Synthesis of Polyfunctionalised Octahydroquinazolin-2,5-Diones Catalysed by Fe₃O₄ Nanoparticles
  作者：Vahid Reza Hedayati、Mohammad Ali Ghasemzadeh

  DOI：10.3184/174751915x14199511243271

  日期：2015.1

  Using an efficient and eco-friendly approach, 14 4-aryl-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazolin-2,5-diones (and six of their 2-thione analogues) were prepared in good yields and in short reaction times by a three-component reaction of an araldehyde, dimedone and urea (or thiourea) using Fe₃O₄ nanoparticles in aqueous ethanol under reflux conditions. The Fe₃O₄ nanoparticles, which were easily prepared and could be recycled, were fully characterised by TEM, SEM, XRD, EDX, VSM and FTIR analysis.

  在回流条件下，在乙醇水溶液中使用 Fe3O4 纳米粒子，通过芳醛、二酮和脲（或硫脲）的三组分反应，采用高效、环保的方法制备了 14 个 4-芳基-7,7-二甲基-1,2,3,4,5,6,7,8-八氢喹唑啉-2,5-二酮（及其 6 个 2-硫酮类似物），产率高、反应时间短。通过 TEM、SEM、XRD、EDX、VSM 和 FTIR 分析，对易于制备且可回收利用的 Fe3O4 纳米粒子进行了全面表征。
• Solvent-free efficient one-pot synthesis of Biginelli and Hantzsch compounds catalyzed by potassium phthalimide as a green and reusable organocatalyst
  作者：Hamzeh Kiyani、Maryam Ghiasi

  DOI：10.1007/s11164-014-1621-x

  日期：2015.8

  The usage of potassium phthalimide (PPI) for the simple and green one-step multicomponent synthesis of Hantzsch 1,4-dihydropyridines, polyhydroquinolines, 3,4-dihydropyrimidin-2(1H)-ones/thiones, and octahydroquinazolinones under solventless conditions at 120 °C is reported. The method is operationally simple, environmentally benign, and has relatively high yields. The other merits of this method include efficient, clean, green, and catalyst reusability.

  本文报道了在无溶剂条件下，于120°C下使用邻苯二甲酰亚胺钾（PPI）进行Hantzsch 1,4-二氢吡啶、多氢喹啉、3,4-二氢嘧啶-2(1H)-酮/硫酮以及八氢喹唑啉酮的一步多组分简单绿色合成。该方法操作简便，环境友好，且产率相对较高。此外，该方法还具有高效、清洁、绿色以及催化剂可重复使用的优点。
• Synthesis of novel thiazolo[2,3-<i>b</i>]quinazolines by cyclization reaction of octahydroquinazoline-2-thiones with <i>α-</i>bromoketones
  作者：Zheng-Jun Quan、Ying Wei、Xi-Cun Wang

  DOI：10.1515/hc.2011.041

  日期：2011.12.1

  Abstract Novel thiazolo[2,3-b]quinazolines were prepared by the cyclization reaction between octahydroquinazoline-2-thiones with α-bromoketones, which provides a readily accessible multifunctionalized quinazoline template for diversity-oriented synthesis.

  摘要 通过八氢喹唑啉-2-硫酮与α-溴酮之间的环化反应制备了新型噻唑并[2,3-b]喹唑啉，为面向多样性的合成提供了一种易于获得的多功能喹唑啉模板。
• Microwave induced new route to acridine and quinazoline derivatives using TLC plates
  作者：M. Kidwai、S. Saxena、R. Mohan

  DOI：10.1002/jhet.5570420435

  日期：2005.5

  Microwave (MW) assisted synthesis of acridine and quinazoline derivatives was performed on thin layer chromatography (TLC) plates. This versatile, simple and economical green methodology is readily amenable to parallel synthesis of acridine and quinazoline compound libraries.

  微波（MW）辅助合成的cr啶和喹唑啉衍生物在薄层色谱（TLC）板上进行。这种通用，简单且经济的绿色方法很容易适用于cr啶和喹唑啉化合物库的并行合成。