4-(3-bromophenyl)-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione

• 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-(3-bromophenyl)-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione
• 英文别名: 4-(3-bromophenyl)-7,7-dimethyl-3,4,6,8-tetrahydro-1H-quinazoline-2,5-dione
• 化学式: C₁₆H₁₇BrN₂O₂
• 分子量: 349.227
• InChiKey: ODCOBQKHISJPCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 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：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间溴苯甲醛 、 5,5-二甲基-1,3-环己二酮 、 尿素 在 zirconium(IV) oxychloride octahydrate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.42h， 以90%的产率得到4-(3-bromophenyl)-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione
  参考文献：
  名称：

  通过使用ZrOCl2.8H2O作为高效和可重复使用的催化剂，无溶剂合成新型和已知的八氢喹唑啉酮/硫酮

  摘要：

  尿素/硫脲，二甲酮与芳族醛之间的无溶剂反应在催化量的八氯化氧（IV）八水合氯化锆（ZrOCl 2 .8H 2 O）作为强力路易斯酸存在下，可以以高收率得到八氢喹唑啉酮/硫酮衍生物。该方法具有避免有机溶剂，生产无副产物的纯净产品，反应时间短和操作简单等优点。

  DOI：

  10.1002/jccs.201200145

文献信息

• Decorated Cu nanoparticles on ZPD as a novel and highly proficient nanocatalyst for synthesis of chromene and Biginelli reactions
  作者：Mehdi Najafi、Heshmatollah Alinezhad、Pouya Taheri、Elham Yeganeh-Salman、Shahram Ghasemi、Moein Ghorbanian

  DOI：10.1007/s11164-023-05220-2

  日期：2024.3

  ZPD is a type of metal–organic framework based on zinc ions. Its structure contains 2,5 pyridine dicarboxylic acid as ligand, and it was synthesized by the hydrothermal method. Its metal–organic framework has a high surface area, suitable micropores, and a very regular crystalline structure. In this study, Biginelli reaction and chromene synthesis were realized using Cu@ZPD as a catalyst. The prepared

  ZPD是一种基于锌离子的金属有机骨架。其结构以2,5吡啶二甲酸为配体，采用水热法合成。其金属有机骨架具有高表面积、合适的微孔和非常规则的晶体结构。本研究以Cu@ZPD为催化剂实现了Biginelli反应和色烯合成。所制备的产品具有高至优异的产率（80-96%）。通过傅里叶变换红外（FT-IR）、Brunauer-Emmett-Teller（BET）、热重分析（TGA）、X射线衍射（XRD）、场发射扫描电子显微镜（FE-SEM）对上述催化剂进行了鉴定。能量色散 X 射线 (EDX) 测绘、透射电子显微镜 (TEM) 和电感耦合等离子体发射光谱 (ICP-OES) 分析。通过使用 ICP-OES，检测到 Cu 负载量接近 3 wt%。制备的催化剂可重复使用6次而不会明显丧失催化活性。此外，还使用​​1 HNMR、13 CNMR 和 FT-IR 光谱来鉴定产物。
• Multicomponent Synthesis of 2,5-Dioxo- and 4-Aryl-5-oxo-2-thioxo-1,2,3,4,5,6,7,8-octahydroquinazolines
  作者：N. N. Tonkikh、A. Strakovs、M. V. Petrova

  DOI：10.1023/b:cohc.0000023766.76924.78

  日期：2004.1
• Indium(III) Trifluoromethanesulfonate: a Reusable Catalyst for the Sol-vent-free Synthesis of some Quinazolinones/thiones
  作者：Bahador Karami、Saeed Khodabakhshi、Sajad Karami

  DOI：10.5562/cca2087

  日期：——

  An environmentally friendly and clean procedure gives octahydroquinazolinones/thiones by a simple Biginelli condensation of urea/thiourea, aromatic aldehydes, and cyclic 1,3-diones in the presence of indium(III) trifluoromethanesulfonate (In(OTf)(3)) in solventless conditions. This method has advantages such as avoidance of the organic solvents, high yield of pure products without any by-product, short reaction times and operational simplicity.
• Synthesis and in vitro calcium antagonist activity of 4-aryl-7,7-dimethyl/1,7,7-trimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione derivatives
  作者：Mine Yarım、Selma Saraç、F.Sultan Kılıç、Kevser Erol

  DOI：10.1016/s0014-827x(02)00009-5

  日期：2003.1

  In this study, a series of 4-aryl-7,7-dimethyl and 1,7,7-trimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-diones (1-25) were synthesized by condensing urea or N-methylurea with 5,5-dimethyl-1,3-cyclohexanedione and appropriate aromatic aldehydes according to the Biginelli reaction. The structures of the compounds were confirmed by spectral data and elementary analysis. The calcium antagonist activity of the compounds was tested in vitro on isolated rat ileum and lamb carotid artery. Compounds 16 and 19 were the most active derivatives on isolated rat ileum compared with the standard nicardipine. On isolated aortic strips of lamb the calcium antagonist activity of compound 16 (maximum relaxant effect: 38.83+/-5.84%) was found as high as that of nicardipine (maximum relaxant effect: 35.50+/-4.16%) used as a reference drug.