7'-chloro-spiro[cyclohexane-1,2'(1'H)-quinazolin]-4'(3'H)-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: 7'-chloro-spiro[cyclohexane-1,2'(1'H)-quinazolin]-4'(3'H)-one
• 英文别名: 7'-chloro-1'H-spiro[cyclohexane-1,2'-quinazolin]-4'(3'H)-one；7-chloro-2,2-pentamethylene-1,2-dihydroquinazolin-4(3H)-one；7-Chlorospiro[1,3-dihydroquinazoline-2,1'-cyclohexane]-4-one
• 化学式: C₁₃H₁₅ClN₂O
• 分子量: 250.728
• InChiKey: MFJIGEFRENMNDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基-4-氯苯腈 、 环己酮 在 potassium tert-butylate 作用下， 反应 0.2h， 以91%的产率得到7'-chloro-spiro[cyclohexane-1,2'(1'H)-quinazolin]-4'(3'H)-one
  参考文献：
  名称：

  芳香族邻氨基腈与羰基化合物的发散转化

  摘要：

  发现了芳族邻氨基腈与羰基化合物的环缩合反应的改进的Friedländer转化。系统研究表明，在存在ZnCl 2的情况下，新的转化和经典的Friedländer圆环构成了一对发散反应，并且在碱的存在下实现了该发散反应的受控PDF转化。

  DOI：

  10.1002/jhet.804

文献信息

• Gemini basic ionic liquid as bi-functional catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones at room temperature
  作者：Apurba Dutta、Krishnaiah Damarla、Arvind Kumar、Prakash J. Saikia、Diganta Sarma

  DOI：10.1016/j.tetlet.2019.151587

  日期：2020.3

  A cascade synthesis of 2,3-dihydroquinazolin-4(1H)-ones has been developed from 2-aminobenzonitriles and carbonyl analogues using Gemini basic ionic liquid as green catalyst cum solvent at room temperature. Both aldehydes and ketones were condensed with 2-aminobenzonitriles affording good to excellent yields of products. Moreover, the ionic liquids can be reused up to 5th cycle without significant

  在室温下，使用Gemini碱性离子液体作为绿色催化剂和溶剂，由2-氨基苯甲腈和羰基类似物开发了2,3-二氢喹唑啉-4（1 H）-ones的级联合成。醛和酮都与2-氨基苄腈缩合，从而提供了良好或优异的产物收率。此外，离子液体可重复使用至第5个循环，而不会显着降低催化活性。
• An efficient synthesis of quinazoline derivatives with the aid of low-valent titanium reagent
  作者：Daqing Shi、Chunling Shi、Juxian Wang、Liangce Rong、Qiya Zhuang、Xiangshan Wang

  DOI：10.1002/jhet.5570420201

  日期：2005.3

  Quinazolin-4(3H)-ones, 1,2-dihydroquinazolin-4(3H)-ones, 3,4-dihydroquinazolines, imidazo[1,2-c]-quinazolines and 5,6-dihydroimidazo[1,2-c]quinazolines were synthesized by the novel reductive reaction of nitro group, N-H bond and ortho-ester, aldehydes or ketones promoted by the low-valent titanium reagent (TiCl4-Zn system). The structures of these compounds were characterized by elemental analysis

  喹唑啉-4（3 H）-one，1,2-二氢喹唑啉-4（3 H）-one，3,4-二氢喹唑啉，咪唑并[1,2- c ]-喹唑啉和5,6-二氢咪唑并[1,2 - c ^ ]喹唑啉通过将低价钛试剂（促进的TiCl硝基，NH键和原酸酯，醛或酮的新型还原反应，合成4 -Zn系统）。这些化合物的结构通过元素分析，IR和1 HNMR光谱进行表征，并通过单晶X射线衍射分析进一步证实。
• Synthesis of quinolines via Friedländer reaction catalyzed by CuBTC metal–organic-framework
  作者：Elena Pérez-Mayoral、Zuzana Musilová、Barbara Gil、Bartosz Marszalek、Miroslav Položij、Petr Nachtigall、Jiri Čejka

  DOI：10.1039/c2dt11978a

  日期：——

  Friedländer condensation between 2-aminoaryl ketones and different carbonyl compounds, catalyzed by CuBTC was investigated by a combination of various experimental techniques and by density functional theory based modelling. CuBTC exhibiting hard Lewis acid character showed highly improved catalytic activity when compared with other molecular sieves showing high concentraion of Lewis acid sites, e.g. in BEA and (Al)SBA-15. Polysubstituted quinolines were synthesized via a Friedländer reaction catalyzed by CuBTC under the solvent-free conditions. High concentration of active sites in CuBTC together with the concerted effect of a pair of adjacent Cu2+ coordinatively unsaturated active sites are behind a very high quinoline yield reached within a short reaction time. Results reported here make CuBTC a promising catalyst for other Lewis acid-promoted condensations, including those leading to biologically active compounds with a particular relevance for the pharmaceutical industry. The mechanism of a catalyzed Friedländer reaction investigated computationally is also reported.

  对Friedländer缩聚反应在2-氨基芳基酮和不同羰基化合物之间，采用CuBTC作为催化剂的研究，结合了多种实验技术和基于密度泛函理论的建模。具有硬路易斯酸特性的CuBTC展现出了比其他分子筛（如BEA和(Al)SBA-15，它们的路易斯酸位点浓度高）更高的催化活性。在无溶剂条件下，通过CuBTC催化的Friedländer反应合成了多取代喹啉。CuBTC中高浓度的活性位点以及相邻的一对配位不饱和的Cu2+活性位点的协同效应，是其在一小段时间内达到极高喹啉产率的原因。这里报告的结果使CuBTC成为其他路易斯酸促进缩聚反应的有力催化剂，包括那些导致生物活性化合物产生的反应，对制药行业具有特别重要意义。同时，还报告了通过计算研究得出的催化Friedländer反应的机理。
• Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media with β-cyclodextrin-SO₃H as a recyclable catalyst
  作者：Jian Wu、Xianli Du、Juan Ma、Yuping Zhang、Qingcai Shi、Lijun Luo、Baoan Song、Song Yang、Deyu Hu

  DOI：10.1039/c3gc42400f

  日期：——

  A β-cyclodextrin-SO₃H-assisted, convenient and efficient strategy for the preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media is presented.

  一种在水介质中利用β-环糊精-SO3H辅助的便捷高效策略，用于制备2,3-二氢喹唑啉-4(1H)-酮衍生物。
• Synthesis of quinazolin-4(3 H )-ones and 1,2-dihydroquinazolin-4(3 H )-ones with the aid of a low-valent titanium reagent
  作者：Daqing Shi、Liangce Rong、Juxian Wang、Qiya Zhuang、Xiangshan Wang、Hongwen Hu

  DOI：10.1016/s0040-4039(03)00449-0

  日期：2003.4

  A short and facile synthesis of a series of quinazolin-4(3H)-ones and 1,2-dihydroquinazolin-4(3H)-ones was accomplished in good yields via the novel reductive cyclization of o-nitrobenzamides and triethyl orthoformate, aldehydes or ketones promoted by TiCl4/Zn.

  一系列喹唑啉-4-的短而简便合成（3 ħ） -酮和1,2-二氢喹唑啉-4（3 H ^） -酮在良好的产率通过的新颖还原性环化完成ö -nitrobenzamides和原甲酸三乙酯， TiCl 4 / Zn促进的醛或酮。