2,2-dimethyl-3-(1-methylethylidene)amino-4-oxo-1,2,3,4-tetrahydroquinazoline | 19558-22-6

• 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: 2,2-dimethyl-3-(1-methylethylidene)amino-4-oxo-1,2,3,4-tetrahydroquinazoline
• 英文别名: 3-(propan-2-ylideneamino)-2,3-dihydro-2,2-dimethylquinazolin-4(1H)-one；3-(isopropylideneamino)-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one；3-isopropylideneamino-2,2-dimethyl-2,3-dihydro-1H-quinazolin-4-one；2,2-dimethyl-3-(propan-2-ylideneamino)-1H-quinazolin-4-one
• CAS: 19558-22-6
• 化学式: C₁₃H₁₇N₃O
• 分子量: 231.297
• InChiKey: IYFQTKRPLULTFL-UHFFFAOYSA-N

物化性质

• 溶解度：
  34.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙酮 、 2,6-diacetylpyridine 2-aminobenzoylhydrazone 在 dibutyltin chloride 作用下， 生成 2,2-dimethyl-3-(1-methylethylidene)amino-4-oxo-1,2,3,4-tetrahydroquinazoline
  参考文献：
  名称：

  Pelizzi, Corrado; Pelizzi, Giancarlo; Predieri, Giovanni, Gazzetta Chimica Italiana, 1982, vol. 112, # 7/8, p. 343 - 344

  摘要：

  DOI：

文献信息

• Combinatorial Synthesis of 3-Arylideneaminoquinazolin-4(1<i>H</i>)-one Derivatives Catalyzed by Iodine in Ionic Liquids
  作者：Xiang-Shan Wang、Jie Sheng、Lian Lu、Ke Yang、Yu-Ling Li

  DOI：10.1021/co1000713

  日期：2011.3.14

  A combinatorial synthesis of 3-arylideneaminoquinazolin-4(1H)-one derivatives is described by a reaction of 2-aminobenzohydrazides with two equivalents of aldehydes or ketones in ionic liquids catalyzed by iodine. Controlling the reaction temperature or reducing the activity of the substrates, respectively, the intermediate products of hydrazones were obtained first, and then they were applied to react

  通过2-氨基苯甲酰肼与二当量的醛或酮在碘催化的离子液体中的反应，描述了3-芳基氨基喹唑啉-4（1H）-一衍生物的组合合成。分别控制反应温度或降低底物的活性，首先获得的中间产物，然后将它们与各种芳族醛反应而不分离，从而导致喹唑啉酮衍生物的结构多样化。
• Diverse Confirmations in the Crystal Structures of 2,3-Dihydro-2,2-dimethylquinazolin-4(1H)-one Derivatives
  作者：Jie Sheng、Mei-Mei Zhang、Lian Lu、Xiang-Shan Wang

  DOI：10.1007/s10870-012-0303-z

  日期：2012.7

  The 3-(propan-2-ylideneamino)-2,3-dihydro-2,2-dimethylquinazolin-4(1H)-one and 3-(3-nitrobenzylideneamino)-2,3-dihydro-2,2-dimethylquinazolin-4(1H)-one were synthesized and characterized by IR, 1H NMR and HRMS. The molecular structures were further confirmed by X-ray diffraction analysis. The former 1, C13H17N3O, is monoclinic, space group P2(1)/c, a = 9.056(2), b = 9.439(2), c = 14.872(3) Å, β = 133.121(12)°, Z = 4, V = 1270.9(5) Å3. The latter 2, C17H16N4O3, is also monoclinic, space group P2(1)/c, a = 10.0006(2), b = 12.2298(3), c = 13.3255(3) Å, β = 96.602(2)°, Z = 4, V = 1618.97(6) Å3. It is very interesting that the pyrimidine ring in the 1 adopts a half-chair confirmation, while adapting a skew-boat one in the structure of 2. The 3-(propan-2-ylideneamino)-2,3-dihydro-2,2-dimethylquinazolin-4(1H)-one and 3-(3-nitrobenzylideneamino)-2,3-dihydro-2,2-dimethylquinazolin-4(1H)-one were synthesized and characterized by IR, 1H NMR and HRMS. The molecular structures were further confirmed by X-ray diffraction analysis. The former 1, C13H17N3O, is monoclinic, space group P2(1)/c, a = 9.056(2), b = 9.439(2), c = 14.872 (3) Å, β = 133.121(12)°, Z = 4, V = 1270.9 (5) Å3. The latter 2, C17H16N4O3, is also monoclinic, space group P2(1)/c, a = 10.0006(2), b = 12.2298(3), c = 13.3255(3) Å, β = 96.602(2)°, Z = 4, V = 1618.97(6) Å3. It is very interesting that the pyrimidine ring in the 1 adopts a half-chair confirmation, while adapting a skew-boat one in the structure of 2.

  合成了 3-(丙-2-亚基氨基)-2,3-二氢-2,2-二甲基喹唑啉-4(1H)-酮和 3-(3-硝基亚苄基氨基)-2,3-二氢-2,2-二甲基喹唑啉-4(1H)-酮，并通过红外光谱、1H NMR 和 HRMS 进行了表征。分子结构通过 X 射线衍射分析得到进一步证实。前者 1（C13H17N3O）为单斜晶系，空间群为 P2(1)/c，a = 9.056(2), b = 9.439(2), c = 14.872(3) Å, β = 133.121(12)°, Z = 4, V = 1270.9(5) Å3。后一种 2，C17H16N4O3，也是单斜晶体，空间群 P2(1)/c，a = 10.0006(2)，b = 12.2298(3), c = 13.3255(3) Å, β = 96.602(2)°, Z = 4, V = 1618.97(6) Å3.非常有趣的是，1 中的嘧啶环采用了半椅确认，而在 2 的结构中则采用了斜船确认。合成了 3-(丙-2-亚氨基)-2,3-二氢-2,2-二甲基喹唑啉-4(1H)-酮和 3-(3-硝基亚苄基氨基)-2,3-二氢-2,2-二甲基喹唑啉-4(1H)-酮，并通过红外光谱、1H NMR 和 HRMS 对其进行了表征。分子结构通过 X 射线衍射分析得到进一步证实。前者 1（C13H17N3O）为单斜晶系，空间群为 P2(1)/c，a = 9.056(2), b = 9.439(2), c = 14.872 (3) Å, β = 133.121(12)°, Z = 4, V = 1270.9 (5) Å3.后一种 2，C17H16N4O3，也是单斜晶体，空间群 P2(1)/c，a = 10.0006(2)，b = 12.2298(3), c = 13.3255(3) Å, β = 96.602(2)°, Z = 4, V = 1618.97(6) Å3.非常有趣的是，1 中的嘧啶环采用半椅确认，而 2 的结构则采用斜舟确认。
• Identification of novel quinazolin-4(3H)-ones as inhibitors of thermolysin, the prototype of the M4 family of proteinases
  作者：Mahmud Tareq Hassan Khan、Rasool Khan、Yimingjiang Wuxiuer、Mohammad Arfan、Manzoor Ahmed、Ingebrigt Sylte

  DOI：10.1016/j.bmc.2010.04.083

  日期：2010.6.15

  A combinatorial series of novel quinazolin-4(3H)-ones were synthesised and their structures were established based on spectroscopic data (IR, NMR, EI-MS, and FAB-MS). The compounds were tested for inhibition of the zinc metalloproteinase thermolysin (TLN) utilizing a chemical array-based approach. Some of the compounds were found to inhibit TLN, with IC50 values ranging from 0.0115 mu M (compound 3) to 122,637 mu M (compound 29). Compound 3 [3-phenyl-2-(trifluoromethyl) quinazolin-4(3H)-one] (IC50 = 0.0115 mu M) and compound 35 [3-(isopropylideneamino)-2,2-dimethyl-2,3-dihydroquinazolin-4 (1H)-one] (IC50 = 0.2477 mu M) were found to be the most potent inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.
• Pelizzi, Corrado; Pelizzi, Giancarlo; Predieri, Giovanni, Gazzetta Chimica Italiana, 1982, vol. 112, # 7/8, p. 343 - 344
  作者：Pelizzi, Corrado、Pelizzi, Giancarlo、Predieri, Giovanni

  DOI：——

  日期：——