3-methyl-2-vinyl-3H-quinazolin-4-one | 306996-59-8

• 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: 3-methyl-2-vinyl-3H-quinazolin-4-one
• 英文别名: 3-methyl-2-vinylquinazolin-4(3H)-one；2-Ethenyl-3-methylquinazolin-4-one
• CAS: 306996-59-8
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: ZONNKXWQTMXETG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-2-vinyl-3H-quinazolin-4-one 在 sodium azide 作用下， 以 四氢呋喃 、 水 为溶剂， 以50%的产率得到3-methyl-2-(2-azidoethyl)-3H-quinazolin-4-one
  参考文献：
  名称：

  Synthesis and Reactions of some 2-Vinyl-3H-quinazolin-4-ones

  摘要：

  A simple, high-yielding synthesis of 2-vinyl-3H-quinazolin-4-one, 2-(1-chlorovinyl)-3H-quinazolin-4-one and 2-(1-bromovinyl)-3H-quinazolin-4-one. The 2-vinylquinazolinones 11a and 14 participate readily in nucleophilic addition reactions. Treatment with both carbon and nitrogen nucleophiles results in a clean conversion into a variety of 2-substituted 3H-quinazolin-4-one derivatives. The 2-(1-halovinyl)-3H-quinazolin-4-ones 11b and Ile reacted with carbon nucleophiles to give several derivatives of 2-substituted 3H-quinazolin-4-one, such as dihydrofurancarboxylic ethyl ester 23. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00595-0
• 作为产物：
  描述：

  2-(3-氯丙酰胺)苯甲酰胺 在 sodium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 5.25h， 生成 3-methyl-2-vinyl-3H-quinazolin-4-one
  参考文献：
  名称：

  喹唑啉酮的新型异恶唑烷偶联物——合成、抗病毒和细胞抑制活性

  摘要：

  通过 N-甲基-C-（二乙氧基磷酰基）硝酮与 N3-取代的 2-乙烯基-3H-喹唑啉的 1,3-偶极环加成反应，合成了一系列在 C5 处被各种喹唑啉酮取代的新型（3-二乙氧基磷酰基）异恶唑烷。 4个。评估了所有异恶唑烷对多种 DNA 和 RNA 病毒的抗病毒活性。异恶唑烷 trans-11f/cis-11f (90:10)、trans-11h 和 trans-11i/cis-11i (97:3) 对 VZV（TK+ 菌株）表现出弱活性（EC50 = 6.84、15.29 和 9.44 μM）仅比用作参考药物的阿昔洛韦低一个数量级。膦酸盐 trans-11b/cis-11b (90:10)、trans-11c、trans-11e/cis-11e (90:10) 和 trans-11g 似乎对巨细胞病毒有轻微活性 (EC50 = 27–45 μM)。

  DOI：

  10.3390/molecules21070959

文献信息

• [EN] HETEROARYL COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS HÉTÉROARYLÉS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SUNOVION PHARMACEUTICALS INC

  公开号：WO2011150156A2

  公开（公告）日：2011-12-01

  Provided herein are heteroaryl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. In one embodiment, the compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as CNS disorders and metabolic disorders, including, but not limited to, e.g., neurological disorders, psychosis, schizophrenia, obesity, and diabetes.
• New Isoxazolidine-Conjugates of Quinazolinones—Synthesis, Antiviral and Cytostatic Activity
  作者：Dorota Piotrowska、Graciela Andrei、Dominique Schols、Robert Snoeck、Magdalena Grabkowska-Drużyc

  DOI：10.3390/molecules21070959

  日期：——

  quinazolinones have been synthesized by the 1,3-dipolar cycloaddition of N-methyl-C-(diethoxyphosphoryl)nitrone with N3-substitued 2-vinyl-3H-quinazolin-4-ones. All isoxazolidines were assessed for antiviral activity against a broad range of DNA and RNA viruses. Isoxazolidines trans-11f/cis-11f (90:10), trans-11h and trans-11i/cis-11i (97:3) showed weak activity (EC50 = 6.84, 15.29 and 9.44 μM) toward

  通过 N-甲基-C-（二乙氧基磷酰基）硝酮与 N3-取代的 2-乙烯基-3H-喹唑啉的 1,3-偶极环加成反应，合成了一系列在 C5 处被各种喹唑啉酮取代的新型（3-二乙氧基磷酰基）异恶唑烷。 4个。评估了所有异恶唑烷对多种 DNA 和 RNA 病毒的抗病毒活性。异恶唑烷 trans-11f/cis-11f (90:10)、trans-11h 和 trans-11i/cis-11i (97:3) 对 VZV（TK+ 菌株）表现出弱活性（EC50 = 6.84、15.29 和 9.44 μM）仅比用作参考药物的阿昔洛韦低一个数量级。膦酸盐 trans-11b/cis-11b (90:10)、trans-11c、trans-11e/cis-11e (90:10) 和 trans-11g 似乎对巨细胞病毒有轻微活性 (EC50 = 27–45 μM)。
• Synthesis and Reactions of some 2-Vinyl-3H-quinazolin-4-ones
  作者：Anette Witt、Jan Bergman

  DOI：10.1016/s0040-4020(00)00595-0

  日期：2000.9

  A simple, high-yielding synthesis of 2-vinyl-3H-quinazolin-4-one, 2-(1-chlorovinyl)-3H-quinazolin-4-one and 2-(1-bromovinyl)-3H-quinazolin-4-one. The 2-vinylquinazolinones 11a and 14 participate readily in nucleophilic addition reactions. Treatment with both carbon and nitrogen nucleophiles results in a clean conversion into a variety of 2-substituted 3H-quinazolin-4-one derivatives. The 2-(1-halovinyl)-3H-quinazolin-4-ones 11b and Ile reacted with carbon nucleophiles to give several derivatives of 2-substituted 3H-quinazolin-4-one, such as dihydrofurancarboxylic ethyl ester 23. (C) 2000 Elsevier Science Ltd. All rights reserved.