2,3-dihydro-1-methylpyrrolo<2,1-b>quinazolin-9(1H)-one | 97475-24-6

• 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: 2,3-dihydro-1-methylpyrrolo<2,1-b>quinazolin-9(1H)-one
• 英文别名: 1-Methyl-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
• CAS: 97475-24-6
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: DCRZVWIQIPZWER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-乙氧基-2-氧代乙酸 、 2,3-dihydro-1-methylpyrrolo<2,1-b>quinazolin-9(1H)-one 在 sodium ethanolate 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 12.0h， 以79.4%的产率得到ethyl (2Z)-2-hydroxy-2-(1-methyl-9-oxo-1,2-dihydropyrrolo[2,1-b]quinazolin-3-ylidene)acetate
  参考文献：
  名称：

  Horvath, Karoly; Koekoesi, Jozsef; Hermecz, Istvan, Journal of the Chemical Society. Perkin transactions II, 1989, p. 1613 - 1616

  摘要：

  DOI：
• 作为产物：
  描述：

  5-Methyl-1-(2-nitrobenzoyl)pyrrolidin-2-one 在 selenium 一氧化碳 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、506.62 kPa 条件下， 反应 15.0h， 以98%的产率得到2,3-dihydro-1-methylpyrrolo<2,1-b>quinazolin-9(1H)-one
  参考文献：
  名称：

  Synthesis of 3,4-dihydroquinazolin-4-one: selenium-catalyzed reductive N-heterocyclization of N-(2-nitrobenzoyl)amides with carbon monoxide

  摘要：

  A catalytic synthetic method of 3,4-dihydroquinazolin-4-ones has been developed. When N-(2-nitrobenzoyl)amides were treated with carbon monoxide in the presence of a catalytic amount of selenium, reductive N-heterocyclization of N-(2-nitrobenzoyl)amide efficiently proceeded to give the corresponding 3,4-dihydroquinazolin-4-ones in moderate to good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00035-7

文献信息

• Nitrogen bridgehead compounds. 66. Bronchodilator nitrogen bridgehead compounds with a pyrimidinone moiety
  作者：Istvan Hermecz、Lelle Vasvari-Debreczy、Agnes Horvath、Maria Balogh、Jozsef Kokosi、Christine DeVos、Ludovic Rodriguez

  DOI：10.1021/jm00392a003

  日期：1987.9

  New types of bronchodilator agents, bi- and tricyclic nitrogen bridgehead compounds with a pyrimidin-4(3H)-one ring, were synthesized and evaluated for bronchodilator activity against serotonin-, histamine-, and acetylcholine-induced spasms in the guinea pig Konzett-Rössler test. The structure-activity relationships are discussed. The effects of some bi- and tricyclic derivatives on the human bronchus

  合成了新型的支气管扩张剂，即具有嘧啶4（3H）-环的双环和三环氮桥头化合物，并评估了其对豚鼠Konzett-中血清素，组胺和乙酰胆碱诱导的痉挛的支气管扩张活性。 Rössler测试。讨论了构效关系。还研究了一些双环和三环衍生物对人支气管的影响。在分离的豚鼠回肠和气管上测试了同源的三环化合物68和69，并在毛果芸香碱处理的狗中研究了化合物69的作用。选择Azepino [2,1-b]喹唑啉（69; CHINOIN-1289）进行进一步的生化和临床研究。
• Proton‐ and halogen‐induced cyclizations of 2‐(3‐butenyl)quinazolin‐4( <scp>3</scp> H)‐ones in the synthesis of pyrrolo[2,1‐ <i>b</i> ]‐ and pyrrolo[1,2‐ <i>а</i> ]quinazolinone derivatives
  作者：Ruslan I. Vaskevych、Nataliia O. Savinchuk、Alla I. Vaskevych、Eduard B. Rusanov、Denys V. Bylina、Andrii A. Kyrylchuk、Mykhailo V. Vovk

  DOI：10.1002/jhet.4598

  日期：2023.3

  With the aim of finding efficient initiators for electrophilic cyclizations of 2-(3-butenyl)quinazolin-4(3H)-ones, their reactions with a number of acids (НCl, CF3COOH, H2SO4, polyphosphoric acid, CF3SO2OH) and halogenating agents (I2, Br2, NIS, NBS) have been studied. As established, CF3SO2OH can be successfully applied in the synthesis of linear 1-methyl-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-ones

  为了寻找 2-(3-butenyl)quinazolin-4(3H)-ones 亲电环化的有效引发剂，它们与许多酸（НCl、CF3COOH、H2SO4、多磷酸、CF3SO2OH）和卤化剂的反应（ I2、Br2、NIS、NBS) 已被研究。正如所确定的那样，CF3SO2OH 可以成功地应用于线性 1-methyl-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-ones 的合成，而使用 I2、NIS 或 NBS 很容易导致角 1-(halomethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones。
• Dunn, A. D.; Kinnear, K. I., Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 53 - 57
  作者：Dunn, A. D.、Kinnear, K. I.

  DOI：——

  日期：——
• US8501786B2
  申请人：——

  公开号：US8501786B2

  公开（公告）日：2013-08-06
• Synthesis of 3,4-dihydroquinazolin-4-one: selenium-catalyzed reductive N-heterocyclization of N-(2-nitrobenzoyl)amides with carbon monoxide
  作者：Yutaka Nishiyama、Masaharu Hirose、Wataru Kitagaito、Noboru Sonoda

  DOI：10.1016/s0040-4039(02)00035-7

  日期：2002.3

  A catalytic synthetic method of 3,4-dihydroquinazolin-4-ones has been developed. When N-(2-nitrobenzoyl)amides were treated with carbon monoxide in the presence of a catalytic amount of selenium, reductive N-heterocyclization of N-(2-nitrobenzoyl)amide efficiently proceeded to give the corresponding 3,4-dihydroquinazolin-4-ones in moderate to good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.