6-chloro-3-methyl-3,4-dihydro-1H-quinoxalin-2-one | 168173-69-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-chloro-3-methyl-3,4-dihydro-1H-quinoxalin-2-one
• 英文别名: 6-chloro-3-methyl-3,4-dihydroquinoxalin-2(1H)-one；(3RS)-6-Chloro-3-methyl-3,4-dihydroquinoxalin-2(1H)-one
• CAS: 168173-69-1
• 化学式: C₉H₉ClN₂O
• 分子量: 196.636
• InChiKey: PWSMFPODKQXVKB-UHFFFAOYSA-N

物化性质

• 沸点：
  379.1±42.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-3-methyl-3,4-dihydro-1H-quinoxalin-2-one 在 sodium hydroxide 、 双氧水 作用下， 以 水 为溶剂， 反应 6.0h， 以83%的产率得到6-chloro-3-methyl-1H-quinoxalin-2-one
  参考文献：
  名称：

  Novel Approach to 3‐Methyl‐1H‐quinoxalin‐2‐ones

  摘要：

  A novel approach to the synthesis of 3-methyl-1H-quinoxalin-2-ones has been described. These compounds were regioselectively prepared by starting from substituted phenylamines and alpha-chloropropionyl chloride through the efficient procedures of acylation, nitration, reduction, intramolecular alkylation, and oxidation.

  DOI：

  10.1080/00397910500213880
• 作为产物：
  描述：

  2-chloro-N-(4-chloro-2-nitrophenyl)propanamide 在 ammonium chloride 、 铁粉 、 碳酸氢钠 、 溶剂黄146 、 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.25h， 生成 6-chloro-3-methyl-3,4-dihydro-1H-quinoxalin-2-one
  参考文献：
  名称：

  Novel Approach to 3‐Methyl‐1H‐quinoxalin‐2‐ones

  摘要：

  A novel approach to the synthesis of 3-methyl-1H-quinoxalin-2-ones has been described. These compounds were regioselectively prepared by starting from substituted phenylamines and alpha-chloropropionyl chloride through the efficient procedures of acylation, nitration, reduction, intramolecular alkylation, and oxidation.

  DOI：

  10.1080/00397910500213880

文献信息

• Synthesis and biological evaluation of novel quinoxalinone-based HIV-1 reverse transcriptase inhibitors
  作者：Jie Zhou、Mingyu Ba、Bo Wang、Haibo Zhou、Jianbo Bie、Decai Fu、Yingli Cao、Bailing Xu、Ying Guo

  DOI：10.1039/c3md00337j

  日期：——

  A series of novel N4-substituted thiophen-3-ylsulfonylquinoxalinone derivatives were designed and synthesized by variations of 2- and 5-position of the thiophene ring. All target molecules were tested for their anti-HIV-1 replication activities and compounds 1b and 1d were found to be the most potent inhibitors with an IC50 value at 10−8 mol L−1 level. The preliminary structure–activity relationships

  通过改变噻吩环的2-和5-位，设计和合成了一系列新颖的N 4-取代的噻吩-3-基磺酰基喹喔啉酮衍生物。测试所有靶分子的抗HIV-1复制活性，发现化合物1b和1d是最有效的抑制剂，IC 50值为10 -8 mol L -1。根据CDOCKER预测的化合物1b的结合模式，分析了初步的结构活性关系。
• Chinoxaline, Verfahren zu ihrer Herstellung und ihre Verwendung
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0509398A1

  公开（公告）日：1992-10-21

  Verbindungen der Formel I bzw. Ia in der n und die Substituenten R¹ - R⁵ sowie X die genannte Bedeutung haben, weisen eine antivirale Wirksamkeit auf.

  式 I 或 Ia 的化合物 其中 n 和取代基 R¹ - R⁵ 及 X 如上文所定义，具有抗病毒活性。
• Synthesis and biological evaluation of N4-(hetero)arylsulfonylquinoxalinones as HIV-1 reverse transcriptase inhibitors
  作者：Bailing Xu、Yan Sun、Ying Guo、Yingli Cao、Tao Yu

  DOI：10.1016/j.bmc.2009.02.039

  日期：2009.4

  A series of novel N-4-(hetero) arylsulfonylquinoxalinone derivatives were prepared in a straight and efficient way. Of all the synthesized compounds, five compounds exhibited potent anti-HIV-1 replication activities with IC50 value at the level of 10(-7) mol/L. Preliminary structure-activity relationships were studied in details and that will shed light on the discovery of more potent non-nucleoside reverse-transcriptase inhibitors. (c) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of Substituted 1,3-Dimethyl-1H-quinoxalin-2-ones from Aniline Derivatives
  作者：Xun Li、Donghua Wang、Jifeng Wu、Wenfang Xu

  DOI：10.3987/com-05-10461

  日期：——

  Substituted 1,3-dimethyl-1H-quinoxalin-2-ones (7) have been synthesized through the procedures of acylation, nitration, reduction, intramolecular alkylation, oxidation, and N-methylation starting from 3,4-disubstituted aniline.
• Kombinationspräparate, enthaltend ein Chinoxalin und ein Nukleosid
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP0657166B1

  公开（公告）日：2003-04-09