8-(2-propen-1-yl)-2H-1,4-benzoxazin-3(4H)-one | 876921-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 8-(2-propen-1-yl)-2H-1,4-benzoxazin-3(4H)-one
• 英文别名: 8-Allyl-2H-benzo[b][1,4]oxazin-3(4H)-one；8-prop-2-enyl-4H-1,4-benzoxazin-3-one
• CAS: 876921-17-4
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: HNQCTKVOLVBTCG-UHFFFAOYSA-N

物化性质

• 沸点：
  364.7±42.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-(2-propen-1-yl)-2H-1,4-benzoxazin-3(4H)-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以88%的产率得到8-(2-propen-1-yl)-2H-1,4-benzoxazine-3(4H)-thione
  参考文献：
  名称：

  [EN] FUSED TRICYCLIC DERIVATIVES FOR THE TREATMENT OF PSYCHOTIC DISORDERS
  [FR] DERIVES TRICYCLIQUES ACCOLES POUR LE TRAITEMENT DE TROUBLES PSYCHOTIQUES

  摘要：

  式中R1、R2、X、A、Y、B、Z1、Q、p、r和s在说明书中定义的用于治疗精神疾病、抑郁障碍、焦虑障碍和性功能障碍的(I)式化合物。

  公开号：

  WO2006024517A1
• 作为产物：
  描述：

  methyl {[2-nitro-6-(2-propen-1-yl)phenyl]oxy}acetate 在 铁粉 、 氯化铵 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以68%的产率得到8-(2-propen-1-yl)-2H-1,4-benzoxazin-3(4H)-one
  参考文献：
  名称：

  8- [2-（4-芳基-1-哌嗪基）乙基] -2 H -1,4-苯并恶嗪-3（4 H）-ones：双作用5-HT 1受体拮抗剂和5-羟色胺再摄取抑制剂，第二部分

  摘要：

  8- [2-（4-芳基-1-哌嗪基）乙基] -2 H -1,4-苯并恶嗪-3（4 H）-已被确定为具有下列作用的强效5-HT 1A / B / D受体拮抗剂并且在hERG钾离子通道上没有其他SerT活性和高度选择性。对不同靶标活性的调节使化合物具有适合进一步体内表征的一系列特征。

  DOI：

  10.1016/j.bmcl.2009.02.056

文献信息

• FUSED TRICYCLIC DERIVATIVES FOR THE TREATMENT OF PSYCHOTIC DISORDERS
  申请人：Bentley Jonathan

  公开号：US20120022056A1

  公开（公告）日：2012-01-26

  Compounds of formula (I) wherein R 1 , R 2 , X, A, Y, B, Z 1 , Q, p, r and s are defined in the specification for treating inter alia psychotic disorders, depressive disorders, anxiety disorders and sexual dysfunctions.

  式(I)中的化合物，其中R1、R2、X、A、Y、B、Z1、Q、p、r和s在规范中定义，用于治疗精神疾病、抑郁症、焦虑症和性功能障碍等疾病。
• Design and Synthesis of Novel Tricyclic Benzoxazines as Potent 5-HT_1A/B/D Receptor Antagonists Leading to the Discovery of 6-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}-4<i>H</i>-imidazo[5,1-<i>c</i>][1,4]benzoxazine-3-carboxamide (GSK588045)
  作者：Steven M. Bromidge、Roberto Arban、Barbara Bertani、Silvia Bison、Manuela Borriello、Paolo Cavanni、Giovanna Dal Forno、Romano Di-Fabio、Daniele Donati、Stefano Fontana、Massimo Gianotti、Laurie J. Gordon、Enrica Granci、Colin P. Leslie、Luca Moccia、Alessandra Pasquarello、Ilaria Sartori、Anna Sava、Jeannette M. Watson、Angela Worby、Laura Zonzini、Valeria Zucchelli

  DOI：10.1021/jm100482n

  日期：2010.8.12

  Bioisoteric replacement of the metabolically labile N-methyl amide group of a series of benzoxazinones with small heterocyclic rings has led to novel series of fused tricyclic benzoxazines which are potent 5-HT1A/B/D receptor antagonists with and without concomitant human serotonin transporter (hSerT) activity. Optimizing against multiple parameters in parallel identified 6-2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}-4H-imidazo[5,1-c][1,4]benzoxazine-3-carboxamide (GSK588045) as a potent 5-HT1A/B/D receptor antagonist with a high degree of selectivity over human ether-a-go-go related gene (hERG) potassium channels, favorable pharmacokinetics, and excellent activity in vivo in rodent pharmacodynamic (PD) models. On the basis of its outstanding overall profile, this compound was progressed as a clinical candidate with the ultimate aim to assess its potential as a faster acting antidepressant/anxiolytic with reduced side-effect burden.
• [EN] FUSED TRICYCLIC DERIVATIVES FOR THE TREATMENT OF PSYCHOTIC DISORDERS<br/>[FR] DERIVES TRICYCLIQUES ACCOLES POUR LE TRAITEMENT DE TROUBLES PSYCHOTIQUES
  申请人：GLAXO GROUP LTD

  公开号：WO2006024517A1

  公开（公告）日：2006-03-09

  Compounds of formula (I) wherein R1, R2, X, A, Y, B, Z1, Q, p, r and s are defined in the specification for treating inter alia psychotic disorders, depressive disorders, anxiety disorders and sexual dysfunctions.

  式中R1、R2、X、A、Y、B、Z1、Q、p、r和s在说明书中定义的用于治疗精神疾病、抑郁障碍、焦虑障碍和性功能障碍的(I)式化合物。
• 8-[2-(4-Aryl-1-piperazinyl)ethyl]-2H-1,4-benzoxazin-3(4H)-ones: Dual-acting 5-HT1 receptor antagonists and serotonin reuptake inhibitors—Part II
  作者：Steven M. Bromidge、Barbara Bertani、Manuela Borriello、Andrea Bozzoli、Stefania Faedo、Massimo Gianotti、Laurie J. Gordon、Matthew Hill、Valeria Zucchelli、Jeannette M. Watson、Laura Zonzini

  DOI：10.1016/j.bmcl.2009.02.056

  日期：2009.4

  8-[2-(4-Aryl-1-piperazinyl)ethyl]-2H-1,4-benzoxazin-3(4H)-ones have been identified as highly potent 5-HT1A/B/D receptor antagonists with and without additional SerT activity and a high degree of selectivity over hERG potassium channels. Modulation of the different target activities gave compounds with a range of profiles suitable for further in vivo characterization.

  8- [2-（4-芳基-1-哌嗪基）乙基] -2 H -1,4-苯并恶嗪-3（4 H）-已被确定为具有下列作用的强效5-HT 1A / B / D受体拮抗剂并且在hERG钾离子通道上没有其他SerT活性和高度选择性。对不同靶标活性的调节使化合物具有适合进一步体内表征的一系列特征。