2-mercaptobenzo[h]quinoline-3-carbaldehyde | 1146978-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-mercaptobenzo[h]quinoline-3-carbaldehyde
• 英文别名: 2-mercapto-3-formylbenzo[h]quinoline；2-sulfanylidene-1H-benzo[h]quinoline-3-carbaldehyde
• CAS: 1146978-27-9
• 化学式: C₁₄H₉NOS
• 分子量: 239.298
• InChiKey: RDIXQIHIBGIKGU-UHFFFAOYSA-N

物化性质

• 熔点：
  243 °C(Solvent: Methanol)
• 沸点：
  442.9±55.0 °C(predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-mercaptobenzo[h]quinoline-3-carbaldehyde 、 2-溴-4'-氟苯乙酮 在 potassium hydroxide 作用下， 反应 0.53h， 以63%的产率得到benzo[h]thieno[2,3-b]quinoline-9-yl(4-fluorophenyl)methanone
  参考文献：
  名称：

  新型苯并[h]噻吩并[2,3-b]喹啉-9-基（芳基）甲酮衍生物的合成

  摘要：

  通过2-巯基苯并[ h ]喹啉-3-甲醛与苯甲酰溴的反应，以高收率和较短的反应时间合成了苯并[ h ]噻吩并[2,3 - b ]喹啉-9-基（芳基）甲酮的新型衍生物。在基本条件下。所有化合物均使用傅里叶变换红外光谱，1 H核磁共振和13 C核磁共振，光谱数据和元素分析进行表征。

  DOI：

  10.1002/jhet.2637
• 作为产物：
  描述：

  N-乙酰-1-萘胺 在 potassium sulfide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 30.0h， 生成 2-mercaptobenzo[h]quinoline-3-carbaldehyde
  参考文献：
  名称：

  新型苯并[h]噻吩并[2,3-b]喹啉-9-基（芳基）甲酮衍生物的合成

  摘要：

  通过2-巯基苯并[ h ]喹啉-3-甲醛与苯甲酰溴的反应，以高收率和较短的反应时间合成了苯并[ h ]噻吩并[2,3 - b ]喹啉-9-基（芳基）甲酮的新型衍生物。在基本条件下。所有化合物均使用傅里叶变换红外光谱，1 H核磁共振和13 C核磁共振，光谱数据和元素分析进行表征。

  DOI：

  10.1002/jhet.2637

文献信息

• The synthesis of iminothiophenone-fused quinolines and evaluation of their serendipitous reactions
  作者：Morteza Shiri、Zeinab Faghihi、Hossein A. Oskouei、Majid M. Heravi、Shima Fazelzadeh、Behrouz Notash

  DOI：10.1039/c6ra11469e

  日期：——

  The novel synthesis of tricyclic 2-(cyclohexylimino)thieno[2,3-b]quinolin-3(2H)-ones from the reaction of 2-mercaptoquinoline-3-carbaldehydes and isocyanides in methanol without the use of any additive is described. This protocol proceeds with high atom economy through the formation of C–S and C–C bonds and then oxidation via tandem reaction. Moreover, some other remarkable aspects of this reaction

  描述了在不使用任何添加剂的情况下，由2-巯基喹啉-3-甲醛与异氰酸酯在甲醇中反应合成三环2-（环己基氨基）噻吩并[2,3 - b ]喹啉-3（2H）-的新方法。 。该协议通过形成C–S和C–C键，然后通过串联反应进行氧化来实现高原子经济性。此外，还研究了该反应的其他显着方面，例如水解和与芳族胺的三组分反应以产生高度共轭的席夫碱。
• An Efficient, Microwave-Assisted, One-Pot Synthesis of Dioxolano Quinoline/benzo[<i>h</i>]quinolines as Potent Antibacterial Agents
  作者：H. R. Prakash Naik、H. S. Bhojya Naik、T. R. Ravikumar Naik、D. S. Lamani、T. Aravinda

  DOI：10.1080/10426500902797095

  日期：2010.1.29

  Quinolines/benzo[h]quinolines are associated with a broad spectrum of biological activities. In view of this, 3-(1,3-dioxolan-2-yl)quinoline/benzo[h]quinoline-2-thiol/selenols were prepared under microwave irradiation through one-pot reactions, and these quinolines/ benzo[h]quinolines were evaluated for potential antibacterial activity. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
• Synthesis of novel benzo[h]quinolines: Wound healing, antibacterial, DNA binding and in vitro antioxidant activity
  作者：Halehatty R. Prakash Naik、Halehatty S. Bhojya Naik、Thangali R. Ravikumar Naik、H. Raja Naika、K. Gouthamchandra、Riaz Mahmood、B.M. Khadeer Ahamed

  DOI：10.1016/j.ejmech.2008.07.006

  日期：2009.3

  We have characterized a new class of 2-mercapto/2-selenobenzo[h]quinoline-3-carbaldehyde (3/4). Antibacterial potential of these compounds against a wide range of Gram-positive and Gram-negative bacteria was studied. The selenium containing compound 4 showed significant inhibition zone on Staphylococcus aureus (22.76 +/- 0.14), Bacillus subtilis (20.63 +/- 0.24), and Streptococcus pyogenes (19.54 +/- 0.20) over sulfur containing compound 3. To validate the ethnotherapeutic claims of the synthetic compounds in skin diseases, wound healing activity was studied, besides antioxidant activity to understand the mechanism of wound healing. The interaction behavior of these compounds with DNA was investigated by absorption spectra (obtained K-b constant for 3 is 2.7 x 10(5) and for 4 is 3.8 x 10(6)), viscosity, and thermal denaturation studies. Finally, the results show that the DNA intercalated 314 compounds are strong antioxidants; they show significan wound healing activity and protect oxidative DNA damage from harmful free radical reactions. (C) 2008 Elsevier Masson SAS. All rights reserved.
• The Synthesis of New Benzo[<i>h</i>]thieno[2,3-<i>b</i>]quinoline-9-yl(aryl)methanone Derivatives
  作者：Ahmad Poursattar Marjani、Jabbar Khalafy、Azar Rostampoor

  DOI：10.1002/jhet.2637

  日期：2017.1

  Novel derivatives of benzo[h]thieno[2,3‐b]quinoline‐9‐yl(aryl)methanone were synthesized in good yield and short reaction times by reaction of 2‐mercaptobenzo[h]quinoline‐3‐carbaldehyde with phenacyl bromides under basic conditions. All compounds were characterized using Fourier transform infrared, 1H nuclear magnetic resonance and 13C nuclear magnetic resonance, spectral data, and elemental analysis

  通过2-巯基苯并[ h ]喹啉-3-甲醛与苯甲酰溴的反应，以高收率和较短的反应时间合成了苯并[ h ]噻吩并[2,3 - b ]喹啉-9-基（芳基）甲酮的新型衍生物。在基本条件下。所有化合物均使用傅里叶变换红外光谱，1 H核磁共振和13 C核磁共振，光谱数据和元素分析进行表征。