6-phenyl-3,4-dihydroquinolin-2(1H)-one | 736156-15-3

• 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: 6-phenyl-3,4-dihydroquinolin-2(1H)-one
• 英文别名: 6-phenyl-3,4-dihydro-1H-quinolin-2-one
• CAS: 736156-15-3
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: KSNHCIKVXXKDJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-phenyl-3,4-dihydroquinolin-2(1H)-one 在 劳森试剂 、 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.25h， 生成 6-phenyl-1-(3-oxopentyl)-3,4-dihydroquinolin-2(1H)-thione
  参考文献：
  名称：

  Synthesis, Biological Activity, and Three-Dimensional Quantitative Structure−Activity Relationship Model for a Series of Benzo[c]quinolizin-3-ones, Nonsteroidal Inhibitors of Human Steroid 5α-Reductase 1

  摘要：

  New 5alpha-reductase 1 (5alphaR-1) inhibitors were designed to complete a consistent set of analogues suitable for a 3D QSAR study. These compounds were synthesized by a modification of the aza-Robinson annulation, further functionalized by Pd-catalyzed cross-coupling processes, and were tested with human 5alphaR-1 expressed in Chinese hamster ovary 1827 cells. It turned out that the potency of the resulting inhibitors was strongly dependent on the type of substitution at the 8 position, with the IC50 values ranging from 8.1 to 1050 nM. The construction of this homogeneous set of molecules allowed a 3D QSAR study. In particular, comparative molecular field analysis (CoMFA) was used to correlate the potency of the inhibitors with their physicochemical features. Highly accurate evaluations of the atomic point charges were carried out by means of quantum chemical calculations at the DFT/B3LYP level of theory followed by the RESP fitting procedure. It turned out that increasing the reliability of electrostatic parameters greatly affected the statistical results of the QSAR analysis. The 3D QSAR model proposed could be very useful in the further development of 5alphaR-1 inhibitors, which are suitable candidates to be evaluated as drugs in the treatment of 5alphaR-1 related diseases such as acne and alopecia in men and hirsutism in women.

  DOI：

  10.1021/jm031131o
• 作为产物：
  描述：

  4-氨基联苯 在 三氯化铝 作用下， 以 丙酮 为溶剂， 反应 7.0h， 生成 6-phenyl-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis, Biological Activity, and Three-Dimensional Quantitative Structure−Activity Relationship Model for a Series of Benzo[c]quinolizin-3-ones, Nonsteroidal Inhibitors of Human Steroid 5α-Reductase 1

  摘要：

  New 5alpha-reductase 1 (5alphaR-1) inhibitors were designed to complete a consistent set of analogues suitable for a 3D QSAR study. These compounds were synthesized by a modification of the aza-Robinson annulation, further functionalized by Pd-catalyzed cross-coupling processes, and were tested with human 5alphaR-1 expressed in Chinese hamster ovary 1827 cells. It turned out that the potency of the resulting inhibitors was strongly dependent on the type of substitution at the 8 position, with the IC50 values ranging from 8.1 to 1050 nM. The construction of this homogeneous set of molecules allowed a 3D QSAR study. In particular, comparative molecular field analysis (CoMFA) was used to correlate the potency of the inhibitors with their physicochemical features. Highly accurate evaluations of the atomic point charges were carried out by means of quantum chemical calculations at the DFT/B3LYP level of theory followed by the RESP fitting procedure. It turned out that increasing the reliability of electrostatic parameters greatly affected the statistical results of the QSAR analysis. The 3D QSAR model proposed could be very useful in the further development of 5alphaR-1 inhibitors, which are suitable candidates to be evaluated as drugs in the treatment of 5alphaR-1 related diseases such as acne and alopecia in men and hirsutism in women.

  DOI：

  10.1021/jm031131o

文献信息

• FUSED HETEROCYCLIC COMPOUNDS AS ION CHANNEL MODULATORS
  申请人：Abelman Matthew

  公开号：US20100113514A1

  公开（公告）日：2010-05-06

  The present invention relates to sodium channel inhibitors of Formula : in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are as defined above, and to their use in the treatment of various disease states, including cardiovascular diseases and diabetes.

  本发明涉及Formula的钠通道抑制剂：其中R1、R2、R3、R4、R5、R6和R7如上定义，并其在治疗各种疾病状态中的应用，包括心血管疾病和糖尿病。
• Iron‐Catalyzed Intramolecular Arene C(sp ² )−H Amidations under Mechanochemical Conditions
  作者：Peng Shi、Yongliang Tu、Deshen Kong、Peng Wu、Ding Ma、Carsten Bolm

  DOI：10.1002/anie.202204874

  日期：2022.7.25

  mechanochemical approach towards 3,4-dihydro-2(1H)-quinolinones by catalysis with FeBr3 has been developed. The solvent-free processes start from readily available dioxazolones, which undergo intramolecular amidation reactions providing the products in good to very high yields. Practically, the reactions are easy to perform, proceed within a short period of time and require only standard ball milling equipment

  开发了一种通过 FeBr 3催化制备 3,4-二氢-2(1 H )-喹啉酮的机械化学方法。无溶剂工艺从容易获得的二恶唑酮开始，它经历分子内酰胺化反应，以良好到非常高的产率提供产品。实际上，反应很容易进行，在短时间内进行，并且只需要标准的球磨设备。
• Nitrenium ion-based ipso-addition and ortho-cyclization of arenes under photo and iron dual-catalysis
  作者：Miaofeng Ren、Xiaoyang Yan、Xiaojing Lai、Jin-Biao Liu、Hongwei Zhou、Guanyinsheng Qiu

  DOI：10.1016/j.mcat.2022.112413

  日期：2022.8

  developed as an efficient acyl nitrenium ion precursor. An iron-catalyzed acyl nitrenium-based ipso-addition and ortho-cyclization of arenes under photocatalysis is reported for the switchable synthesis of 3,4-dihydroquinolin-2-ones and 6,9-diene-2,8-diones. In the reaction, FeCl3 serves as the photocatalyst and SET reductant, and an acyl nitrenium ion was proposed as a key intermediate. It is assumed that

  在这项工作中，N-酰氧基苯甲酰胺被开发为一种高效的酰基氮鎓离子前体。报道了在光催化下基于铁催化的酰基硝基的ipso加成和芳烃的邻位环化，用于可转换地合成 3,4-dihydroquinolin-2-one 和 6,9-diene-2,8-diones。在该反应中，FeCl 3作为光催化剂和 SET 还原剂，提出了一个酰基氮鎓离子作为关键中间体。假设 ipso 加成和邻环化的差异是由底物上的取代基实现的。对位取代芳烃的反应主要通过ipso加成和 CC迁移，而间位取代芳烃的迁移通过邻环化进行。
• 10.1021/acs.orglett.4c02348
  作者：Cao, Zhi-Wei、Zhang, Ji-Xuan、Wang, Jin-Tao、Li, Lang、Chen, Xiao-Yue、Jin, Shengnan、Cao, Zhong-Yan、Wang, Peng

  DOI：10.1021/acs.orglett.4c02348

  日期：——

  Here, we demonstrate palladium-catalyzed Hiyama-type cross-coupling reactions of aryl thianthrenium or phenoxathiinium salts. By employing stable and inexpensive organosilanes, the arylation, alkenylation, and alkynylation were realized in high efficiency using commercially available Pd(tBu3P)2 as the catalyst, thus providing a reliable method for preparation of biaryls, styrenes, and aryl acetylenes

  在这里，我们演示了芳基噻啉鎓盐或吩恶噻鎓盐的钯催化桧山型交叉偶联反应。通过使用稳定且廉价的有机硅烷，以市售Pd( t Bu 3 P) 2为催化剂，高效地实现了芳基化、烯基化和炔基化，从而为制备联芳基、苯乙烯和芳基乙炔提供了可靠的方法。在温和条件下具有广泛的官能团耐受性。鉴于以显着的区域选择性方式从简单芳烃中获得芳基噻啉盐或吩噻噻啉盐，该方案还为复杂生物活性支架的后期修饰提供了一种有吸引力的方法。
• US8664379B2
  申请人：——

  公开号：US8664379B2

  公开（公告）日：2014-03-04