7-chloro-2,2,4-trimethyl-1,2-dihydroquinoline | 1810-73-7

• 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: 7-chloro-2,2,4-trimethyl-1,2-dihydroquinoline
• 英文别名: 7-chloro-2,2,4-trimethyl-1H-quinoline
• CAS: 1810-73-7
• 化学式: C₁₂H₁₄ClN
• 分子量: 207.703
• InChiKey: WGIMEYSRVQFMGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  7-chloro-2,2,4-trimethyl-1,2-dihydroquinoline 在 咪唑 、 正丁基锂 、 硼烷四氢呋喃络合物 、 溴 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Cyclopentaquinoline Derivatives as Nonsteroidal Glucocorticoid Receptor Antagonists

  摘要：

  The steroidal glucocorticoid antagonist mifepristone has been reported to improve the symptoms of depression. We report the discovery of 6-(3,5-dimethylisoxazol-4-yl)-2,2,4,4-tetramethyl-2,3,4,7,8,9-hexahydro-1H-cyclopenta[h]quinolin-3-one 3d (QCA-1093) as a novel nonsteroidal glucocorticoid receptor antagonist. The compound displayed potent in vitro activity, high selectivity Over other steroid hormone receptors, and significant antidepressant-like activity in vivo.

  DOI：

  10.1021/jm501758q
• 作为产物：
  描述：

  4-甲基-3戊烯-2-酮 、 3-氯苯胺 在 indium(III) chloride 、 silica gel 作用下， 反应 0.42h， 以73%的产率得到7-chloro-2,2,4-trimethyl-1,2-dihydroquinoline
  参考文献：
  名称：

  Efficient microwave-assisted synthesis of quinolines and dihydroquinolines under solvent-free conditions

  摘要：

  A convenient and efficient procedure for the synthesis of quinolines and dihydroquinolines has been developed by a simple one-pot reaction of anilines with alkyl vinyl ketones on the surface of silica gel impregnated with indium(III) chloride under microwave irradiation without any solvent. (C) 2003 Elsevier Science Ltd. All tights reserved.

  DOI：

  10.1016/s0040-4020(02)01587-9

文献信息

• The p-toluenesulfonic acid catalyzed single pot synthesis of tetracyclic 1,2-dihydroquinolines: a metal free approach
  作者：Anil K. Hajare、Arun R. Jagdale、G. Gautham Shenoy、Neelima Sinha

  DOI：10.1039/c6nj00928j

  日期：——

  A simple, convenient and efficient metal free approach towards the synthesis of polysubstituted 1,2-dihydroquinolines.

  一种简单、方便和高效的无金属方法合成多取代1,2-二氢喹啉。
• A Facile Synthesis of 2,2,4-Trisubstituted-1,2-Dihydroquinolines Catalyzed by Zinc Triflate under Solvent-Free Conditions
  作者：Dhiman Kundu、Shrishnu Kumar Kundu、Adinath Majee、Alakananda Hajra

  DOI：10.1002/jccs.200800175

  日期：2008.10

  An efficient process has been developed for the synthesis of 2,2,4-trisubstituted-1,2-dihydroquinolines in good yields through a simple one-pot condensation between anilines and ketones in the presence of zinc triflate as a catalyst at room temperature under solvent-free conditions.

  在三氟甲磺酸锌作为催化剂的条件下，在室温下，苯胺和酮之间的简单一锅缩合反应，开发了一种高效合成 2,2,4-三取代-1,2-二氢喹啉的方法。无溶剂条件。
• Scope and Mechanistic Study of the Ruthenium-Catalyzed<i> ortho</i>-C−H Bond Activation and Cyclization Reactions of Arylamines with Terminal Alkynes
  作者：Chae S. Yi、Sang Young Yun

  DOI：10.1021/ja055608s

  日期：2005.12.1

  was found to be a highly effective catalyst for the C-H bond activation reaction of arylamines and terminal alkynes. The regioselective catalytic synthesis of substituted quinoline and quinoxaline derivatives was achieved from the ortho-C-H bond activation reaction of arylamines and terminal alkynes by using the catalyst Ru(3)(CO)(12)/HBF(4).OEt(2). The normal isotope effect (k(CH)/k(CD) = 2.5) was

  阳离子氢化钌配合物 [(PCy(3))(2)(CO)(CH(3)CN)(2)RuH](+)BF(4)(-) 被发现是一种高效的催化剂芳胺和末端炔烃的 CH 键活化反应。通过使用催化剂 Ru(3)(CO)(12)/HBF(4).OEt(2)，芳胺和末端炔烃的邻位 CH 键活化反应实现了取代喹啉和喹喔啉衍生物的区域选择性催化合成。观察到 C(6)H(5)NH(2) 和 C(6)D(5)NH(2) 与丙炔反应的正常同位素效应 (k(CH)/k(CD) = 2.5) . 从一系列间位取代苯胺、m-XC(6)H(4)NH(2) 与 sigma(p) 的相对速率的相关性中获得高度负的哈米特值 (rho = -4.4) Ru(3)(CO)(12)/HBF(4).OEt(2)（3 mol % Ru，1:3 摩尔比）的存在。二氢吲哚和无环芳胺与 DCPh 反应的氘标记研究表明，炔烃 CH 键活化步骤是可逆的
• Bidentate Ligand Driven Intramolecularly Te…O Bonded Organotellurium Cations from Synthesis, Stability to Catalysis
  作者：Saket Jain、Saurabh Sandip Satpute、Raushan Kumar Jha、Mili Sanjeev Patel、Sangit Kumar

  DOI：10.1002/chem.202303089

  日期：2024.1.16

  method using diaryl ditelluride. Further, monotellurides were converted into corresponding tellurium cations. Next, these Lewis acidic tellurium cations were used as catalysts to synthesize 1,2-dihydroquinolines from anilines and highly regioselective creation of β-amino alcohols from epoxides.

  以二芳基二碲化物为原料，通过铜催化法合成了一系列由2- N- (喹啉-8-基)苯甲酰胺衍生的新型不对称苯基碲化物。此外，单碲化物被转化为相应的碲阳离子。接下来，这些路易斯酸性碲阳离子被用作催化剂，从苯胺合成1,2-二氢喹啉，并从环氧化物高度区域选择性地生成β-氨基醇。
• Discovery of Novel Potent Reversible and Irreversible Myeloperoxidase Inhibitors Using Virtual Screening Procedure
  作者：Jalal Soubhye、Ibaa Chikh Alard、Iyas Aldib、Martine Prévost、Michel Gelbcke、Annelise De Carvalho、Paul G. Furtmüller、Christian Obinger、Jörg Flemmig、Sara Tadrent、Franck Meyer、Alexandre Rousseau、Jean Nève、Véronique Mathieu、Karim Zouaoui Boudjeltia、François Dufrasne、Pierre Van Antwerpen

  DOI：10.1021/acs.jmedchem.7b00285

  日期：2017.8.10

  The heme enzyme myeloperoxidase (MPO) participates in innate immune defense mechanism through formation of microbicidal reactive oxidants. However, evidence has emerged that MPO-derived oxidants contribute to propagation of inflammatory diseases. Because of the deleterious effects of circulating MPO, there is a great interest in the development of new efficient and specific inhibitors. Here, we have performed a novel virtual screening procedure, depending on ligand-based pharmacophore modeling followed by structure-based virtual screening. Starting from a set of 727842 compounds, 28 molecules were selected by this virtual method and tested on MPO in vitro. Twelve out of 28 compounds were found to have an IC50 less than 5 mu M. The best inhibitors were 2-(7-methoxy-4-methylquinazolin-2-yl)guanidine (28) and (R)-2-(14(2,3-dihydro-1H-imidazol-2-yl-methyl)pyrrolidin-3-yl)-5-fluoro-1H-benzo[d]imidazole (42) with IC50 values of 44 and 50 nM, respectively. Studies on the mechanism of inhibition suggest that 28 is the first potent mechanism-based inhibitor and inhibits irreversibly MPO at nanomolar concentration.