(2-氯-5,8-二甲基-3-喹啉基)甲醇 | 485337-91-5

• 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
• 中文名称: (2-氯-5,8-二甲基-3-喹啉基)甲醇
• 英文名称: (2-chloro-5,8-dimethylquinolin-3-yl)methanol
• 英文别名: 2-Chloro-5,8-dimethylquinoline-3-methanol
• CAS: 485337-91-5
• 化学式: C₁₂H₁₂ClNO
• 分子量: 221.686
• InChiKey: IANOUAKORKRCMR-UHFFFAOYSA-N

物化性质

• 沸点：
  381.5±37.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-氯-5,8-二甲基-3-喹啉基)甲醇 在 四(三苯基膦)钯 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 1,10-菲罗啉 、 potassium carbonate 、 乙二醇 作用下， 反应 2.66h， 生成 (E)-7-chloro-4-((5,8-dimethyl-2-phenylquinolin-3-yl)methylene)-9-phenyl-3,4-dihydroacridin-1(2H)-one
  参考文献：
  名称：

  Ir（I）通过顺序Suzuki-Miyaura偶联，脱氢Friedländer反应和sp3-C-H活化催化合成（E）-4-苄基yl啶和（E）-2-苯乙烯基喹啉-3-羧酰胺

  摘要：

  描述了一种由二铱（I）催化的DES介导的（E）-4-苄叉基ac啶-1（2H）-（E）-2-苯乙烯基喹啉3-羧酰胺的三（或）四组分单罐组装。该方法涉及在单个反应容器中连续形成三个碳-碳键和一个碳-氮键。此外，已经建立了克级合成法和详细的机理研究。

  DOI：

  10.1002/ejoc.202000834
• 作为产物：
  描述：

  2-氯-5,8-二甲基-3-喹啉甲醛 在 sodium tetrahydroborate 作用下， 生成 (2-氯-5,8-二甲基-3-喹啉基)甲醇
  参考文献：
  名称：

  通过铜-TEMPO催化的脱氢，2-卤代喹啉基酮的sp2-CH官能化（S8的亲核硫醇化）反应轻松合成2-酰基噻吩并[2,3-b]喹啉。

  摘要：

  据报道，2-卤代喹啉基酮通过Cu-TEMPO催化的脱氢反应，sp2-CH官能化（使用元素硫作为硫醇替代物（硫源）和甲硫氨酸）有效，无溶剂地合成了2-酰基噻吩并[2,3-b]喹啉。乙酸四丁铵作为离子反应介质。优化的反应条件在温和的反应条件下具有优异的化学选择性和宽泛的官能团耐受性，可提供优异的产品收率。弗里德兰德环化，还原和烯烃官能化反应进一步展示了合成分子的合成重要性。

  DOI：

  10.1021/acs.orglett.9b04598

文献信息

• Substituted Pyrrolidines and Methods of Use
  申请人：AbbVie S.à.r.l.

  公开号：US20180099932A1

  公开（公告）日：2018-04-12

  The invention discloses compounds of Formula (I) wherein R 1 , R 2 , R 2A , R 3 , R 3A , R 4 , and R 5 are as defined herein. The present invention relates to compounds and their use in the treatment of cystic fibrosis, methods for their production, pharmaceutical compositions comprising the same, and methods of treating cystic fibrosis by administering a compound of the invention.

  本发明涉及一种具有以下结构的化合物（I），其中R1、R2、R2A、R3、R3A、R4和R5如本文所定义。本发明涉及这些化合物及其在囊性纤维化治疗中的应用，以及它们的生产方法，包含它们的药物组合物，以及通过给予该发明的化合物来治疗囊性纤维化的方法。
• Facile Synthesis of 2-Acylthieno[2,3-<i>b</i>]quinolines via Cu-TEMPO-Catalyzed Dehydrogenation, sp²-C–H Functionalization (Nucleophilic Thiolation by S₈) of 2-Haloquinolinyl Ketones
  作者：Chitrala Teja、Fazlur Rahman Nawaz Khan

  DOI：10.1021/acs.orglett.9b04598

  日期：2020.3.6

  An efficient, solvent-free synthesis of 2-acylthieno[2,3-b]quinolines is reported from 2-halo-quinolinyl ketones through Cu-TEMPO catalyzed dehydrogenation, sp2-C-H functionalization using elemental sulfur as thiol surrogate (sulfur source) and tetrabutylammonium acetate as an ionic reaction medium. The optimized reaction conditions give excellent product yields under mild reaction conditions with

  据报道，2-卤代喹啉基酮通过Cu-TEMPO催化的脱氢反应，sp2-CH官能化（使用元素硫作为硫醇替代物（硫源）和甲硫氨酸）有效，无溶剂地合成了2-酰基噻吩并[2,3-b]喹啉。乙酸四丁铵作为离子反应介质。优化的反应条件在温和的反应条件下具有优异的化学选择性和宽泛的官能团耐受性，可提供优异的产品收率。弗里德兰德环化，还原和烯烃官能化反应进一步展示了合成分子的合成重要性。
• Ir(I)‐Catalyzed Synthesis of ( <i>E</i> )‐4‐Benzylidenylacridines and ( <i>E</i> )‐2‐Styrylquinoline‐3‐carboxamide through Sequential Suzuki–Miyaura Coupling, Dehydrogenative Friedländer Reaction, and sp ³ ‐C–H Activation
  作者：Soda Prameela、Fazlur‐Rahman Nawaz Khan

  DOI：10.1002/ejoc.202000834

  日期：2020.9.7

  DESs mediated three (or) four‐component one‐pot assembly of (E)‐4‐benzylidenylacridin‐1(2H)‐ones (E)‐2‐styryl quinoline‐3‐carboxamides is described. The method involves the consecutive three carbon–carbon and one carbon–nitrogen bond formation in a single reaction vessel. Moreover, gram scale synthesis and detailed mechanistic study have been established.

  描述了一种由二铱（I）催化的DES介导的（E）-4-苄叉基ac啶-1（2H）-（E）-2-苯乙烯基喹啉3-羧酰胺的三（或）四组分单罐组装。该方法涉及在单个反应容器中连续形成三个碳-碳键和一个碳-氮键。此外，已经建立了克级合成法和详细的机理研究。
• Triazolothiadizepinylquinolines as potential MetAP-2 and NMT inhibitors: Microwave-assisted synthesis, pharmacological evaluation and molecular docking studies
  作者：Saba Kauser J. Shaikh、Ravindra R. Kamble、Praveen K. Bayannavar、Shilpa M. Somagond、Shrinivas D. Joshi

  DOI：10.1016/j.molstruc.2019.127445

  日期：2020.3

  The enzymes MetAP-2 and NMT play a crucial role in the process of myristoylation of oncoproteins which is deregulated in many types of cancers. Execution of both these enzymes is considered as strategy for the intervention of various cancers and relative fungal infections, and hence the discovery of novel MetAP-2 and NMT inhibitors necessitate their high relevancy. In this investigation, we have synthesized a series of novel seven-membered triazolothiadiazepinyl quinolines 10(a-m) distinctively under microwave irradiation technique and identified as selective MetAP-2 and NMT inhibitors. Amongst the functionalized derivatives when evaluated for the in vitro antifungal assay, compounds 10b, 10c, 10e and 10f were considered promising due to notable inhibitory effects (MIC = 0.2 mg/mL) on Aspergillus fumigatus. Screening of the anticancer activity against NCI-60 Human tumor cell lines portrayed that conjugates 10b, 10c, 10e and 10f were found to be moderately effective against the Renal Cancer cell line UO-31. The data acquired from biological studies was further validated by molecular docking studies and p harmaco kinetic evaluation. (C) 2019 Elsevier B.V. All rights reserved.