1(2H)-异喹啉酮,3-(4-溴苯基)- | 124394-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 1(2H)-异喹啉酮,3-(4-溴苯基)-
• 英文名称: 3-(4-bromophenyl)isoquinolin-1(2H)-one
• 英文别名: 3-(4-bromo-phenyl)-2H-isoquinolin-1-one；3-(4-bromophenyl)-2H-isoquinolin-1-one
• CAS: 124394-21-4
• 化学式: C₁₅H₁₀BrNO
• 分子量: 300.154
• InChiKey: NFNNUTPVXVJNMY-UHFFFAOYSA-N

物化性质

• 熔点：
  260-261 °C
• 沸点：
  502.1±50.0 °C(Predicted)
• 密度：
  1.497±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1(2H)-异喹啉酮,3-(4-溴苯基)- 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-(4-Bromo-phenyl)-1-(4-methyl-[1,4]diazepan-1-yl)-isoquinoline
  参考文献：
  名称：

  Synthesis of new 3-Arylisoquinolinamines: effect on topoisomerase I inhibition and cytotoxicity

  摘要：

  To investigate the structure-activity relationships of 3-arylisoquinolines, diverse substituted 3-aryisoquinolinamines were synthesized and tested in vitro antitumor activity against four tumor cell lines. Some of the compounds showed potent topoisomerase I inhibitory activity. Docking study of 7d with topoisomerase I-DNA complex was also performed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.001
• 作为产物：
  描述：

  2-碘苯甲酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 ammonium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 108.0h， 生成 1(2H)-异喹啉酮,3-(4-溴苯基)-
  参考文献：
  名称：

  [EN] (AZA-)ISOQUINOLINONE DERIVATIVES
  [FR] DÉRIVÉS DE (AZA-)ISOQUINOLINONE

  摘要：

  公开号：

  WO2014023390A3

文献信息

• Fused pyridine derivatives
  申请人：Eisai Co., Ltd.

  公开号：US06340759B1

  公开（公告）日：2002-01-22

  The present provides a condensed pyridine compound (I) represented by the following formula: (wherein, R2 represents ring A represents benzene ring, pyridine ring, thiophene ring or furan ring; and B represents its pharmaceutically acceptable salt or hydrates thereof, which is a clinically useful medicament having a serotonin antagonism, in particular, that for treating, ameliorating or preventing spastic paralysis or central muscle relaxants for ameliorating myotonia.

  目前提供了一种由以下公式表示的缩合吡啶化合物（I）： （其中，R2代表环A代表苯环、吡啶环、噻吩环或呋喃环；B代表其药学上可接受的盐或其水合物，是一种具有血清素拮抗作用的临床上有用的药物，特别用于治疗、改善或预防痉挛性麻痹或改善肌张力过高的中枢肌肉松弛剂。
• Nickel‐Catalyzed Tandem Reaction of Functionalized Arylacetonitriles with Arylboronic Acids in 2‐MeTHF: Eco‐Friendly Synthesis of Aminoisoquinolines and Isoquinolones
  作者：Qianqian Zhen、Lepeng Chen、Linjun Qi、Kun Hu、Yinlin Shao、Renhao Li、Jiuxi Chen

  DOI：10.1002/asia.201901442

  日期：2020.1.2

  example of the nickel-catalyzed tandem addition/cyclization of 2-(cyanomethyl)benzonitriles with arylboronic acids in 2-MeTHF has been developed, which provides the facile synthesis of aminoisoquinolines with good functional group tolerance under mild conditions. This chemistry has also been successfully applied to the synthesis of isoquinolones by the tandem reaction of methyl 2-(cyanomethyl)benzoates

  已经开发了在2-MeTHF中镍催化的芳基硼酸串联（2-（氰基甲基）苄腈串联/加成环的第一个例子），该化合物在温和条件下可轻松合成具有良好官能团耐受性的氨基异喹啉。通过2-（氰基甲基）苯甲酸甲酯与芳基硼酸的串联反应，该化学方法也已成功地用于异喹诺酮的合成。使用生物基和绿色溶剂2-MeTHF作为反应介质使合成过程在环境方面无害。这种化学的合成效用还通过生物活性分子的合成来表明。
• A simple access to N-(un)substituted isoquinolin-1(2H)-ones: unusual formation of regioisomeric isoquinolin-1(4H)-ones
  作者：R. Gangadhara Chary、G. Dhananjaya、K. Vara Prasad、S. Vaishaly、Y. S. S. Ganesh、Balakrishna Dulla、K. Shiva Kumar、Manojit Pal

  DOI：10.1039/c4cc01580k

  日期：——

  afforded the first practical, one-pot and general approach towards synthesis of N-(un)substituted isoquinolin-1(2H)-ones. Both the catalyst and the solvent used are recyclable. The use of the Cu reagent in excess led to the unusual formation of regioisomeric and uncommon isoquinolin-1(4H)-ones.

  配体/添加剂/无Pd的铜介导的偶联/环化策略为合成N-（未）取代的异喹啉-1（2H）-酮提供了第一个实用的，一锅通用的通用方法。所用的催化剂和溶剂都是可回收的。过量使用铜试剂会导致区域异构和不常见的异喹啉-1（4H）-1的异常形成。
• Tandem Addition/Cyclization for Access to Isoquinolines and Isoquinolones via Catalytic Carbopalladation of Nitriles
  作者：Linjun Qi、Kun Hu、Shuling Yu、Jianghe Zhu、Tianxing Cheng、Xiaodong Wang、Jiuxi Chen、Huayue Wu

  DOI：10.1021/acs.orglett.6b03499

  日期：2017.1.6

  sequential nucleophilic addition followed by an intramolecular cyclization of functionalized nitriles with arylboronic acids has been achieved, providing an efficient synthetic pathway to access structurally diverse isoquinolines and isoquinolones. This methodology has also been successfully applied to the total synthesis of the topoisomerase I inhibitor CWJ-a-5 (free base).

  已经实现了钯催化的连续亲核加成，然后用芳基硼酸进行分子内官能化腈分子内环化的第一个例子，从而提供了一种有效的合成途径，以获取结构多样的异喹啉和异喹啉酮。该方法也已成功应用于拓扑异构酶I抑制剂CWJ-a-5（游离碱）的全合成。
• Synthesis of Functionalized Isoquinolin-1(2<i>H</i>)-ones by Copper-Catalyzed α-Arylation of Ketones with 2-Halobenzamides
  作者：Yan Shi、Xuebin Zhu、Haibin Mao、Hongwen Hu、Chengjian Zhu、Yixiang Cheng

  DOI：10.1002/chem.201301621

  日期：2013.8.26

  Copper is key: A concise route to isoquinolin‐1(2H)‐ones from simple and readily available starting materials is provided by an efficient copper‐catalyzed annulation of ketones with 2‐halobenzamides. The method is applicable to a wide range of ketones containing different functional groups furnishing the products in moderate to excellent yields.

  铜是关键：有效的铜催化酮与2-卤代苯甲酰胺的环合反应可提供从简单易得的起始原料到异喹啉-1（2 H）-one的简捷途径。该方法适用于范围广泛的含有不同官能团的酮，从而以中等至极好的收率提供了产品。