2-methyl-4-phenylisoquinolin-1(2H)-one | 108960-88-9

• 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
• 英文名称: 2-methyl-4-phenylisoquinolin-1(2H)-one
• 英文别名: 2-methyl-4-phenyl-1(2H)-isoquinolone；2-methyl-4-phenylisoquinolin-1-one；2-methyl-4-phenyl-2H-isoquinolin-1-one；2-Methyl-4-phenyl-2H-isochinolin-1-on；2-Methyl-4-phenyl-isocarbostyryl；2-methyl-4-phenyl-1(2H)-isoquinolinone
• CAS: 108960-88-9
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: WWSYAOSOUAEOIE-UHFFFAOYSA-N

物化性质

• 熔点：
  184.5-186.5 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  400.3±45.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-4-phenylisoquinolin-1(2H)-one 在 silver hexafluoroantimonate 、 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 乙酸-D1 作用下， 反应 0.17h， 以98%的产率得到2-methyl-4-phenylisoquinolin-1(2H)-one-8-d
  参考文献：
  名称：

  Catalyst Controlled Divergent C4/C8 Site-Selective C–H Arylation of Isoquinolones

  摘要：

  The catalyst-controlled C4/C8 site-selective C-H arylation of isoquinolones using aryliodonium salts as the coupling partners was developed. The C4-selective arylation was successfully achieved via an electrophilic palladation pathway. A completely different selectivity pattern was observed using an Ir(III) catalytic system, which resulted in C-C bond formation exclusively at the C8 position. The isoquinolone scaffold can be conveniently equipped with various aryl substituents at either the C4 or C8 position.

  DOI：

  10.1021/acs.orglett.5b01840
• 作为产物：
  描述：

  N-甲基苯甲酰胺 在 palladium on activated charcoal 正丁基锂 、 氯化亚砜 、 硫酸 、 氢气 作用下， 反应 18.34h， 生成 2-methyl-4-phenylisoquinolin-1(2H)-one
  参考文献：
  名称：

  有效合成4-芳基-1,2,3,4-四氢异喹啉

  摘要：

  描述了由3-芳基邻苯二甲酸酯合成N-甲基-1,2,3,4-四氢异喹啉的一般方法。

  DOI：

  10.1039/c39870000191

文献信息

• Direct Pd(II)-Catalyzed Site-Selective C5-Arylation of 2-Pyridone Using Aryl Iodides
  作者：Saurabh Maity、Debapratim Das、Souradip Sarkar、Rajarshi Samanta

  DOI：10.1021/acs.orglett.8b02112

  日期：2018.9.7

  transformation was highly regioselective and accomplished with a wide scope and functional group tolerance. Silver nitrate played a crucial role in this direct site-selective arylation. The method was extended to synthesize biologically active molecules.

  开发了一种简单的Pd（II）催化的一般策略，用于使用容易获得的芳基碘化物对2-吡啶酮核心进行C5选择性芳基化。该转化是高度区域选择性的，并且在宽范围和功能基团耐受性下完成。硝酸银在这种直接的位点选择性芳基化中起着至关重要的作用。该方法扩展到合成生物活性分子。
• BROMODOMAIN INHIBITORS
  申请人：Quanticel Pharmaceuticals

  公开号：US20150111885A1

  公开（公告）日：2015-04-23

  The present invention relates to substituted heterocyclic derivative compounds, compositions comprising said compounds, and the use of said compounds and compositions for epigenetic regulation by inhibition of bromodomain-mediated recognition of acetyl lysine regions of proteins, such as histones. Said compositions and methods are useful for the treatment of cancer and neoplastic disease.

  本发明涉及替代杂环衍生物化合物，包括所述化合物的组合物，以及通过抑制溴结构域介导的蛋白质乙酰赖氨酸区域的识别来进行表观遗传调控的所述化合物和组合物的用途。所述组合物和方法对于癌症和肿瘤性疾病的治疗是有用的。
• Synthesis of 4-Iodoisoquinolin-1(2<i>H</i>)-ones by a Dirhodium(II)-Catalyzed 1,4-Bisfunctionalization of Isoquinolinium Iodide Salts
  作者：Zaixiang Fang、Yi Wang、Yuanhua Wang

  DOI：10.1021/acs.orglett.8b03614

  日期：2019.1.18

  An efficient Rh2(II,II)-catalyzed reaction has been developed under mild conditions. This synthetic method proceeds through iodination/oxidation of readily available isoquinolinium iodide salts under aerobic conditions with good to excellent yields. 4-Iodoisoquinolin-1(2H)-ones are important building blocks for biologically and medicinally important compounds. The developed methodology was applied

  在温和条件下已开发出有效的Rh 2（II，II）催化反应。该合成方法是通过在好氧条件下容易获得的碘化异喹啉鎓碘化物盐的碘化/氧化来进行的，具有良好或优异的收率。4-碘异喹啉-1（2 H）-1是生物学上和医学上重要的化合物的重要组成部分。所开发的方法应用于革兰氏合成CRTH2拮抗剂CRA-680的关键中间体。
• A new synthetic route to 2-alkyl-4-aryl-1(2H)-isoquinolones and 2-alkyl-4-aryl-1,2,3,4-tetrahydroisoquinolines
  作者：Axel Couture、Eric Deniau、Pierre Grandclaudon、Patrice Woisel

  DOI：10.1016/0040-4020(96)00092-0

  日期：1996.3

  4-Aryl and heteroaryl-1(2H)-isoquinolones have been prepared by base promoted cyclization of phosphorylated o-aroyl and heteroaroyl benzamides. Subsequent reduction of the carbonyl and styryl functions of the annulated products has given rise to 4-aryl-1,2,3,4-tetrahydroisoquinolines.

  已经通过磷酸化的邻芳基和杂芳基苯甲酰胺的碱促进的环化反应制备了4-芳基和杂芳基-1（2 H）-异喹诺酮。环化产物的羰基和苯乙烯基官能团的随后还原产生了4-芳基-1,2,3,4-四氢异喹啉。
• [EN] BROMODOMAIN INHIBITOR<br/>[FR] INHIBITEUR DE BROMODOMAINES
  申请人：CELGENE QUANTICEL RES INC

  公开号：WO2016172618A1

  公开（公告）日：2016-10-27

  Described herein is the bromodomain inhibitor 4-[2-(cyclopropylmethoxy)-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one, including crystalline forms, amorphous forms, solvates, and hydrates thereof, as well as pharmaceutical compositions that include this bromodomain inhibitor. In some embodiments the pharmaceutical composition comprises 4 [2 (cyclopropylmethoxy)-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one that has been processed by micronization or spray dried dispersion. In some embodiments, the pharmaceutical composition further comprises at least one polymer. In some embodiments, the pharmaceutical compositions comprises a solid polymer matrix comprising 4-[2-(cyclopropylmethoxy)-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one and at least one polymer. Pharmaceutical compositions comprising 4-[2-(cyclopropylmethoxy)-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one are useful for the treatment of cancer or neoplastic disease.

  本文介绍了溴结构域抑制剂4-[2-(环丙基甲氧基)-5-甲基磺酰基苯基]-2-甲基异喹啉-1-酮，包括晶体形式、非晶形式、溶剂化物和水合物，以及包含该溴结构域抑制剂的药物组合物。在某些实施例中，药物组合物包括经微粉化或喷雾干燥分散处理的4-[2-(环丙基甲氧基)-5-甲基磺酰基苯基]-2-甲基异喹啉-1-酮。在某些实施例中，药物组合物进一步包括至少一种聚合物。在某些实施例中，药物组合物包括固态聚合物基质，其中包括4-[2-(环丙基甲氧基)-5-甲基磺酰基苯基]-2-甲基异喹啉-1-酮和至少一种聚合物。包含4-[2-(环丙基甲氧基)-5-甲基磺酰基苯基]-2-甲基异喹啉-1-酮的药物组合物对于治疗癌症或肿瘤性疾病有用。