2-cyclopropylquinolin-4(1H)-one | 461666-04-6

• 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: 2-cyclopropylquinolin-4(1H)-one
• 英文别名: 2-Cyclopropyl-1,4-dihydroquinolin-4-one；2-cyclopropyl-1H-quinolin-4-one
• CAS: 461666-04-6
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: RNOILIZGNHABIB-UHFFFAOYSA-N

物化性质

• 沸点：
  375.1±30.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-cyclopropylquinolin-4(1H)-one 在 四(三苯基膦)钯 sodium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-[4-(2-cyclopropyl-quinolin-4-ylmethyl)-benzoylamino]-tetrahydro-pyran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  A new 4-(2-methylquinolin-4-ylmethyl)phenyl P1′ group for the β-amino hydroxamic acid derived TACE inhibitors

  摘要：

  A new P1' group for TACE inhibitors was identified by eliminating the oxygen atom in the linker of the original 4-(2methylquinolin-4-ylmethoxy)phenyl P1' group. Incorporation of this 4-(2-methylquinolin-4-ylmethyl)phenyl group onto different beta-aminohydroxamic acid cores provided compound 18, which demonstrated potent porcine TACE (p-TACE) and human whole blood activity, excellent PK properties, and good selectivity against a variety of MMPs. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.041
• 作为产物：
  描述：

  3-cyclopropyl-3-phenylimino-propionic acid methyl ester 以 二苯醚 为溶剂， 生成 2-cyclopropylquinolin-4(1H)-one
  参考文献：
  名称：

  A new 4-(2-methylquinolin-4-ylmethyl)phenyl P1′ group for the β-amino hydroxamic acid derived TACE inhibitors

  摘要：

  A new P1' group for TACE inhibitors was identified by eliminating the oxygen atom in the linker of the original 4-(2methylquinolin-4-ylmethoxy)phenyl P1' group. Incorporation of this 4-(2-methylquinolin-4-ylmethyl)phenyl group onto different beta-aminohydroxamic acid cores provided compound 18, which demonstrated potent porcine TACE (p-TACE) and human whole blood activity, excellent PK properties, and good selectivity against a variety of MMPs. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.041

文献信息

• Access to 2-Alkyl/Aryl-4-(1<i>H</i>)-Quinolones via Orthogonal “NH₃” Insertion into <i>o</i>-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F
  作者：Shweta Singh、Sharanya Nerella、Srihari Pabbaraja、Goverdhan Mehta

  DOI：10.1021/acs.orglett.0c00172

  日期：2020.2.21

  An efficient one-pot synthesis of 4-(1H)-quinolones through an orthogonal engagement of diverse o-haloaryl ynones with ammonia in the presence of Cu(I), involving tandem Michael addition and ArCsp2-N coupling, is presented. The substrate scope of this convenient protocol, wherein ammonium carbonate acts as both an in situ ammonia source and a base toward diverse 2-substituted 4-(1H)-quinolones, has

  提出了一种有效的一锅法合成4-（1H）-喹诺酮的方法，该方法是在Cu（I）存在下，通过串联的迈克尔加成反应和ArCsp2-N偶联作用，使多种邻卤代芳基炔酮与氨进行正交结合。已绘制出此便捷方案的底物范围，其中碳酸铵既可作为原位氨源，又可作为多种2-取代的4-（1H）-喹诺酮类的碱，并且其功效已通过生物活性天然产物的简明全合成进行了验证假单胞菌（IV，VII，VIII和XII），砾石，gravolinine和waltherioneF。
• 异吲哚啉类化合物、其制备方法、药物组合物及用途
  申请人：中国科学院上海药物研究所

  公开号：CN110963994B

  公开（公告）日：2022-02-08

  本发明涉及如通式(I)所表示的多取代异吲哚啉类化合物，其制备方法、药物组合物及应用。具体的，本发明提供的多取代异吲哚啉类化合物作为一类结构新颖的CRL4CRBNE3泛素连接酶调节剂具有更强的抗肿瘤活性和抗肿瘤谱，可以用于制备治疗与CRL4CRBNE3泛素连接酶相关的疾病的药物。
• Supported palladium-catalyzed carbonylative cyclization of 2-bromonitrobenzenes and alkynes to access quinolin-4(1H)-ones
  作者：Jian-Shu Wang、Chenyu Li、Jun Ying、Tiefeng Xu、Wangyang Lu、Chuan-Ying Li、Xiao-Feng Wu

  DOI：10.1016/j.jcat.2022.02.026

  日期：2022.4

  palladium supported on graphitic carbon nitride (Pd/g-CN) catalyzed carbonylative cyclization of 2-bromonitrobenzenes and alkynes has been developed for the expedite construction of quinolin-4(1)-one scaffolds. By using a low loading heterogeneous palladium catalyst, Mo(CO) as both the CO surrogate and the reductant, and nitroarenes as the nitrogen source, the reaction proceeded well to give a variety

  开发了一种负载于石墨氮化碳 (Pd/g-CN) 上的钯催化 2-溴硝基苯和炔烃的羰基环化，用于加快构建 quinolin-4(1)-one 支架。通过使用低负载量的多相钯催化剂、Mo(CO)作为CO替代物和还原剂、硝基芳烃作为氮源，反应进展顺利，得到了多种从良好到优异的喹啉-4(1)-酮。产量。
• Generation of ArS- and ArSe-Substituted 4-Quinolone Derivatives Using Sodium Iodide As an Inducer
  作者：Prasanjit Ghosh、Aritra Kumar Nandi、Gautam Chhetri、Sajal Das

  DOI：10.1021/acs.joc.8b01426

  日期：2018.10.19

  An operationally simple sodium iodide-mediated C–S and C–Se bond formation protocol involving substituted 4-quinolone and thiols/diselenide to generate different ArS/ArSe-substituted 4-quinolone derivatives in excellent yields was developed. The versatility of this methodology has been successfully demonstrated by extension of the suitable reaction conditions to both substrates having different substituents

  开发了一种操作简单的碘化钠介导的C S和C Se键形成方案，该方案涉及取代的4-喹诺酮和硫醇/二硒化物，以优异的产率生成不同的ArS / ArSe取代的4-喹诺酮衍生物。通过将合适的反应条件扩展至具有不同取代基的两种底物，已成功证明了该方法的多功能性。这种区域选择性的C–H键活化方法可直接进入结构多样的3-磺基化/硒基化的4-喹诺酮衍生物。而且，这种新方法无需过渡金属催化剂和对4-喹诺酮衍生物的必要的NH保护就可以进行。
• Creation of thio and selenocyanate derivatives of 4-quinolone <i>via</i> regioselective C–H bond functionalization under ambient conditions
  作者：Prasanjit Ghosh、Gautam Chhetri、Aritra Kumar Nandi、Sagar Sarkar、Tilak Saha、Sajal Das

  DOI：10.1039/c9nj01922g

  日期：——

  An operationally simple C–SCN and C–SeCN bond formation technique to generate different SCN/SeCN substituted 4-quinolone derivatives using NH₄SCN/KSeCN in excellent yields was developed.

  开发了一种操作简单的C-SCN和C-SeCN键形成技术，利用NH₄SCN/KSeCN生成不同SCN/SeCN取代的4-喹啉酮衍生物，收率极高。