6-chloro-2,4-dimethyl-4-(2,2,2-trifluoroethyl)isoquinoline-1,3(2H,4H)-dione | 1513867-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-chloro-2,4-dimethyl-4-(2,2,2-trifluoroethyl)isoquinoline-1,3(2H,4H)-dione
• 英文别名: 2,4-Dimethyl-4-(2,2,2-trifluoroethyl)-6-chloroisoquinoline-1,3(2H,4H)-dione；6-chloro-2,4-dimethyl-4-(2,2,2-trifluoroethyl)isoquinoline-1,3-dione
• CAS: 1513867-15-6
• 化学式: C₁₃H₁₁ClF₃NO₂
• 分子量: 305.684
• InChiKey: OCBYYXZLDUPXNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-chloro-N-methacryloyl-N-methylbenzamide 、 (三氟甲基)三甲基硅烷 在 potassium fluoride 、 碘苯二乙酸 、 sodium carbonate 作用下， 以 乙酸乙酯 为溶剂， 以70%的产率得到6-chloro-2,4-dimethyl-4-(2,2,2-trifluoroethyl)isoquinoline-1,3(2H,4H)-dione
  参考文献：
  名称：

  Metal-Free Direct Intramolecular Carbotrifluoromethylation of Alkenes to Functionalized Trifluoromethyl Azaheterocycles

  摘要：

  The first example of a metal-free direct carbotrifluoromethylation of alkenes using inexpensive TMSCF3 as the CF3 source is described. The methodology not only exhibits high chemoselectivity for this transformation but also expands the substrate scope that is difficult to access by known transition-metal-catalyzed methods.

  DOI：

  10.1021/ol403391v

文献信息

• Electrochemical trifluoromethylation/cyclization for the synthesis of isoquinoline-1,3-diones and oxindoles
  作者：Yuanqiang Guo、Ruiguo Wang、Hongjian Song、Yuxiu Liu、Qingmin Wang

  DOI：10.1039/d1cc03389a

  日期：——

  reduction to generate trifluoromethyl radicals. The trifluoromethylation reagent (IMDN-SO2CF3) used in this strategy is inexpensive and easy to obtain, and the reaction can be conducted efficiently without the addition of additional redox reagents. Using this strategy, we achieved electrochemical trifluoromethylation/cyclization for the synthesis of isoquinoline-1,3-diones and oxindoles. This protocol

  在这里，我们描述了一种电化学阴极还原生成三氟甲基自由基的协议。该策略中使用的三氟甲基化试剂（IMDN-SO 2 CF 3）价格低廉且易于获得，并且无需添加额外的氧化还原试剂即可有效地进行反应。使用这种策略，我们实现了用于合成异喹啉-1,3-二酮和羟吲哚的电化学三氟甲基化/环化。该协议具有良好的官能团耐受性和广泛的底物范围。
• Visible-light induced di- and trifluoromethylation of N-benzamides with fluorinated sulfones for the synthesis of CF₂H/CF₃-containing isoquinolinediones
  作者：Guanglong Zou、Xuelin Wang

  DOI：10.1039/c7ob02226c

  日期：——

  visible light induced direct difluoromethylation of N-methacryloyl benzamides by using difluoromethyl sulfone was developed. In addition, photoredox-catalyzed trifluoromethylation of N-methacryloyl benzamides with trifluoromethyl sulfone via a similar radical process was also achieved. This method allows for an efficient and practical synthesis of a variety of CF2H/CF3-containing isoquinoline-1,3(2H,4H)-diones

  利用二氟甲基砜开发了一种普通的可见光诱导的N-甲基丙烯酰基苯甲酰胺直接二氟甲基化方法。另外，还通过类似的自由基过程，实现了光氧化还原催化的N-甲基丙烯酰基苯甲酰胺与三氟甲基砜的三氟甲基化。该方法允许以中等至良好的产率高效且实用地合成各种含CF 2 H / CF 3的异喹啉-1,3（2H，4H）-二酮。该反应具有温和的反应条件，操作简便性和广泛的底物范围。
• Mn-Mediated Electrochemical Trifluoromethylation/C(sp²)–H Functionalization Cascade for the Synthesis of Azaheterocycles
  作者：Zhenxing Zhang、Lei Zhang、Yang Cao、Feng Li、Guangcan Bai、Guoquan Liu、Yang Yang、Fanyang Mo

  DOI：10.1021/acs.orglett.8b04010

  日期：2019.2.1

  A general electrohemical strategy for the combined trifluoromethylation/C(sp(2))-H functionalization using Langlois' reagent as the CF3 source under oxidant-free conditions was developed. Using Mn salts as the redox mediator, this method provides an efficient and sustainable I means to access a variety of functionalized heterocycles bearing a CF3 moiety. Detailed mechanistic studies are consistent with the formation of CF3-bound high oxidation state Mn species, suggesting a transition-metal-mediated CF3 transfer mechanism for this trifluoromethylation/C(sp(2))-H functionalization process.
• Metal-Free Direct Intramolecular Carbotrifluoromethylation of Alkenes to Functionalized Trifluoromethyl Azaheterocycles
  作者：Lei Li、Min Deng、Sheng-Cai Zheng、Ya-Ping Xiong、Bin Tan、Xin-Yuan Liu

  DOI：10.1021/ol403391v

  日期：2014.1.17

  The first example of a metal-free direct carbotrifluoromethylation of alkenes using inexpensive TMSCF3 as the CF3 source is described. The methodology not only exhibits high chemoselectivity for this transformation but also expands the substrate scope that is difficult to access by known transition-metal-catalyzed methods.