2-(4-(trifluoromethyl)phenyl)quinoxaline | 1287795-34-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(4-(trifluoromethyl)phenyl)quinoxaline
• 英文别名: 2-[4-(Trifluoromethyl)phenyl]quinoxaline
• CAS: 1287795-34-9
• 化学式: C₁₅H₉F₃N₂
• 分子量: 274.245
• InChiKey: MMVTWTJTIPOGMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-(trifluoromethyl)phenyl)quinoxaline 在 菲啶 、 diiodo(p-cymene)ruthenium(II) dimer 、 C₃₄H₃₃O₄P 、 氢气 作用下， 以 苯 为溶剂， 20.0 ℃ 、689.49 kPa 条件下， 反应 48.0h， 以93%的产率得到(R)-2-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroquinoxaline
  参考文献：
  名称：

  Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation

  摘要：

  A new and easily regenerable NAD(P)H model 9,10-dihydrophenanthridine (DHPD) has been designed for biomimetic asymmetric hydrogenation of imines and aromatic compounds. This reaction features the use of hydrogen gas as terminal reductant for the regeneration of the DHPD under the mild condition. Therefore, the substrate scope is not limited in benzoxazinones; the biomimetic asymmetric hydrogenation of benzoxazines, quinoxafines, and quinolines also gives excellent activities and enantioselectivities. Meanwhile, an unexpected reversal of enantioselectivity was observed between the reactions promoted by the different NAD(P)H models, which is ascribed to the different hydride transfer pathway.

  DOI：

  10.1021/ja211684v
• 作为产物：
  描述：

  4-三氟甲基苯甲酰氯 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 29.0h， 生成 2-(4-(trifluoromethyl)phenyl)quinoxaline
  参考文献：
  名称：

  铱催化的磺化ulf盐类胡萝卜素插入物在水中合成喹喔啉和β-酮基硫醚

  摘要：

  这项工作证明了通过关键的N–H插入，利用sulf基亚砜作为安全的卡宾来源制备喹喔啉的有效和绿色合成策略。该方法还适用于在温和且经济的条件下合成β-酮硫醚的S–H插入物。该策略避免了重氮化合物的安全性问题和有机溶剂的使用，从而满足了可持续化学的要求。

  DOI：

  10.1002/ejoc.202000716

文献信息

• One-Pot Construction of Indolo[2,3-<i>b</i>]quinoxalines through Ruthenium-Catalyzed <i>Ortho</i> C–H Bond Functionalization of 2-Arylquinoxalines with Sulfonyl Azides
  作者：Sudip Laru、Suvam Bhattacharjee、Sumit Ghosh、Alakananda Hajra

  DOI：10.1021/acs.orglett.1c02837

  日期：2021.10.1

  N-substituted indolo[2,3-b]quinoxalines has been developed through a Ru(II)-catalyzed ortho C–H functionalization of 2-arylquinoxalines with sulfonyl azides and further oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in one pot. This double C–N bond formation strategy provides a new efficient route for the preparation of a series of biologically relevant 6H-indolo[2,3-b]quinoxaline derivatives in

  N-取代的吲哚并[2,3- b ]喹喔啉的合成是通过Ru(II)催化的2-芳基喹喔啉与磺酰叠氮化物的邻位C-H官能化并用2,3-二氯-5进一步氧化而开发的， 6-二氰基-1,4-苯醌一锅。这种双C-N键形成策略为制备一系列生物相关的6 H-吲哚[2,3- b ]喹喔啉衍生物提供了一条新的有效途径，产率高达94%，表明底物适用范围广泛。初步的机理研究表明，连续的 C-N 键形成是通过第一步中五元钌环中间体的形成和第二步中自由基机制的形成进行的。
• One-step approach for the synthesis of functionalized quinoxalines mediated by T3P®–DMSO or T3P® via a tandem oxidation–condensation or condensation reaction
  作者：Kachigere B. Harsha、Kanchugarkoppal S. Rangappa

  DOI：10.1039/c6ra03078e

  日期：——

  An easy and efficient propylphosphonic anhydride (T3P®)–DMSO or T3P® mediated oxidation–condensation or condensation reaction for the synthesis of quinoxalines derived from the interaction of different arrays of condensing partners with ortho-phenylene diamines (o-PDs) under simple and mild reaction conditions in one step has been reported for the first time.

  一种简单有效的丙基膦酸酐（T3P®）-DMSO或T3P®介导的氧化-缩合或缩合反应，用于合成喹喔啉，该喹喔啉是在简单和简单的条件下衍生自不同阵列的缩合配偶与邻苯二胺（o -PDs）相互作用的产物。首次报道温和的反应条件。
• [EN] INHIBITORS OF HIF PROLYL HYDROXYLASE<br/>[FR] INHIBITEURS DE LA HIF PROLYL-HYDROXYLASE
  申请人：MERCK SHARP & DOHME

  公开号：WO2016049099A1

  公开（公告）日：2016-03-31

  The present invention concerns compounds of formula I or pharmaceutically acceptable salts thereof, which inhibit HIF prolyl hydroxylase, their use for enhancing endogenous production of erythropoietin, and for treating conditions associated with reduced endogenous production of erythropoietin such as anemia and like conditions, as well as pharmaceutical compositions comprising such a compound and a pharmaceutical carrier.

  本发明涉及式I的化合物或其药用盐，其抑制HIF脯氨酸羟化酶，用于增强内源性促红细胞生成素的产生，并用于治疗与内源性促红细胞生成素减少相关的疾病，如贫血和类似疾病，以及包含该化合物和药用载体的药物组合物。
• Electrochemical Arylation of Electron‐Deficient Arenes through Reductive Activation
  作者：Pan Wang、Zhenlin Yang、Ziwei Wang、Chenyang Xu、Lei Huang、Shengchun Wang、Heng Zhang、Aiwen Lei

  DOI：10.1002/anie.201909600

  日期：2019.10.28

  An electrochemical method has been developed to achieve arylation of electron-deficient arenes through reductive activation. Various electron-deficient arenes and aryldiazonium tetrafluoroborates are amenable to this transformation within the conditions of an undivided cell, providing the desired products in up to 92 % yield. Instead of preparing diazonium reagents, these reactions can begin from anilines

  已经开发出一种电化学方法以通过还原活化来实现电子不足的芳烃的芳基化。各种电子不足的芳烃和四氟硼酸芳基重氮盐都适合在未分裂的电池条件下进行这种转化，从而以高达92％的收率提供所需的产物。这些反应可以从苯胺开始，而不是制备重氮试剂，并且可以在一个锅中进行。电子顺磁共振研究表明，使用该转变可发生喹喔啉的阴极还原。此外，循环伏安法表明喹喔啉盐和芳基重氮盐都具有相对较低的还原电位，这表明它们可以在反应过程中通过还原而被活化。
• Direct C‐2 arylation of quinoxaline with arylhydrazine salts as arylation reagents
  作者：Xing Wang、Bing Wang、Jing Miao、Yi Chen、Gaofeng Zhu、Jiquan Zhang、Jianta Wang、Haibo Wang、Lei Tang、Cong Wang

  DOI：10.1002/jhet.4465

  日期：2022.7

  A transition metal-free synthesis of 2-arylquinoxaline is achieved by using arylhydrazine salt as an aryl radical arylation reagent and air as an oxidant in the presence of K2CO3. This protocol features metal-free, no additives, mild reaction conditions, environment friendly, and can be used to construct biologically active molecules containing 2-phenylquinoxaline structure.

  在 K 2 CO 3存在下，使用芳基肼盐作为芳基自由基芳基化试剂，空气作为氧化剂，实现了 2-芳基喹喔啉的无过渡金属合成。该方案不含金属、无添加剂、反应条件温和、环境友好，可用于构建含有2-苯基喹喔啉结构的生物活性分子。