2,3,4,5,6-pentafluoro-N-(quinolin-8-yl)benzenesulfonamide

• 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: 2,3,4,5,6-pentafluoro-N-(quinolin-8-yl)benzenesulfonamide
• 英文别名: N-(quinolin-8-yl)pentafluorobenzenesulfonamide；2,3,4,5,6-pentafluoro-N-quinolin-8-ylbenzenesulfonamide
• 化学式: C₁₅H₇F₅N₂O₂S
• 分子量: 374.291
• InChiKey: FEKLYMOWHJNRJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲醇 、 四溴化碳 、 2,3,4,5,6-pentafluoro-N-(quinolin-8-yl)benzenesulfonamide 在 tris(bipyridine)ruthenium(II) dichloride hexahydrate 、 potassium carbonate 作用下， 反应 24.0h， 以59%的产率得到methyl 8-(perfluorophenylsulfonamido)quinoline-5-carboxylate
  参考文献：
  名称：

  Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway

  摘要：

  An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ^•CBr₃ radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.

  DOI：

  10.1021/acs.joc.9b00942
• 作为产物：
  描述：

  8-硝基喹啉 在 甲烷 、 一水合肼 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 2,3,4,5,6-pentafluoro-N-(quinolin-8-yl)benzenesulfonamide
  参考文献：
  名称：

  Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway

  摘要：

  An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ^•CBr₃ radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.

  DOI：

  10.1021/acs.joc.9b00942

文献信息

• Non‐emissive Ru ^II Polypyridyl Complexes as Efficient and Selective Photosensitizers for the Photooxidation of Benzylamines
  作者：Cristina Yagüe、Igor Echevarría、Mónica Vaquero、Jairo Fidalgo、Arancha Carbayo、Félix A. Jalón、João C. Lima、Artur J. Moro、Blanca R. Manzano、Gustavo Espino

  DOI：10.1002/chem.202001460

  日期：2020.9.21

  non‐emissive behavior has been related to the low electrochemical energy gaps and rationalized on the basis of theoretical calculations (DFT analysis) that predict low S0←T1 energy values. Moreover, the RuII complexes, despite being non‐emissive, display excellent activities in the selective photocatalytic transformation of benzylamines into the corresponding imines. The presence of an electron‐withdrawing

  制备了五种新的带有N-（芳基磺酰基）-8-氨基喹啉酸酯配体的Ru II聚吡啶基配合物及其双环金属化的Ir III同源物中的三个，并将其用作光催化剂（PC），用于苄胺与O 2的光氧化。尤其是，新的Ru II络合物没有光致发光，而是有效地收集可见光，并且在蓝光照射下在溶液中非常稳定。它们的非发射行为与较低的电化学能隙有关，并根据预测低S 0 ←T 1能量值的理论计算（DFT分析）进行了合理化。而且，汝II配合物尽管不发散，但在苄胺向相应的亚胺的选择性光催化转化中表现出出色的活性。N-（芳基磺酰基）-8-酰氨基喹啉酸酯配体的芳环上存在一个吸电子基团（-CF3），可提高相应光催化剂的光催化活性。此外，所有实验证据，包括瞬态吸收光谱法测量均表明，单重态氧是实际的氧化剂。Ir III类似物的光敏性更高，因此光敏剂（PS）的效率也较低。
• US6528187B1
  申请人：——

  公开号：US6528187B1

  公开（公告）日：2003-03-04
• Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway
  作者：Chiranjit Sen、Tapan Sahoo、Harshvardhan Singh、Eringathodi Suresh、Subhash Chandra Ghosh

  DOI：10.1021/acs.joc.9b00942

  日期：2019.8.16

  An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ^•CBr₃ radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.