5-fluoro-2-methoxybenzenesulfonamide | 444-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-fluoro-2-methoxybenzenesulfonamide
• 英文别名: 5-fluor-2-methoxybenzolsulfonamid；5-fluoro-2-methoxy-benzenesulfonic acid amide；5-Fluor-2-methoxy-benzolsulfonsaeure-amid
• CAS: 444-54-2
• 化学式: C₇H₈FNO₃S
• 分子量: 205.21
• InChiKey: AZYACHYSKDAONB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-fluoro-2-methoxybenzenesulfonamide 在 盐酸 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.83h， 生成 9-fluoro-3-phenyl-4-oxa-1-thia-2-azaspiro[4.5]deca-2,7,9-trien-6-one 1,1-dioxide
  参考文献：
  名称：

  Electrochemical Dearomative Spirocyclization of N‐Acyl Sulfonamides in a Continuous‐Flow Cell^†

  摘要：

  综述开发高效、可持续的方法获得螺环化合物具有重要意义，因为这些结构广泛存在于医药和农用化学品中。在此，我们公开了一种在连续流动池中对 N-酰基磺酰胺进行电化学脱芳香螺环化的方法。该反应简单高效，无需外加催化剂或支撑电解质，可用于十克级合成。

  DOI：

  10.1002/cjoc.202300673
• 作为产物：
  描述：

  对氟苯甲醚 在 chlorosulphuric acid 、 氯仿 作用下， 生成 5-fluoro-2-methoxybenzenesulfonamide
  参考文献：
  名称：

  Identification of Organic Compounds. III. Chlorosulfonic Acid as a Reagent for the Characterization of Aromatic Ethers^1,2

  摘要：

  DOI：

  10.1021/ja01860a049

文献信息

• [EN] PYRAZOLO-PYRIMIDINES AS INHIBITORS OF BTK<br/>[FR] PYRAZOLO-PYRIMIDINES EN TANT QU'INHIBITEURS DE BTK
  申请人：REDX PHARMA PLC

  公开号：WO2015140566A1

  公开（公告）日：2015-09-24

  This invention relates to novel compounds. The compounds of the invention are tyrosine kinase inhibitors. Specifically, the compounds of the invention are useful as inhibitors of Bruton's tyrosine kinase (BTK). The invention also contemplates the use of the compounds for treating conditions treatable by the inhibition of Bruton's tyrosine kinase, for example cancer, lymphoma, leukemia and immunological diseases.

  这项发明涉及新颖的化合物。该发明的化合物是酪氨酸激酶抑制剂。具体来说，该发明的化合物可用作布鲁顿氏酪氨酸激酶（BTK）的抑制剂。该发明还考虑了利用这些化合物治疗通过抑制布鲁顿氏酪氨酸激酶可治疗的疾病，例如癌症、淋巴瘤、白血病和免疫性疾病。
• Identification of Organic Compounds. III. Chlorosulfonic Acid as a Reagent for the Characterization of Aromatic Ethers^1,2
  作者：Ernest H. Huntress、Frederick H. Carten

  DOI：10.1021/ja01860a049

  日期：1940.3
• Thomas, Philipp; Schlebe, Andrea; Seidel, Andreas, Journal fur praktische Chemie (Leipzig 1954), 1991, vol. 333, # 4, p. 657 - 660
  作者：Thomas, Philipp、Schlebe, Andrea、Seidel, Andreas、Hennig, Horst

  DOI：——

  日期：——
• Design and synthesis of new potassium channel activators derived from the ring opening of diazoxide: Study of their vasodilatory effect, stimulation of elastin synthesis and inhibitory effect on insulin release
  作者：Nafila Bouider、Wassim Fhayli、Zeinab Ghandour、Marjorie Boyer、Kamel Harrouche、Xavier Florence、Bernard Pirotte、Philippe Lebrun、Gilles Faury、Smail Khelili

  DOI：10.1016/j.bmc.2015.02.043

  日期：2015.4

  Benzenesulfonylureas and benzenesulfonylthioureas, as well as benzenecarbonylureas and benzenecarbonylthioureas, were prepared and evaluated as myorelaxants on 30 mM KCl-precontracted rat aortic rings. The most active compounds were further examined as stimulators of elastin synthesis by vascular smooth muscle cells and as inhibitors of insulin release from pancreatic beta-cells. The drugs were also characterized for their effects on glycaemia in rats. Benzenesulfonylureas and benzenesulfonylthioureas did not display any myorelaxant activity on precontracted rat aortic rings. Such an effect could be attributed to their ionization at physiological pH. By contrast, almost all benzenecarbonylureas and benzenecarbonylthioureas displayed a myorelaxant activity, in particular the benzenecarbonylureas with an oxybenzyl group linked to the ortho position of the phenyl ring. The vasodilatory activity of the most active compounds was reduced when measured in the presence of 80 mM KCl or in the presence of 30 mM KCl and 10 mu M glibenclamide. Such results suggested the involvement, at least in part, of K-ATP channels. Preservation of a vasodilatory activity in rat aortic rings without endothelium indicated that the site of action of such molecules was located on the vascular smooth muscle cells and not on the endothelial cells. Some of the most active compounds also stimulated elastin synthesis by vascular smooth muscle cells. Lastly, most of the active vasorelaxant drugs, except 15k and 15t at high concentrations, did not exhibit marked inhibitory effects on the insulin releasing process and on glycaemia, suggesting a relative tissue selectivity of some of these compounds for the vascular smooth muscle. (C) 2015 Elsevier Ltd. All rights reserved.
• Electrochemical Dearomative Spirocyclization of <scp><i>N</i>‐Acyl</scp> Sulfonamides in a <scp>Continuous‐Flow</scp> Cell^†
  作者：Ting Liu、Zhaojiang Shi、Yaofeng Yuan、Yuqi Lin、Ke‐Yin Ye

  DOI：10.1002/cjoc.202300673

  日期：2024.5

  The development of efficient and sustainable methods to obtain spirocyclic compounds is of significance as these structures are widely found in pharmaceuticals and agrochemicals. Herein, we disclose an electrochemical dearomative spirocyclization of N‐acyl sulfonamides in a continuous‐flow cell. The reaction is simple and efficient without external catalysts or supporting electrolytes and could be applied in a decagram‐scale synthesis.

  综述开发高效、可持续的方法获得螺环化合物具有重要意义，因为这些结构广泛存在于医药和农用化学品中。在此，我们公开了一种在连续流动池中对 N-酰基磺酰胺进行电化学脱芳香螺环化的方法。该反应简单高效，无需外加催化剂或支撑电解质，可用于十克级合成。