sodium p-aminobenzensulfinate

• 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: sodium p-aminobenzensulfinate
• 英文别名: sodium 4-aminobenzenesulfinic acid；Sodium;4-sulfinatoaniline
• 化学式: C₆H₆NO₂S*Na
• 分子量: 179.175
• InChiKey: CSMYGPGJXOXTMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.06
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  硝基苯 、 sodium p-aminobenzensulfinate 在 trans-N,N'-dimethyl-1,2-cyclohexyldiamine 、 sodium hydrogen sulfate 、 iron(II) chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以84%的产率得到磺胺苯
  参考文献：
  名称：

  Iron-Catalyzed N-Arylsulfonamide Formation through Directly Using Nitroarenes as Nitrogen Sources

  摘要：

  One-step, catalytic synthesis of N-arylsulfonamides via the construction of N-S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N-S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.

  DOI：

  10.1021/acs.joc.5b00130

文献信息

• 光催化条件下合成砜类化合物的方法
  申请人：河南大学

  公开号：CN112574077B

  公开（公告）日：2022-02-22

  本发明属于化合物制备技术领域，具体涉及一种光催化条件下合成砜类化合物的方法。以芳肼和亚磺酸盐为原料，在碱和溶剂作用下，经可见光光照，在空气或者氧气条件下反应生成砜类化合物。本发明方法以芳肼作为芳基化试剂，以多酸盐为催化剂或者有机光敏剂为催化剂，在室温条件下经可见光照射，便可实现与亚磺酸盐偶联高效合成砜类化合物。该方法具有较好的底物普适性和相对温和的反应条件，不仅是目前报道从简单底物出发经偶联合成砜类化合物的一种替代，而且还拓宽了多酸盐在光催化领域的新应用。
• Combinatorial synthesis and biological evaluations of (<i>E</i>)-β-trifluoromethyl vinylsulfones as antitumor agents
  作者：Haosha Tang、Yunyan Kuang、Julan Zeng、Xiaofang Li、Wei Zhou、Yuan Lu

  DOI：10.1039/c9ra06368d

  日期：——

  Combinatorial synthesis of (E)-β-trifluoromethyl vinylsulfones is accomplished through a reaction of alkynes, Togni reagent, and sodium benzenesulfinates in DMSO under metal-free conditions at room temperature. These compounds are evaluated in several assays against different tumor cells. Some hits are identified against ES-2, HO-8910, and K562.

  ( E )-β-三氟甲基乙烯基砜的组合合成是通过炔烃、Togni 试剂和苯亚磺酸钠在 DMSO 中在无金属条件下在室温下反应完成的。这些化合物在针对不同肿瘤细胞的多种测定中进行了评估。一些命中结果是针对 ES-2、HO-8910 和 K562 的。
• 8-amino-6-(arylsulphonyl)-5-nitroquinolines: novel nonpeptide neuropeptide Y1 receptor antagonists
  作者：Jon Wright、Gary Bolton、Mark Creswell、Dennis Downing、Lynn Georgic、Thomas Heffner、John Hodges、Robert MacKenzie、Lawrence Wise

  DOI：10.1016/0960-894x(96)00319-8

  日期：1996.8

  A novel series of 8-amino-6-(arylsulphonyl)-5-nitroquinoline neuropeptide Y1 (NPY) receptor antagonists is reported. The 8-amino and 5-nitro groups were important for NPY1 binding affinity as changes caused large drops in potency. The 6-arylsulphonyl group was necessary; however, substitution on the phenyl was tolerated. The 2-isopropyl analog 21 was a moderately potent, highly selective NPY1 receptor antagonist. Copyright (C) 1996 Elsevier Science Ltd
• Desideri, N.; Manna, F.; Stein, M. L., Farmaco, Edizione Scientifica, 1980, vol. 35, # 11, p. 902 - 912
  作者：Desideri, N.、Manna, F.、Stein, M. L.、Arena, F.、Luraschi, E.、Cifra, E.

  DOI：——

  日期：——
• Iron-Catalyzed <i>N</i>-Arylsulfonamide Formation through Directly Using Nitroarenes as Nitrogen Sources
  作者：Weixi Zhang、Junyao Xie、Bin Rao、Meiming Luo

  DOI：10.1021/acs.joc.5b00130

  日期：2015.4.3

  One-step, catalytic synthesis of N-arylsulfonamides via the construction of N-S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N-S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.