sodium 4-pyridyl sulfonate | 14156-63-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: sodium 4-pyridyl sulfonate
• 英文别名: pyridine-4-sulfonic acid ; sodium-salt；Pyridin-4-sulfonsaeure; Natrium-Salz；3-pyridinesulfonic acid, sodium salt；Sodium pyridine-4-sulfonate；sodium;pyridine-4-sulfonate
• CAS: 14156-63-9
• 化学式: C₅H₄NO₃S*Na
• 分子量: 181.147
• InChiKey: TXPCWCLOELZHBM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.01
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sodium 4-pyridyl sulfonate 在 fluorine 作用下， 以 various solvent(s) 为溶剂， 以74%的产率得到N-fluoropyridinium-4-sulfonate
  参考文献：
  名称：

  Highly Selective Fluorinating Agents: a Counteranion-Bound N-Fluoropyridinium Salt System

  摘要：

  A series of alkyl- or (trifluoromethyl)-substituted N-fluoropyridinium-2-sulfonates 2a-h, differing in fluorinating power, were synthesized, and assessment was made of the effectiveness of each selective fluorinating agent. N-Fluoropyridinium-3- and -4-sulfonates 3 and 4 were also synthesized. Power-variables 2a-h were found to be highly selective fluorinating agents for a wide range of nucleophilic substrates such as activated aromatics, enol trialkylsilyl and alkyl ethers, active methylene compounds, activated olefins, and sulfides. Thus, phenol, naphthol, phenylurethane, and the trimethylsilyl ether of phenol were exclusively or highly selectively fluorinated at the o-position with 2f-h. Conjugated enol trialkylsilyl ethers of a steroid were regioselectively fluorinated at the 6-position with moderately powerful 2b-e. This regioselectivity increased with the bulkiness of the silyl part, and with the most bulky triisopropylsilyl group exclusive B-fluorination was achieved. Preferential beta-stereoselective fluorination at the 6-position was observed. N-Fluoropyridinium-2-sulfonates were activated with an acid. This acid-catalyzed fluorination led to the preferential p-fluorination of anisole. The present results can be explained based on the capacity of the 2-sulfonate anion to interact with the hydroxy group of phenol or naphthol, NH group of phenylurethane, silicon atoms of silyl ethers, or protons of acids.

  DOI：

  10.1021/jo00125a049
• 作为产物：
  描述：

  N-nitropyridinium nitrate 在 sodium hydrogensulfite 作用下， 反应 1.0h， 以9%的产率得到sodium 4-pyridyl sulfonate
  参考文献：
  名称：

  C-Nitration of pyridine by the kyodai-nitration modified by the Bakke procedure. A simple route to 3-nitropyridine and mechanistic aspect of its formation

  摘要：

  N-Nitropyridinium nitrate was generated in situ from pyridine, nitrogen dioxide and ozone in an inert organic solvent and subsequently treated with aqueous sodium hydrogen sulfite to afford 3-nitropyridine in good yield, together with sodium pyridine-4-sulfonate as a water-soluble by-product. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01229-x

文献信息

• Electrostatic Interactions Accelerating Water Oxidation Catalysis via Intercatalyst O–O Coupling
  作者：Jiajia Yi、Shaoqi Zhan、Lin Chen、Qiang Tian、Ning Wang、Jun Li、Wenhua Xu、Biaobiao Zhang、Mårten S. G. Ahlquist

  DOI：10.1021/jacs.0c07103

  日期：2021.2.17