2-pyridinesulfinic acid lithium salt | 874273-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-pyridinesulfinic acid lithium salt
• 英文别名: lithium pyridine-2-sulfinate；lithium;pyridine-2-sulfinate
• CAS: 874273-29-7
• 化学式: C₅H₄NO₂S*Li
• 分子量: 149.099
• InChiKey: XKSDMAVIVGGBIO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.68
• 重原子数：
  10
• 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：
  72.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-pyridinesulfinic acid lithium salt 、 4-溴异喹啉 在 potassium carbonate 、 palladium diacetate 、 三环己基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.25h， 以85%的产率得到4-(pyridin-2-yl)isoquinoline
  参考文献：
  名称：

  连续流动作为使能技术：杂芳族亚磺酸盐的合成作为基准稳定的交叉偶联伙伴。

  摘要：

  描述了一种能够进行连续流动的装置，用于处理不稳定的有机锂中间体和合成多克级的杂芳基亚磺酸盐。先进的连续流工艺可实现杂芳基亚磺酸盐的合成和简单分离，否则，以传统的分批方式很难获得。用这种方法制备的亚磺酸锂盐显示出在钯催化的C（sp 2）-C（sp 2）交叉偶联以访问与医学相关的双-杂芳基基序方面是有效的反应伙伴。

  DOI：

  10.1021/acs.orglett.0c02155
• 作为产物：
  描述：

  2-巯基吡啶 在 甲基锂 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 2-pyridinesulfinic acid lithium salt
  参考文献：
  名称：

  Oxidation of Aromatic Lithium Thiolates into Sulfinate Salts:  An Attractive Entry to Aryl Sulfones Labeled with Carbon-11

  摘要：

  [Graphics]Aromatic C-11-sulfones were synthesized by S alkylation of lithium arenesulfinates, which are readily available from the corresponding thiols by an oxaziridine-mediated oxidation reaction with [C-11]alkyl iodides in THF/H2O (4: 1) at 150 degrees C. The radiosyntheses, including purification by HPLC, were completed in an average of 35 min from the end of the bombardment with 55-76% overall radiochemical yields (decay corrected). The described procedure extends the range of accessible labeling methods.

  DOI：

  10.1021/jo051942v

文献信息

• Efficient Desulfinative Cross-Coupling of Heteroaromatic Sulfinates with Aryl Triflate in Environmentally Friendly Protic Solvents
  作者：Pat Forgione、Daniel Mangel、Cindy Buonomano、Stéphane Sévigny、Gianna Di Censo、Gowsic Thevendran

  DOI：10.3987/com-14-s(k)104

  日期：——

  Aryl-substituted heteroaromatics were synthesized via desulfinative cross-coupling reactions using aryl triflate and heteroaromatic sulfinate coupling partners. This method uses synthetically versatile aryl triflates to access aryl-substituted heteroaromatics in good yields employing aqueous and alcoholic media without the use of base, additives or co-catalysts.
• Continuous Flow as Enabling Technology: Synthesis of Heteroaromatic Sulfinates as Bench Stable Cross-Coupling Partners
  作者：Fabio Lima、Jérôme André、Alexander Marziale、Andreas Greb、Susanne Glowienke、Mark Meisenbach、Berthold Schenkel、Benjamin Martin、Joerg Sedelmeier

  DOI：10.1021/acs.orglett.0c02155

  日期：2020.8.7

  synthesis of heteroaryl sulfinates on a multigram scale is described. The developed continuous flow process allows for the synthesis and simple isolation of heteroaryl sulfinates which are otherwise challenging to access in classical batch mode. The lithium sulfinate salts prepared by this method were shown to be efficient reaction partners in palladium catalyzed C(sp2)–C(sp2) cross-coupling to access medicinally

  描述了一种能够进行连续流动的装置，用于处理不稳定的有机锂中间体和合成多克级的杂芳基亚磺酸盐。先进的连续流工艺可实现杂芳基亚磺酸盐的合成和简单分离，否则，以传统的分批方式很难获得。用这种方法制备的亚磺酸锂盐显示出在钯催化的C（sp 2）-C（sp 2）交叉偶联以访问与医学相关的双-杂芳基基序方面是有效的反应伙伴。
• Oxidation of Aromatic Lithium Thiolates into Sulfinate Salts:  An Attractive Entry to Aryl Sulfones Labeled with Carbon-11
  作者：Claudie Martin、Franck Sandrinelli、Cécile Perrio、Stéphane Perrio、Marie-Claire Lasne

  DOI：10.1021/jo051942v

  日期：2006.1.1

  [Graphics]Aromatic C-11-sulfones were synthesized by S alkylation of lithium arenesulfinates, which are readily available from the corresponding thiols by an oxaziridine-mediated oxidation reaction with [C-11]alkyl iodides in THF/H2O (4: 1) at 150 degrees C. The radiosyntheses, including purification by HPLC, were completed in an average of 35 min from the end of the bombardment with 55-76% overall radiochemical yields (decay corrected). The described procedure extends the range of accessible labeling methods.