2-(methoxysulfinyl)benzoic acid methyl ester | 90536-67-7

• 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: 2-(methoxysulfinyl)benzoic acid methyl ester
• 英文别名: 1-Methoxycarbonyl-benzolsulfinsaeure-(2)-methylester；2-Methoxycarbonyl-phenyl-sulfinsaeure-methylester；Benzoic acid, 2-(methoxysulfinyl)-, methyl ester；methyl 2-methoxysulfinylbenzoate
• CAS: 90536-67-7
• 化学式: C₉H₁₀O₄S
• 分子量: 214.242
• InChiKey: PGOPPHRRZMEIDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  环己烷 、 2-(methoxysulfinyl)benzoic acid methyl ester 在 二叔丁基过氧化物 、 碘 、 亚磷酸二乙酯 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以72%的产率得到methyl 2-(cyclohexylthio)benzoate
  参考文献：
  名称：

  在无金属条件下以芳基亚烷基磺酸盐为亚硫基化剂合成硫醚和硫酯

  摘要：

  已经进行了关于环烷烃与芳基亚磺酸烷基酯的偶联的研究。使用碘作为催化剂，通过C- H键活化和亚磺酸盐还原反应，以中等至高收率生产了多种硫醚。另外，还可以通过简单地在CO压力下进行反应来制备各种硫代羧酸酯。值得注意的是，这是首次在交叉偶联转化中使用烷基芳基亚磺酸盐作为亚磺酰基化剂的报道。

  DOI：

  10.1002/asia.201601376
• 作为产物：
  描述：

  硫代水杨酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 2-(methoxysulfinyl)benzoic acid methyl ester
  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

• <b>Organic Disulfides and Related Substances. VI. A One-step Synthesis of Aromatic Sulfinic Esters from Lead Tetraacetate and Aromatic Disulfides or Thiols</b>
  作者：Lamar. Field、Charles B. Hoelzel、J. Michael. Locke

  DOI：10.1021/ja00864a033

  日期：1962.3
• Sulfinate Esters from Methoxymethyl Sulfides
  作者：Young Kwan Ko、Dong Wan Koo、Jeong Soon Kim、Dae-Whang Kim

  DOI：10.1080/00397919508011835

  日期：1995.9

  Several benzene(or phenylmethane) sulfinate esters were synthesized in 53-98% yields from the corresponding methoxymethyl(MOM) sulfides employing NBS as oxidant.
• Synthesis of Thioethers and Thioesters with Alkyl Arylsulfinates as the Sulfenylation Agent under Metal-Free Conditions
  作者：Yahui Li、Fengxiang Zhu、Zechao Wang、Xiao-Feng Wu

  DOI：10.1002/asia.201601376

  日期：2016.12.19

  cycloalkanes with alkyl arylsulfinates has been performed. Using iodine as the catalyst, through C −H bond activation and sulfinates reduction, a wide range of thioethers were produced in moderate to high yields. Additionally, various thiocarboxylic esters can also be produced by simply performing the reaction under CO pressure. Notably, this is the first report in which alkyl arylsulfinates were used as

  已经进行了关于环烷烃与芳基亚磺酸烷基酯的偶联的研究。使用碘作为催化剂，通过C- H键活化和亚磺酸盐还原反应，以中等至高收率生产了多种硫醚。另外，还可以通过简单地在CO压力下进行反应来制备各种硫代羧酸酯。值得注意的是，这是首次在交叉偶联转化中使用烷基芳基亚磺酸盐作为亚磺酰基化剂的报道。
• 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.