methyl 2-oxo-phenylethane-1-sulfonate | 131353-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-oxo-phenylethane-1-sulfonate
• 英文别名: methyl benzoylmethanesulfonate；methyl 2-oxo-2-phenylethanesulfonate；Methyl benzoylmethane-sulfonate
• CAS: 131353-62-3
• 化学式: C₉H₁₀O₄S
• 分子量: 214.242
• InChiKey: QLZPVVTXGKLBJB-UHFFFAOYSA-N

物化性质

• 熔点：
  77.5-78.0 °C
• 沸点：
  399.5±25.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-oxo-phenylethane-1-sulfonate 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 3.0h， 以60%的产率得到sodium α-oximinobenzoylmethanesulfonate
  参考文献：
  名称：

  Chemistry of β-oxoalkanesulfonic acids as CH-acids

  摘要：

  Ability of beta-oxoalkanesulfonic acids and their esters to enter into the reactions characteristic for CH-acids (azocoupling, nitrosation, aldol condensation, Michael reaction) was demonstrated. New poly-functional aliphatic sulfonic acids were synthesized as a result of these reactions.

  DOI：

  10.1134/s107036321412007x
• 作为产物：
  描述：

  在 溴 作用下， 反应 2.0h， 生成 methyl 2-oxo-phenylethane-1-sulfonate
  参考文献：
  名称：

  二氧化硫介导的多官能磺酰胺和磺酸酯的一锅，三和四组分合成：二氧化硫烯反应的立体选择性研究

  摘要：

  二氧化硫与环氧硅烷或烯丙基硅烷的烯反应生成甲硅烷基亚磺酸盐，可将其溴化（Br 2或NBS）或氯化（NCS或Cl 2）以生产相应的磺酰卤。它们与伯胺和仲胺或醇反应，分别得到相应的磺酰胺和磺酸酯。将二氧化硫异狄尔斯-阿尔德加成到1-氧基或1,3-二氧基-1,3-二烯上会生成两性离子，该两性离子会加到环氧硅烷或烯丙基硅烷中，生成甲硅烷基亚磺酸盐，可将其原位转化为多官能磺酰胺或磺酸酯。这样可以通过一锅，三和四组分方法快速访问复杂的磺酰胺和磺酸酯库。

  DOI：

  10.1021/jo049047j

文献信息

• Polyfunctional sulfonamides and sulfonates and process for preparing them
  申请人：Ecole Polytechnique Fédérale de Lausanne

  公开号：EP1447397A1

  公开（公告）日：2004-08-18

  The present invention relates to a process for preparing sulfonyl halides comprising the steps of a) reacting an enoxymetal, allylsilane or allylstannane compound, preferably in the presence of a diene, with sulphur dioxide and b) adding a suitable halogen source to the metal sulfinate intermediate of step a). Furthermore, the present invention relates to new sulfonyl chlorides, bromides, and iodides, sulfonamides and sulfonates. In addition, the present invention teaches the use of the new multifunctional sulfonamides and sulfonates for the preparation of a medicament, bacteriocides, fungicides, pesticides, and herbicides as well as the use of sulfonyl chlorides for the preparation of sulfonamides and sulfonates.

  本发明涉及一种制备磺酰卤化物的过程，包括以下步骤：a）将enoxymetal、烯丙基硅烷或烯丙基锡化合物与二氧化硫反应，优选在二烯基存在下进行；b）向步骤a）的金属磺酸盐中加入适当的卤素源。此外，本发明还涉及新的磺酰氯化物、溴化物和碘化物、磺酰胺和磺酸盐。此外，本发明还教授了新的多功能磺酰胺和磺酸盐用于制备药物、杀菌剂、杀真菌剂、杀虫剂和除草剂，以及磺酰氯化物用于制备磺酰胺和磺酸盐的用途。
• Active-site-directed modification of subtilisin
  作者：Ziyang Zhong、Jeffrey A. Bibbs、Wei Yuan、Chi Huey Wong

  DOI：10.1021/ja00006a052

  日期：1991.3

  This paper describes the development of several competitive inhibitors and mechanism-based inactivators of subtilisin BPN'. Various methyl arylalkanesulfonates were prepared and shown to be either competitive inhibitors or selective methylating reagents for the epsilon-2-N of the active-site His. Styrene sulfonyl chloride was shown to be a good covalent inactivator and benzyl N-(N-Boc-L-phenylalanyl)-L-aziridine-2-carboxylate was a strong competitive inhibitor. The second-order rate constant of inactivation and the K(i) of the enzyme reacting with the methylating reagents and other inactivators were determined. The methylated enzyme was purified to homogeneity and the kinetic constants for the enzyme-catalyzed ester and amide hydrolyses were determined. It was established that the methylated enzyme lost most of the amidase activity while the esterase activity was still significant and useful for peptide synthesis via aminolysis. A mechanism involving ring flipping of the active-site imidazole, first proposed for methylchymotrypsin activity, was also proposed to explain methylsubtilisin-catalyzed reactions.
• Efimova; Lipina; Berkova, Russian Journal of Organic Chemistry, 1996, vol. 32, # 10, p. 1424 - 1428
  作者：Efimova、Lipina、Berkova、Pozdnyakov

  DOI：——

  日期：——
• ZHONG, ZIYANG;BIBBS, JEFFREY A.;YUAN, WEI;WONG, CHI-HUEY, J. AMER. CHEM. SOC., 113,(1991) N, C. 2259-2262
  作者：ZHONG, ZIYANG、BIBBS, JEFFREY A.、YUAN, WEI、WONG, CHI-HUEY

  DOI：——

  日期：——
• Sulfur Dioxide Mediated One-Pot, Three- and Four-Component Syntheses of Polyfunctional Sulfonamides and Sulfonic Esters:  Study of the Stereoselectivity of the Ene Reaction of Sulfur Dioxide
  作者：Laure C. Bouchez、Srinivas Reddy Dubbaka、Māris Turks、Pierre Vogel

  DOI：10.1021/jo049047j

  日期：2004.9.1

  The ene reaction of sulfur dioxide with enoxysilanes or with allylsilanes generates silyl sulfinates that can be brominated (Br2 or NBS) or chlorinated (NCS or Cl2) to produce the corresponding sulfonyl halides. They react with primary and secondary amines or alcohols to give the corresponding sulfonamides and sulfonic esters, respectively. The hetero-Diels−Alder addition of sulfur dioxide to 1-oxy-

  二氧化硫与环氧硅烷或烯丙基硅烷的烯反应生成甲硅烷基亚磺酸盐，可将其溴化（Br 2或NBS）或氯化（NCS或Cl 2）以生产相应的磺酰卤。它们与伯胺和仲胺或醇反应，分别得到相应的磺酰胺和磺酸酯。将二氧化硫异狄尔斯-阿尔德加成到1-氧基或1,3-二氧基-1,3-二烯上会生成两性离子，该两性离子会加到环氧硅烷或烯丙基硅烷中，生成甲硅烷基亚磺酸盐，可将其原位转化为多官能磺酰胺或磺酸酯。这样可以通过一锅，三和四组分方法快速访问复杂的磺酰胺和磺酸酯库。