(2-hydroxy-ethyl)-dimethyl sulfonium ; bromide | 63580-72-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-hydroxy-ethyl)-dimethyl sulfonium ; bromide
• 英文别名: (2-Hydroxy-aethyl)-dimethyl-sulfonium; Bromid；(2-Hydroxyethyl)(dimethyl)sulfanium bromide；2-hydroxyethyl(dimethyl)sulfanium;bromide
• CAS: 63580-72-3
• 化学式: Br*C₄H₁₁OS
• 分子量: 187.101
• InChiKey: LWIHIIAVUJLFKL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.14
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-hydroxy-ethyl)-dimethyl sulfonium ; bromide 、 溶剂黄146 在 sodium chloride 作用下， 生成 2-(dimethylsulfonio)methyl acetate bromide
  参考文献：
  名称：

  Effects of volume and surface property in hydrolysis by acetylcholinesterase. The trimethyl site

  摘要：

  beta-Substituted ethyl acetates, XCH2CH2OCOCH3, have been prepared, and their hydrolysis by acetylcholinesterase has been studied. Log of enzymic reactivity, normalized for intrinsic reactivity in hydrolysis by hydroxide, log (kcat/Km)n, rises linearly with increasing refraction volume, MR (or RD25), for substrates with beta-X = H, Cl, Br, CH3CH2, (CH3)2CH, (CH3)2S+, (CH3)3N+, and (CH3)3C. Larger substituents may be accommodated, (CH3)3Si and (CH3CH2)3N+, with no further increase in rate. Substrates with beta-substituents CH3S, CH3S(O), (CH3)3N+(OH), and CH3S(O2) are less reactive than consistent with the relation with MR by factors of 5-40, indicating that hydrophobic surface and desolvation of the substrate--enzyme interface may be necessary for maximum reactivity correlated with MR. Values of log (kcat/Km)n for substrates with beta-substituents X = CH3S, Cl, Br, CH3CH2, (CH3)2CH, (CH3)3C, and (CH3)3Si rise linearly with increasing hydrophobicity, pi, but reactivity of substrates with X = (CH3)3N+ and (CH3)2S+ are more reactive than consistent with a relation to pi by factors of 300 and 40 and with X = CH3S(O2), CH3S(O), and (CH3)2N+(OH), by factors of 7-100. Reactivity appears related to (i) volume of the beta-substituent and its fit in its subsite, which is trimethyl rather than anionic, and (ii) the hydrophobicity of its surface.

  DOI：

  10.1021/jm00378a020
• 作为产物：
  描述：

  dimethyl-vinyl sulfonium ; bromide 在 氢氧化钾 作用下， 生成 (2-hydroxy-ethyl)-dimethyl sulfonium ; bromide
  参考文献：
  名称：

  d-Orbital Resonance. II. Comparative Reactivity of Vinyldimethylsulfonium and Vinyltrimethylammonium Ions¹

  摘要：

  DOI：

  10.1021/ja01608a002

文献信息

• d-Orbital Resonance. II. Comparative Reactivity of Vinyldimethylsulfonium and Vinyltrimethylammonium Ions¹
  作者：W. von E. Doering、Kurt C. Schreiber

  DOI：10.1021/ja01608a002

  日期：1955.2.1
• Effects of volume and surface property in hydrolysis by acetylcholinesterase. The trimethyl site
  作者：Saul G. Cohen、Jerome L. Elkind、S. Bano Chishti、Jose L. Giner、Heide Reese

  DOI：10.1021/jm00378a020

  日期：1984.12

  beta-Substituted ethyl acetates, XCH2CH2OCOCH3, have been prepared, and their hydrolysis by acetylcholinesterase has been studied. Log of enzymic reactivity, normalized for intrinsic reactivity in hydrolysis by hydroxide, log (kcat/Km)n, rises linearly with increasing refraction volume, MR (or RD25), for substrates with beta-X = H, Cl, Br, CH3CH2, (CH3)2CH, (CH3)2S+, (CH3)3N+, and (CH3)3C. Larger substituents may be accommodated, (CH3)3Si and (CH3CH2)3N+, with no further increase in rate. Substrates with beta-substituents CH3S, CH3S(O), (CH3)3N+(OH), and CH3S(O2) are less reactive than consistent with the relation with MR by factors of 5-40, indicating that hydrophobic surface and desolvation of the substrate--enzyme interface may be necessary for maximum reactivity correlated with MR. Values of log (kcat/Km)n for substrates with beta-substituents X = CH3S, Cl, Br, CH3CH2, (CH3)2CH, (CH3)3C, and (CH3)3Si rise linearly with increasing hydrophobicity, pi, but reactivity of substrates with X = (CH3)3N+ and (CH3)2S+ are more reactive than consistent with a relation to pi by factors of 300 and 40 and with X = CH3S(O2), CH3S(O), and (CH3)2N+(OH), by factors of 7-100. Reactivity appears related to (i) volume of the beta-substituent and its fit in its subsite, which is trimethyl rather than anionic, and (ii) the hydrophobicity of its surface.