2-(methylsulfonyl)ethyl acetate | 92543-10-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: 2-(methylsulfonyl)ethyl acetate
• 英文别名: acetic acid-(2-methanesulfonyl-ethyl ester)；Essigsaeure-(2-methansulfonyl-aethylester)；Acetic acid 2-methanesulfonyl-ethyl ester；2-methylsulfonylethyl acetate
• CAS: 92543-10-7
• 化学式: C₅H₁₀O₄S
• mdl: MFCD25969074
• 分子量: 166.198
• InChiKey: RGCIACOELZRWMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  2-(methylsulfonyl)ethyl acetate 在 aluminum oxide 作用下， 生成 甲基乙烯砜
  参考文献：
  名称：

  Preparation of vinyl sulfones

  摘要：

  公开号：

  US02474808A1
• 作为产物：
  描述：

  2-羟乙基甲砜 、 乙酸酐 在 硫酸 作用下， 反应 1.0h， 以48%的产率得到2-(methylsulfonyl)ethyl acetate
  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

文献信息

• Preparation of vinyl sulfones
  申请人：US RUBBER CO

  公开号：US02474808A1

  公开（公告）日：1949-07-05
• 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.