1-amino-2-(1-hydroxyethyl)pyrazin-1-ium 2,4,6-trimethylbenzenesulfonate | 1201762-95-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1-amino-2-(1-hydroxyethyl)pyrazin-1-ium 2,4,6-trimethylbenzenesulfonate
• CAS: 1201762-95-9
• 化学式: C₆H₁₀N₃O*C₉H₁₁O₃S
• 分子量: 339.415
• InChiKey: FKUZNYMWHHFDJS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  120.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2,4,6-三甲基苯磺酰羟胺 、 1-(吡嗪-2-基)乙醇 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-amino-2-(1-hydroxyethyl)pyrazin-1-ium 2,4,6-trimethylbenzenesulfonate 、 1-amino-3-(1-hydroxyethyl)pyrazin-1-ium 2,4,6-trimethylbenzenesulfonate
  参考文献：
  名称：

  Regioselectivity in 2-X-pyrazine aminations by O-mesitylenesulfonylhydroxylamine

  摘要：

  The regioselectivity of 2-X-pyrazine aminations by O-mesitylenesulfonylhydroxylamine was studied experimentally and the results are discussed from the viewpoint of electronic and steric factors. DFT calculations are consistent with the reaction proceeding according to an S(N)2 mechanism. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.103

文献信息

• Regioselectivity in the amination of azines: Reaction of pyrazine derivatives with O-mesitylenesulfonylhydroxylamine
  作者：G. I. Borodkin、A. Yu. Vorob’ev、M. M. Shakirov、V. G. Shubin

  DOI：10.1134/s1070428011060108

  日期：2011.6

  Treatment of 2-X-substituted pyrazines [X = H, Me, Et, Pr, i-Pr, t-Bu, MeCH(OH), H2N, AcNH] with O-mesitylenesulfonylhydroxylamine gave the corresponding 2-X- and 3-X-(1-amino)pyrazin-1-ium mesitylenesulfonates. 2-Alkylpyrazines (X = Me, Et, Pr, i-Pr) displayed a correlation between the logarithms of the concentration ratio of 2- and 3-substituted cations and substituent steric constants. Wider series of substituted pyrazines [X = H, Me, Et, Pr, i-Pr, MeCH(OH), H2N, AcNH] conformed to a multiparameter correlation between the logarithms of the concentration ratio of 2- and 3-substituted cations, on the one hand, and substituent constants sigma(I), sigma (R) (o) , and E (s) (o) , on the other. The obtained data on the regioselectivity of amination of pyrazines were interpreted in terms of DFT/PBE/3Z quantum-chemical calculations.