trimethyl-[2-(4-nitro-benzoylmercapto)-ethyl]-ammonium; iodide | 110386-84-0

• 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: trimethyl-[2-(4-nitro-benzoylmercapto)-ethyl]-ammonium; iodide
• 英文别名: Trimethyl-[2-(4-nitro-benzoylmercapto)-aethyl]-ammonium; Jodid；Trimethyl-[2-(4-nitrobenzoyl)sulfanylethyl]azanium;iodide
• CAS: 110386-84-0
• 化学式: C₁₂H₁₇N₂O₃S*I
• 分子量: 396.249
• InChiKey: ZEYHYDUXRAHFKF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.82
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  88.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trimethyl-[2-(4-nitro-benzoylmercapto)-ethyl]-ammonium; iodide 在 水 作用下， 生成 4-nitrobenzoate
  参考文献：
  名称：

  Intramolecular Catalysis of Thiol Ester Hydrolysis by a Tertiary Amine and a Carboxylate

  摘要：

  The syntheses of 4-nitro thiol benzoate esters of ethyl 2-mercaptoacetate, thioglycolic acid, 2-(dimethylamino)ethanethiol, and 2(N,N,N,-trimethylammono)ethanethiol iodide (10-13) have been carried out and their rates of hydrolysis at 50 degrees C studied as a function of pH. Thiol esters 10 and 13 have linear pH-log k(obs) profiles indicative of an exclusive specific base attack of OH-. Thiol esters 11 and 12 exhibit a plateau in their pH/log k(obs) profiles due to the participation of pendant carboxylate and dimethylamino groups, respectively, most probably as intramolecular general bases. At higher pH, specific base catalysis becomes predominant for both 11 and 12. In the plateau region, the hydrolysis of 12 is subject to a solvent deuterium kinetic isotope effect of 2.2, consistent with the operation of a general base role for the pendant dimethylamino group. The hydrolysis of 12 in the presence of Ellman's reagent produces the Ellman's anion at a rate that is identical to that for disappearance of the thioester, consistent with a general base process where the thiolate anion product of hydrolysis is produced in the rate-limiting step.

  DOI：

  10.1021/jo9623954
• 作为产物：
  描述：

  S-[2-(Dimethylamino)ethyl] 4-nitrobenzenecarbothioate 、 碘甲烷 以 乙醚 为溶剂， 以96%的产率得到trimethyl-[2-(4-nitro-benzoylmercapto)-ethyl]-ammonium; iodide
  参考文献：
  名称：

  Intramolecular Catalysis of Thiol Ester Hydrolysis by a Tertiary Amine and a Carboxylate

  摘要：

  The syntheses of 4-nitro thiol benzoate esters of ethyl 2-mercaptoacetate, thioglycolic acid, 2-(dimethylamino)ethanethiol, and 2(N,N,N,-trimethylammono)ethanethiol iodide (10-13) have been carried out and their rates of hydrolysis at 50 degrees C studied as a function of pH. Thiol esters 10 and 13 have linear pH-log k(obs) profiles indicative of an exclusive specific base attack of OH-. Thiol esters 11 and 12 exhibit a plateau in their pH/log k(obs) profiles due to the participation of pendant carboxylate and dimethylamino groups, respectively, most probably as intramolecular general bases. At higher pH, specific base catalysis becomes predominant for both 11 and 12. In the plateau region, the hydrolysis of 12 is subject to a solvent deuterium kinetic isotope effect of 2.2, consistent with the operation of a general base role for the pendant dimethylamino group. The hydrolysis of 12 in the presence of Ellman's reagent produces the Ellman's anion at a rate that is identical to that for disappearance of the thioester, consistent with a general base process where the thiolate anion product of hydrolysis is produced in the rate-limiting step.

  DOI：

  10.1021/jo9623954

文献信息

• Benzoylthiocholine derivatives as substrates for pseudocholinesterase : Synthesis and application.
  作者：MAGOHEI YAMADA、YOJI MARUI、CHOZO HAYASHI、SHOJI TAKEMURA

  DOI：10.1248/cpb.35.1491

  日期：——

  Substituted benzoylthiocholines were synthesized and their application as reagents for clinical measurement of pseudocholinesterase was investigated. Among 21 compounds, 2, 3-dimethoxybenzoylthiocholine (19b) was found to be an excellent substrate for the measurement of the enzyme. The procedure was simple and self-hydrolysis of the substrate at the optimum pH of the enzyme was minimal.

  合成的取代苯甲酰硫代胆碱化合物，并研究了它们作为临床测量假胆碱酯酶试剂的应用。在21种化合物中，2,3-二甲氧基苯甲酰硫代胆碱（19b）被发现是测量该酶的优秀底物。该方法简便，且底物在酶的最适pH下自水解程度最小。
• Thioesters of Choline and β-Methylcholine and their Physiological Activity. Onium Compounds. XIX
  作者：R. R. Renshaw、P. F. Dreisbach、M. Ziff、D. Green

  DOI：10.1021/ja01275a015

  日期：1938.8