2-(mercaptomethyl)-1-methylimidazole | 92615-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(mercaptomethyl)-1-methylimidazole
• 英文别名: (1-methyl-1H-imidazol-2-yl)methanethiol；(1-methylimidazol-2-yl)methanethiol
• CAS: 92615-06-0
• 化学式: C₅H₈N₂S
• 分子量: 128.198
• InChiKey: UVWSKIZHAMYEAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(mercaptomethyl)-1-methylimidazole 在 lithium hydroxide monohydrate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 32.0h， 生成 2-methyl-4-((((1-methyl-1H-imidazol-2-yl)methyl)thio)methyl)benzoic acid
  参考文献：
  名称：

  WO2024121779A1

  摘要：

  公开号：
• 作为产物：
  描述：

  acetylthiourea 以 乙醇 、 乙腈 为溶剂， 生成 2-(mercaptomethyl)-1-methylimidazole
  参考文献：
  名称：

  Carbapenem antibiotics

  摘要：

  公开了新型的碳青霉烯衍生物，其特征在于2-取代基的公式为##STR1##，其中A代表C.sub.1-C.sub.6的直链或支链亚烷基；R.sup.5代表可选地取代的脂肪族、环脂肪族、环脂肪族-脂肪族、芳香族、芳脂肪族、杂芳族、杂芳脂肪族、杂环基或杂环基-脂肪族基团；而##STR2##代表一个含氮的芳香杂环，通过亚烷基A与环上的碳原子相连，并通过取代基R.sup.5进行季铵化。这样的衍生物作为强效的抗菌剂是有用的。

  公开号：

  US04644061A1
• 作为试剂：
  描述：

  N-甲酰吗啉 在 potassium chloride 、 重水 、 2-(mercaptomethyl)-1-methylimidazole 作用下， 生成 吗啉 、 甲酸
  参考文献：
  名称：

  Catalysis of Amide Hydrolysis and Formation under Neutral Conditions by a Zwitterionic Imidazolium Thiolate

  摘要：

  As a simple model for the hydrolysis of peptides mediated by the cysteine proteases, 2-(mercaptomethyl)1-methylimidazole (1) was used to catalyze the hydrolysis of four nonactivated amides, namely, formamide, dimethylformamide, N-formylmorpholine, and formanilide (3a-d), at 98 degrees C, pD 7.6-8.0, mu = 1.0 (KCl). Progress of the hydrolysis reactions was followed by H-1 NMR, and the kinetics as a function of added II] were used to determine the second-order catalytic rate constants (k(cat)). A putative intermediate S-formyl thiolester of 1 (4) was not observed to build up during the course of the hydrolysis: the partitioning of authentic 4 between H2O and morpholine and between H2O and aniline was determined (98 degrees C, pD 8.0). The hydrolysis of N-formylmorphline was observed to be catalyzed by added phosphate buffer under the same conditions. When the hydrolysis of a 200 mM D2O solution of N-formylmorpholine was allowed to proceed to completion, an equilibrium position of 33 mM amide, 167 mM HCO2H, and 167 mM morpholine was attained: that same equilibrium position was obtained starting with a solution 200 mM in each of HCO2H and morpholine. The conditional equilibrium constant, K'(eq) = [NFM]/([HCO2H](tot)-[morpholine](tot)), was found to be 1.2 M(-1).

  DOI：

  10.1021/ja00090a015

文献信息

• Optically Active Antifungal Azoles. II. Synthesis and Antifungal Activity of Polysulfide Derivatives of (2R,3R)-2-(2,4-Difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol.
  作者：Akihiro TASAKA、Norikazu TAMURA、Yoshihiro MATSUSHITA、Ryogo HAYASHI、Kenji OKONOGI、Katsumi ITOH

  DOI：10.1248/cpb.41.1043

  日期：——

  In an effort to find potent antifungal agents, a variety of optically active triazole derivatives with a polysulfide structure, 3, 4 and 5, were prepared and evaluated for antifungal activity against Candida albicans in vitro and in vivo. The symmetrical polysulfides 3 (m=2-4) were obtained by an oxidative coupling reaction of (2R, 3R)-2-(2, 4-difluorophenyl)-3-mercapto-1-(1H-1, 2, 4-triazol-1-yl)-2-butanol (1) or by the treatment of its thiocarbonate derivative 8 with potassium tert-butoxide. The unsymmetrical disulfides 5 were synthesized by the reaction of the thiol 1 with Bunte salts 11 or the thiosulfinate 12 or by the reaction of the thiocarbonate 8 with various thiols 13. All of these polysulfides showed potent antifungal activity against candidosis in mice.

  为了寻找有效的抗真菌药物，我们制备并评估了一系列具有多硫化物结构的具有光学活性的三唑衍生物3、4和5，在体外和体内对白色念珠菌的抗真菌活性。通过对（2R, 3R）-2-（2, 4-二氟苯基）-3-巯基-1-（1H-1, 2, 4-三唑-1-基）-2-丁醇（1）的氧化偶联反应或其硫代碳酸酯衍生物8与叔丁醇钾的处理，得到了对称的多硫化物3（m=2-4）。通过对硫醇1与Bunte盐11或硫代亚磺酸盐12的反应，或通过硫代碳酸酯8与各种硫醇13的反应，合成了不对称二硫化物5。所有这些多硫化物都显示出对小鼠念珠菌病有强大的抗真菌活性。
• Attack of zwitterionic ammonium thiolates on a distorted anilide as a model for the acylation of papain by amides. A simple demonstration of a bell-shaped pH/rate profile
  作者：J. W. Keillor、R. S. Brown

  DOI：10.1021/ja00047a004

  日期：1992.10

  A distorted anilide (4) has been shown to be remarkably susceptible to attack by thiolates containing pendant N-H + groups. Thiolates alone are not reactive nor are amines or ammonium ions. Attack of the zwitterionic form produces a thiol ester+which is isolable in the case of N,N-dimethylcysteamine. If the pendant amine is primary, as in the case of cysteamine, the isolable product is the amide formed

  扭曲的苯胺 (4) 已被证明非常容易受到含有悬垂 NH + 基团的硫醇盐的攻击。单独的硫醇盐没有反应性，胺或铵离子也没有反应性。两性离子形式的攻击产生硫羟酸酯+，其在N,N-二甲基半胱胺的情况下是可分离的。如果侧链胺是伯胺，如在半胱胺的情况下，可分离的产物是通过分子内 S 到 N 酰基转移形成的酰胺。2-(巯基甲基)-N-甲基咪唑 (1b) 在 4 上的反应动力学显示出钟形 pH 与 log k 2 曲线，这是由两性离子形式对酰胺的攻击引起的
• Solution Phase Synthesis of Dithymidine Phosphorodithioate Using New S-Protecting Groups in Combination with a Chemoselective Coupling Reagent (PyNOP)
  作者：Jan Kehler、Ask Püschl、Otto Dahl

  DOI：10.1080/07328319708002518

  日期：1997.1

  A method for the synthesis of O-thymidin-3'-yl S-alkyl dithiophosphate monomers 1 with different S-protecting groups has been developed. These for solution phase synthesis of dithymidine phosphorodithioate by a new method. Coupling reactions are fast (15 min.) and the products phosphorothioate contaminations.
• VYAS, DOLATRAI M.;BENIGNI, DANIEL E. A., J. ANTIBIOTICS, 42,(1989) N, C. 1199-1201
  作者：VYAS, DOLATRAI M.、BENIGNI, DANIEL E. A.

  DOI：——

  日期：——
• KIM, CHOUNG UN;MISCO, PETER F.;LUH, BING Y.;HITCHCOCK, MICHAEL J. M., J. ANTIBIOTICS, 40,(1987) N 12, 1707-1710
  作者：KIM, CHOUNG UN、MISCO, PETER F.、LUH, BING Y.、HITCHCOCK, MICHAEL J. M.

  DOI：——

  日期：——