1,3-diethyl-4,5-dimethyl-1H-imidazole-2(3H)-thione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 1,3-diethyl-4,5-dimethyl-1H-imidazole-2(3H)-thione
• 英文别名: 1,3-diethyl-4,5-dimethylimidazole-2(3H)-thione；1,3-Diethyl-4,5-dimethylimidazole-2-thione
• 化学式: C₉H₁₆N₂S
• 分子量: 184.305
• InChiKey: JHHSUMSRHXBZSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-diethyl-4,5-dimethyl-1H-imidazole-2(3H)-thione 在 氢化钾 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以96%的产率得到1,3-diethyl-4,5-dimethylimidazol-2-ylidene
  参考文献：
  名称：

  Synthesis of Imidazol-2-ylidenes by Reduction of Imidazole-2(3H)-thiones

  摘要：

  报道了对标题化合物的改进合成方法。N,N-二烷基硫脲1与3-羟基-2-丁酮反应生成咪唑-2(3H)-硫酮2，后者在沸腾的四氢呋喃中与钾反应，以优异的产率得到咪唑-2-亚基3。

  DOI：

  10.1055/s-1993-25902
• 作为产物：
  描述：

  3-羟基-2-丁酮 、 1,3-二乙基硫脲 以 various solvent(s) 为溶剂， 反应 12.0h， 以61%的产率得到1,3-diethyl-4,5-dimethyl-1H-imidazole-2(3H)-thione
  参考文献：
  名称：

  Synthesis of Imidazol-2-ylidenes by Reduction of Imidazole-2(3H)-thiones

  摘要：

  报道了对标题化合物的改进合成方法。N,N-二烷基硫脲1与3-羟基-2-丁酮反应生成咪唑-2(3H)-硫酮2，后者在沸腾的四氢呋喃中与钾反应，以优异的产率得到咪唑-2-亚基3。

  DOI：

  10.1055/s-1993-25902

文献信息

• Synthesis of New Cationic Cp*Ir N-Heterocyclic Carbene Complexes and Their High Catalytic Activities in the Oppenauer-Type Oxidation of Primary and Secondary Alcohols
  作者：Fumihiro Hanasaka、Ken-ichi Fujita、Ryohei Yamaguchi

  DOI：10.1021/om0503545

  日期：2005.7.1

  Several new cationic Cp*Ir N-heterocyclic complexes have been synthesized and their catalytic activities in the Oppenauer-type oxidation have been investigated in order to improve the catalytic activity of [Cp*IrCl(μ-Cl)]2. The reactions of [Cp*IrCl(μ-Cl)]2 (1) with N-heterocyclic carbene ligands afforded Cp*Ir(L)Cl2 (3a−d; L = N-heterocyclic carbene ligands). The cationic complexes [Cp*Ir(L)(MeCN)2]2+

  为了提高[Cp * IrCl（μ-Cl）] 2的催化活性，已经合成了几种新型的阳离子Cp * Ir N-杂环配合物，并研究了它们在Oppenauer型氧化中的催化活性。[Cp * IrCl（μ-Cl）] 2（1）与N-杂环卡宾配体的反应得到Cp * Ir（L）Cl 2（3a - d； L = N-杂环卡宾配体）。阳离子配合物[Cp * Ir（L）（MeCN）2 ] 2+（5a - d）通过用2当量的AgOTf处理3a - d然后添加CH 3来获得CN。配合物3a - d和5a - d的结构通过X射线晶体学研究确定。络合物5a（L = 1,3,4,5-四甲基咪唑-2-亚烷基）在温和条件下非常选择性地催化伯醇和仲醇的Oppenauer型氧化。在使用5a作为催化剂的1-苯基乙醇和环戊醇的氧化中，周转数分别达到3200和6640。这些结果表明，就我们所知，阳离子卡宾配合物5a由于其高催化活性和对伯
• Low-Coordinate Magnesium Sulfide and Selenide Complexes
  作者：Stuart Burnett、Rochelle Ferns、David B. Cordes、Alexandra M. Z. Slawin、Tanja van Mourik、Andreas Stasch

  DOI：10.1021/acs.inorgchem.3c02132

  日期：2023.10.9

  1-adamantylazide (AdN3) to give [(iPrDipNacNac)Mg}2(μ-SN3Ad)] 7 and can form various simple donor adducts in solution, of which [(iPrDipNacNac)Mg(OAd)}2(μ-S)] 8a (OAd = 2-adamantanone) was structurally characterized. The nature of the ionic Mg–E–Mg unit is described by solution and solid-state studies of the complexes and by DFT computational investigations.

  [( iPrDip NacNac)Mg} 2 ] 1 ( iPrDip nacnac = HC(iPrCNDip) 2 ) 与 Ph 3 P=O 在 100 °C 下反应得到次膦酸盐络合物 [( iPrDip NacNac)Mg(OPPh 3 )(OPPh 2）] 3。1与 Ph 3 P=E (E = S, Se)的反应在室温下快速进行，形成低配位硫族化物配合物 [( iPrDip NacNac)Mg} 2 (μ-S)] 4和 [( iPrDip NacNac)分别为Mg} 2 (μ-Se)] 5。类似地，R NHC=S ((MeCNR) 2 C=S，其中 R = Me、Et 或i Pr) 与1的反应得到硫化镁复合物的 NHC 加合物，[( iPrDip NacNac)Mg( R NHC)}( μ-S)Mg( iPrDip NacNac)}] 6，其也可以通过将适当的R NHC
• Imidazolium-based warheads strongly influence activity of water-soluble peptidic transglutaminase inhibitors
  作者：Eduard Badarau、Alexandre Mongeot、Russell Collighan、Dan Rathbone、Martin Griffin

  DOI：10.1016/j.ejmech.2013.05.018

  日期：2013.8

  New peptidic water-soluble inhibitors are reported. In addition to the carboxylate moiety, a new polar warhead was explored. Depending on the size of its substituents, the newly appended imidazolium scaffold designed to enhance the hydrophilic character of the inhibitors could induce a good inhibition for tissue transglutaminase (TG2) and blood coagulation factor XIIIa (EXIIIa). Correlated with the narrow tunnel that hosts the target catalytic cysteine residue, the various modulations suggest a bent conformation of the ligands as the binding pattern mode. Analogues in the dialkylsulfonium series were also tested and showed specificity for TG2 over FXIIIa. (c) 2013 Elsevier Masson SAS. All rights reserved.
• A Systematic Investigation of Factors Influencing the Decarboxylation of Imidazolium Carboxylates
  作者：Bret R. Van Ausdall、Jeremy L. Glass、Kelly M. Wiggins、Atta M. Aarif、Janis Louie

  DOI：10.1021/jo901791k

  日期：2009.10.16

  A series of 1,3-disubstituted-2-imidazolium carboxylates, an adduct of CO2 and N-heterocyclic carbenes, were synthesized and characterized using single crystal X-ray, thermogravimetric, IR, and NMR analysis. The TGA analysis of the NHC-CO2's shows that as steric bulk on the N-substituent increases, the ability of the NHC-CO2 to decarboxylate increases. The comparison of NHC-CO2's with and without methyls at the 4,5-position indicate that extra electron density in the imidazolium ring enhances the stability of an NHC-CO2 thereby making it less prone to decarboxylation. Single crystal X-ray analysis shows that the torsional angle of the carboxylate group and the C-CO2 bond length with respect to the imidazolium ring is dependent on the steric bulk of the N-substituent. Rotamers in the unit cell of a single crystal of I'BuPrCO2 (2f) indicate that the C-CO2 bond length increases as the N-substituents rotate toward the carboxylate moiety, which suggests that rotation of the N-substituents through the plane of the C-CO2 bond may be involved in the bond breaking event to release CO2.
• A Convenient One-Pot Three Component Approach to Synthesis of Highly Substituted Iminothiazolines
  作者：Manouchehr Mamaghani、Heshmat Allah Samimi、Khalil Tabatabaeian

  DOI：10.3987/com-08-11453

  日期：——