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
• 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：——
• Synthesis of Imidazol-2-ylidenes by Reduction of Imidazole-2(3<i>H</i>)-thiones
  作者：Norbert Kuhn、Thomas Kratz

  DOI：10.1055/s-1993-25902

  日期：——

  An improved synthesis of the title compounds is reported. Reaction of the N,N-dialkylthioureas 1 with 3-hydroxy-2-butanone gives the imidazole-2(3H)-thiones 2 which on treatment with potassium in boiling tetrahydrofuran give the imidazol-2-ylidenes 3 in excellent yields.

  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。