1-(S)-α-methylbenzyl-2-mercaptoimidazole | 928331-18-4

• 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-(S)-α-methylbenzyl-2-mercaptoimidazole
• 英文别名: 3-[(1S)-1-phenylethyl]-1H-imidazole-2-thione
• CAS: 928331-18-4
• 化学式: C₁₁H₁₂N₂S
• 分子量: 204.296
• InChiKey: IYFFDOAOHDAFLX-VIFPVBQESA-N

物化性质

• 沸点：
  309.2±35.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(S)-α-methylbenzyl-2-mercaptoimidazole 在 镍 作用下， 以 甲醇 、 水 为溶剂， 反应 0.08h， 生成 1-[(1S)-1-苯基乙基]咪唑
  参考文献：
  名称：

  Chiral Azole Derivatives. 2. Synthesis of Enantiomerically Pure 1-Alkylimidazoles

  摘要：

  4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 7 (entries 1-7 in Table 1) under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 8, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 10 in good overall yield and high enantiomeric excess. In contrast, when applied to benzyl and benthydryl alcohols (entries 8-15), this sequence afforded the final compounds in good overall yield, but as racemic mixtures. The 1-(1-phenylalkyl)imidazole derivative (S)-(+)-24 was, however, prepared in enantiopure form starting from the corresponding (S)-(-)-alpha-methylbenzylamine (21) using the Marckwald procedure, which entailed the alkylation of 21 with bromoacetaldehyde dimethyl acetal, followed by the construction of the imidazole ring through reaction with potassium thiocyanate and final Ra-Ni desulfuration. Following the same procedure, (S)-(+)-10c was also synthesized, proving the stereochemical outcome of the Mitsunobu reaction.

  DOI：

  10.1021/jo00112a023
• 作为产物：
  描述：

  (S)-(-)-(1-phenylethylamino)acetaldehyde dimethyl acetal 在 盐酸 、 potassium thioacyanate 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以84%的产率得到1-(S)-α-methylbenzyl-2-mercaptoimidazole
  参考文献：
  名称：

  Chiral Azole Derivatives. 2. Synthesis of Enantiomerically Pure 1-Alkylimidazoles

  摘要：

  4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 7 (entries 1-7 in Table 1) under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 8, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 10 in good overall yield and high enantiomeric excess. In contrast, when applied to benzyl and benthydryl alcohols (entries 8-15), this sequence afforded the final compounds in good overall yield, but as racemic mixtures. The 1-(1-phenylalkyl)imidazole derivative (S)-(+)-24 was, however, prepared in enantiopure form starting from the corresponding (S)-(-)-alpha-methylbenzylamine (21) using the Marckwald procedure, which entailed the alkylation of 21 with bromoacetaldehyde dimethyl acetal, followed by the construction of the imidazole ring through reaction with potassium thiocyanate and final Ra-Ni desulfuration. Following the same procedure, (S)-(+)-10c was also synthesized, proving the stereochemical outcome of the Mitsunobu reaction.

  DOI：

  10.1021/jo00112a023

文献信息

• Tripodal borate ligands from tris(dimethylamino)borane: the first synthesis of a chiral tris(methimazolyl)borate ligand, and the crystal structure of a single diastereomer pseudo-C₃-symmetric Ru(<scp>ii</scp>) complex
  作者：Philip J. Bailey、Chiara McCormack、Simon Parsons、Felix Rudolphi、Alejandro Sanchez Perucha、Peter Wood

  DOI：10.1039/b611331a

  日期：——

  The activation of tris(dimethylamino)borane towards reaction with a chiral methimazole by N-methylimidazole has been used to prepare the first example of a chiral tris(methimazolyl)borate ligand. Coordination of this neutral ligand to Ru(II) has been achieved by reaction with [(p-cymene)RuCl2]2 to provide a single diastereomer complex in which the chirality of the methimazolyl substituents dictate

  这 激活 的 三（二甲基氨基）硼烷 与手性甲巯咪唑反应 N-甲基咪唑 已用于制备手性三（甲基咪唑基）硼酸酯的第一个实例 配体。这种中立的协调配体通过与[（p- Cymene）RuCl 2 ] 2反应获得对Ru（II）的对映体，以提供单个非对映异构体配合物，其中甲硫唑基取代基的手性决定了由环戊二烯基形成的双环[3.3.3]笼的手性。配体对金属的配合。手性三（甲基咪唑基）硼酸酯的替代方法配体 通过将取代基探索了将手性基团引入硼原子的过程 N-甲基咪唑 在上述反应中通过手性 恶唑啉 作为简单反应中的活化碱 甲硝唑。然而，尽管B（NMe 2）3被活化以与甲硝唑 通过这些 恶唑啉，通过配位的甲him唑硫磺会发生分子内恶唑啉开环，并阻止这些化合物的成功合成 配体。
• Chiral Azole Derivatives. 2. Synthesis of Enantiomerically Pure 1-Alkylimidazoles
  作者：Federico Corelli、Vincenzo Summa、Alessandra Brogi、Edith Monteagudo、Maurizio Botta

  DOI：10.1021/jo00112a023

  日期：1995.4

  4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 7 (entries 1-7 in Table 1) under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 8, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 10 in good overall yield and high enantiomeric excess. In contrast, when applied to benzyl and benthydryl alcohols (entries 8-15), this sequence afforded the final compounds in good overall yield, but as racemic mixtures. The 1-(1-phenylalkyl)imidazole derivative (S)-(+)-24 was, however, prepared in enantiopure form starting from the corresponding (S)-(-)-alpha-methylbenzylamine (21) using the Marckwald procedure, which entailed the alkylation of 21 with bromoacetaldehyde dimethyl acetal, followed by the construction of the imidazole ring through reaction with potassium thiocyanate and final Ra-Ni desulfuration. Following the same procedure, (S)-(+)-10c was also synthesized, proving the stereochemical outcome of the Mitsunobu reaction.