2-[(2-hydroxyeth-1-yl)thio]-4,5-diphenyl-1H-imidazole | 24692-31-7

• 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-[(2-hydroxyeth-1-yl)thio]-4,5-diphenyl-1H-imidazole
• 英文别名: 4,5-Diphenyl-2-<β-hydroxy-aethyl>-mercaptoimidazol；2-(4,5-diphenyl-1H-imidazol-2-ylsulfanyl)-ethanol；2-(4,5-diphenyl-1H-imidazol-2-ylmercapto)-ethanol；2-(4,5-Diphenyl-1H-imidazol-2-ylmercapto)-aethanol；2-[(4,5-diphenyl-1H-imidazol-2-yl)sulfanyl]ethanol
• CAS: 24692-31-7
• 化学式: C₁₇H₁₆N₂OS
• 分子量: 296.393
• InChiKey: OZYPCYKICLAHSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(2-hydroxyeth-1-yl)thio]-4,5-diphenyl-1H-imidazole 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.1h， 以78%的产率得到3,4-diphenyl-6,7-dihydro-imidazo[2,1-b][1,3]thiazole
  参考文献：
  名称：

  Novel Regioselective Hydroxyl-Alkylation of 4,5-Diphenylimidazole-2-Thione and A Competitive Intramolecular Ring Closure of the S-Hydroxyalkyl-Imidazoles to Imidazo[2,1-b]Thiazines and Thiazoles. Role of Catalyst, Microwave Irradiation, and Solid Support

  摘要：

  Under both conventional method (CM) and microwave (MW) irradiation (MWI) conditions, alkylation of 4,5-diphenylimidazole-2-thione (1) with halogeno-alkanols 2 or 5, chloroglycerol 11 and 2,3-O-isopropylidene-1-O-(p-tolylsulfonyl)-glycerol (8) in presence of sodium ethoxide or sodium acetate in alcohol afforded regioselectively the corresponding S-alkylated analogues 3, 6, 9, and 12; they also were obtained using MW in absence and presence of bentonite as solid support with no change in regioselectivity. In the presence of potassium carbonate in DMF, the bisalkylated analogues 4, 7, 10, and 13 were obtained except in case of compound 13 where it was accompanied with the imidazothiazine 14. A convenient approach for imidazo-[2,1-b] thiazines and thiazoles 14 - 16 could be achieved by intramolecular dehydrative ring closure of the S-hydroxyalkylated imidazoles 3, 6, and 12 using potassium carbonate in DMF under both conventional and microwave methods. Isopropylidenation of 12 and 13 and deprotection of 9 and 10 also were investigated.

  DOI：

  10.1080/15257770701426179
• 作为产物：
  描述：

  2-溴乙醇 、 4,5-二苯基-2-咪唑硫醇 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.02h， 以89%的产率得到2-[(2-hydroxyeth-1-yl)thio]-4,5-diphenyl-1H-imidazole
  参考文献：
  名称：

  Novel Regioselective Hydroxyl-Alkylation of 4,5-Diphenylimidazole-2-Thione and A Competitive Intramolecular Ring Closure of the S-Hydroxyalkyl-Imidazoles to Imidazo[2,1-b]Thiazines and Thiazoles. Role of Catalyst, Microwave Irradiation, and Solid Support

  摘要：

  Under both conventional method (CM) and microwave (MW) irradiation (MWI) conditions, alkylation of 4,5-diphenylimidazole-2-thione (1) with halogeno-alkanols 2 or 5, chloroglycerol 11 and 2,3-O-isopropylidene-1-O-(p-tolylsulfonyl)-glycerol (8) in presence of sodium ethoxide or sodium acetate in alcohol afforded regioselectively the corresponding S-alkylated analogues 3, 6, 9, and 12; they also were obtained using MW in absence and presence of bentonite as solid support with no change in regioselectivity. In the presence of potassium carbonate in DMF, the bisalkylated analogues 4, 7, 10, and 13 were obtained except in case of compound 13 where it was accompanied with the imidazothiazine 14. A convenient approach for imidazo-[2,1-b] thiazines and thiazoles 14 - 16 could be achieved by intramolecular dehydrative ring closure of the S-hydroxyalkylated imidazoles 3, 6, and 12 using potassium carbonate in DMF under both conventional and microwave methods. Isopropylidenation of 12 and 13 and deprotection of 9 and 10 also were investigated.

  DOI：

  10.1080/15257770701426179

文献信息

• Synthesis of 2,3-dihydro-and 2,3,5,6-tetrahydro derivatives of imidazo(2,1-B)-thiazole
  作者：I. A. Mazur、P. M. Kochergin、V. I. Fomenko

  DOI：10.1007/bf00832994

  日期：1969.8
• EP0519996A1
  申请人：——

  公开号：EP0519996A1

  公开（公告）日：1992-12-30
• [EN] IMIDAZOLES
  申请人：RHONE-POULENC RORER LIMITED

  公开号：WO1991013876A1

  公开（公告）日：1991-09-19

  (EN) Imidazole derivates of general formula (II) in which R1 is hydrogen or one or more substituents, k is 0, 1 or 2, Q is a straight or branched alkylene group and Z is hydrogen or a substituent group and pharmaceutically acceptable salts thereof possess useful pharmacological properties as inhibitors of acyl coenzyme-A: cholesterol-o-acyl transferase and as inhibitors of the binding of thromboxane TXA2 to its receptors, and are useful in therapy.(FR) On décrit des dérivés d'imidazoles de formule générale (II) dans laquelle R1 est hydrogène ou un ou plusieurs substituants, k représente 0, 1 ou 2, Q est un groupe d'alkylène droit ou ramifié et z est hydrogène ou un groupe de substitution, ainsi que leurs sels pharmaceutiquement acceptables. Lesdits dérivés possèdent des propriétés pharmacologiques utiles en tant qu'inhibiteurs de la coenzyme-A d'acyle: cholestérol-0-acyle transférase et en tant qu'inhibiteurs de la liaison de thromboxane TXA2 à ses récepteurs, et ils sont également utiles dans les traitements.