1-(2,3-isopropylidene-2,3-dihydroxyprop-1-yl)-2-[(2,3-O-isopropylidene-2,3-dihydroxyprop-1-yl)thio]-4,5-diphenylimidazole | 1027627-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2,3-isopropylidene-2,3-dihydroxyprop-1-yl)-2-[(2,3-O-isopropylidene-2,3-dihydroxyprop-1-yl)thio]-4,5-diphenylimidazole
• CAS: 1027627-21-9
• 化学式: C₂₇H₃₂N₂O₄S
• 分子量: 480.628
• InChiKey: FLPVLERTUMJGEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54.74
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-(2,3-isopropylidene-2,3-dihydroxyprop-1-yl)-2-[(2,3-O-isopropylidene-2,3-dihydroxyprop-1-yl)thio]-4,5-diphenylimidazole 在 水 、 溶剂黄146 作用下， 反应 2.0h， 生成 1-(2,3-dihydroxyprop-1-yl)-2-[(2,3-dihydroxyprop-1-yl)thio]-4,5-diphenylimidazole
  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：

  2,2-二甲基-1,3-二氧环戊基-4-甲醇对甲基苯磺酸酯 、 4,5-二苯基-2-咪唑硫醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以75%的产率得到1-(2,3-isopropylidene-2,3-dihydroxyprop-1-yl)-2-[(2,3-O-isopropylidene-2,3-dihydroxyprop-1-yl)thio]-4,5-diphenylimidazole
  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