6,7-diphenyl-2H,3H,4H-3-hydroxytetrahydroimidazo[2,1-b][1,3]thiazine | 34035-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6,7-diphenyl-2H,3H,4H-3-hydroxytetrahydroimidazo[2,1-b][1,3]thiazine
• 英文别名: 2,3-diphenyl-3-hydroxy-6,7-dihydroimidazo[2,1-b][1,3]thiazine；2,3-diphenyl-6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazin-6-ol；2,3-diphenyl-6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazin-6-ol
• CAS: 34035-39-7
• 化学式: C₁₈H₁₆N₂OS
• 分子量: 308.404
• InChiKey: CUDXEBHVOITLIT-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212 °C(Solv: ethanol (64-17-5))
• 沸点：
  536.8±60.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-diphenyl-2H,3H,4H-3-hydroxytetrahydroimidazo[2,1-b][1,3]thiazine 在 三溴化磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以57%的产率得到6-Bromo-2,3-diphenyl-6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazine
  参考文献：
  名称：

  咪唑并[2,1-b]-和苯并咪唑并[2,1-b] [1.3]噻嗪的3-卤代衍生物的合成

  摘要：

  DOI：

  10.1007/bf02253051
• 作为产物：
  描述：

  2-[(2,3-dihydroxyprop-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 0.07h， 以70%的产率得到6,7-diphenyl-2H,3H,4H-3-hydroxytetrahydroimidazo[2,1-b][1,3]thiazine
  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

• Regioselectivity of the reactions of 4,5-diphenylimidazole-2-thione with 1-chloro-2,3-epoxy-propane and 1-bromo-propene, efficient precursors for imidazo[2,1-<i>b</i>]thiazine and thiazole. Effect of microwave and solid support
  作者：Mohamed. R. Aouad、Nadje T. Rezki、El Sayed H. El Ahsry

  DOI：10.1002/jhet.5570450511

  日期：2008.9

  A regioselective allylation of 1 with allyl bromide in presence of triethylamine gave the S-allyl 8, while in presence of potassium carbonate led to the S,N-bis(allylated) derivative 9. The intramolecular ring closure of 8 in presence of sulfuric acid afforded the imidazothiazole 16. Protection of the sulfur in 1 and subsequent reaction with allyl bromide gave the N-allylated derivative and with 2 gave

  在没有溶剂的微波（MW）照射下，固体支持物可以选择性地合成2,3-环氧-丙基-硫代咪唑4，并禁止其环化，从而使咪唑并[2,1- b ]噻嗪3发生反应。 4,5-二苯基咪唑-2-硫酮（1）与1-氯-2,3-环氧丙烷（2）。后者的形成需要成为其唯一产品的基本条件；碱性催化剂的变化改变了常规和微波（MW）条件下两种产物的比例。在三乙胺的存在下，用烯丙基溴对1进行区域选择性烯丙基化，得到S-烯丙基8，而在碳酸钾的存在下导致S，N-双（烯丙基化）衍生物9。在硫酸存在下的分子内8的闭环得到咪唑并噻唑16。在1中保护硫，然后与烯丙基溴反应，得到N-烯丙基化衍生物，与2反应得到N-3-氯-丙-1-基衍生物，这为形成3和4的优选路线提供了线索。理论上已经通过使用AM1方法研究了1与2的烷基化过程中遇到的反应性。
• New synthesis of the 1,3-thiazine ring system
  作者：Howard Alper、Edmund C. H. Keung

  DOI：10.1021/jo00974a047

  日期：1972.5
• Korotkikh, N. I.; Aslanov, A. F.; Shvaika, O. P., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 8, p. 1525 - 1531
  作者：Korotkikh, N. I.、Aslanov, A. F.、Shvaika, O. P.

  DOI：——

  日期：——
• KOROTKIX, N. I.;ASLANOV, A. F.;SHVAJKA, O. P., ZH. ORGAN. XIMII, 26,(1990) N, S. 1761-1769
  作者：KOROTKIX, N. I.、ASLANOV, A. F.、SHVAJKA, O. P.

  DOI：——

  日期：——