3-cyclohexyl-4,5-diphenyl-1H-imidazole-2-thione | 79713-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-cyclohexyl-4,5-diphenyl-1H-imidazole-2-thione
• CAS: 79713-60-3
• 化学式: C₂₁H₂₂N₂S
• 分子量: 334.485
• InChiKey: HGENFECHCLLYQR-UHFFFAOYSA-N

物化性质

• 熔点：
  316-317 °C
• 沸点：
  483.4±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  3-cyclohexyl-4,5-diphenyl-1H-imidazole-2-thione 、 丁炔二酸二甲酯 以 甲醇 为溶剂， 反应 1.0h， 以65%的产率得到(Z)-2-[(1-cyclohexyl-4,5-diphenyl-1H-imidazol-2-yl)sulfanyl]but-2-enedioic acid dimethyl ester
  参考文献：
  名称：

  Mloston; Gendek; Linden, Polish Journal of Chemistry, 2008, vol. 82, # 8, p. 1561 - 1569

  摘要：

  DOI：
• 作为产物：
  描述：

  Alpha-联苯酰一肟 在 2,2,4,4-tetramethyl-3-thioxocyclobutanone 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 7.0h， 生成 3-cyclohexyl-4,5-diphenyl-1H-imidazole-2-thione
  参考文献：
  名称：

  First Examples of Reactions of AzoleN-Oxides with Thioketones: A Novel Type of Sulfur-Transfer Reaction

  摘要：

  The reactions of 1,4,5-trisubstituted imidazole 3-oxides 1a-k with cyclobutanethiones 5a,b in CHCl3 at room temperature give imidazole-2(3H)-thiones 9a-k in high yield. The second product formed in this reaction is 2,2,4,4-tetramethylcyclobutane-1,3-dione (6a; Scheme 2). Similar reactions occur with 1 and adamantanethione (5c) as thiocarbonyl compound, as well as with 1,2,4-triazole-4-oxide derivative 10 and 5a (Scheme 3). A reaction mechanism by a two-step formation of the formal cycloadduct of type 7 via zwitterion 16 is proposed in Scheme 5. Spontaneous decomposition of 7 yields the products of this novel sulfur-transfer reaction. The starting imidazole 3-oxides are conveniently prepared by heating a mixture of 1,3,5-trisubstituted hexahydro-1,3,5-triazines 3 and alpha-(hydroxyimino) ketones 2 in EtOH (cf: Scheme 1). As demonstrated in the case of 9d, a 'one-pot' procedure allows the preparation of 9 without isolation of the imidazole 3-oxides 1. The reaction of Ic with thioketene 12 leads to a mixture of four products (Scheme 4). The minor products, 9c and the ketene 15, result from an analogous sulfur-transfer reaction (Path a in Scheme 5), whereas the parent imidazole 14 and thiiranone 13 are the products of an oxygen-transfer reaction (Path b in Scheme 5).

  DOI：

  10.1002/(sici)1522-2675(19980909)81:9<1585::aid-hlca1585>3.0.co;2-n

文献信息

• Reactions of Stable -Chlorosulfanyl Chlorides with CS-Functionalized Compounds
  作者：Agnieszka Majchrzak、Aleksandra Janczak、Grzegorz Mlostoń、Anthony Linden、Heinz Heimgartner

  DOI：10.1002/hlca.200390183

  日期：2003.6

  The smooth reaction of 3-chloro-3-(chlorosulfanyl)-2,2,4,4-tetramethylcyclobutanone (3) with 3,4,5-trisubstituted 2,3-dihydro-1H-imidazole-2-thiones 8 and 2-thiouracil (10) in CH2Cl2/Et3N at room temperature yielded the corresponding disulfanes 9 and 11 (Scheme 2), respectively, via a nucleophilic substitution of Cl− of the sulfanyl chloride by the S-atom of the heterocyclic thione. The analogous reaction

  3-氯-3-（氯硫烷基）-2,2,4,4-四甲基环丁酮（3）与3,4,5-三取代的2,3-二氢-1 H-咪唑-2-硫酮8和2-硫尿嘧啶（10）在CH 2氯2 / ET 3 ñ在室温下得到相应的disulfanes 9和11（方案2），分别通过氯的亲核取代-通过的所述S-原子的硫烷基氯化杂环硫酮。3-环己基-2,3-二氢-4,5-二苯基-1H-咪唑-2-硫酮的类似反应（8b）与10与氯二硫烷基衍生物16分别产生相应的三硫烷17和18（方案4）。另一方面，3和4,4-二甲基-2-苯基-1,3-噻唑-5（4 H）-硫酮（12）在CH 2 Cl 2中的反应仅得到4,4-二甲基-2 -苯基-1,3-噻唑-5（4 H）-one（13）和三硫原酸酯衍生物14（一种双二硫烷），收率低（方案3）。在-78°时只有双（1-氯-2,2,4,4-四甲基-3-氧代环丁基）聚硫醚15形成了。即使在-78°，CH 2 Cl
• Recyclization of 4,5-diphenyloxazolin-2-one and -2-thione under the influence of amines
  作者：V. B. Kalcheva、L. I. Tsvetanska

  DOI：10.1007/bf00503651

  日期：1981.8
• KALCHEVA, V. B.;TSVETANSKA, L. I., XIMIYA GETEROTSIKL. SOEDIN., 1981, N 8, 1028-1030
  作者：KALCHEVA, V. B.、TSVETANSKA, L. I.

  DOI：——

  日期：——