1-methyl-4,5-diphenyl-1,3-dihydro-imidazole-2-thione | 16116-43-1

• 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-methyl-4,5-diphenyl-1,3-dihydro-imidazole-2-thione
• 英文别名: 1,3-dihydro-1-methyl-4,5-diphenyl-2H-imidazole-2-thione；1-Methyl-4,5-diphenyl-4-imidazoline-2-thione；3-methyl-4,5-diphenyl-1H-imidazole-2-thione
• CAS: 16116-43-1
• 化学式: C₁₆H₁₄N₂S
• 分子量: 266.367
• InChiKey: BGRLRLCWDPJVML-UHFFFAOYSA-N

物化性质

• 熔点：
  273-275 °C(Solv: methanol (67-56-1))
• 沸点：
  408.3±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-methyl-4,5-diphenyl-1,3-dihydro-imidazole-2-thione 在 一水合肼 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 100.0h， 生成 N-(4-methoxyphenyl)-2-{[(1-methyl-4,5-diphenyl-1H-imidazol-2-yl)sulfanyl]acetyl}hydrazinecarboselenoamide
  参考文献：
  名称：

  源自咪唑基碳酰肼的新型硒亚氨基脲

  摘要：

  咪唑基碳酰肼，即3-氧代咪唑-4-碳酰肼1和2-[（（咪唑-2-基）硫烷基]乙酰]乙酰肼6，在室温下与MeOH中的芳基异亚硒酸酯4反应，得到相应的硒代氨基碳酰肼5和7，分别以高收成。在空气中将7b在DMF中加热到100°，通过环化和正式消除H 2 Se形成1,3,4-恶二唑8a。加热4a和6b的混合物后，也获得了产物8a在相同条件下。另一方面，在回流下加热7c的MeOH溶液时，发生环化反应，得到相应的1,2,4-三唑-3-硒酮9b。再次，当将4b和6b的混合物在MeOH中加热时，形成相同的产物。令人惊讶的是，在相同条件下，类型5的硒代氨基脲的类似环化反应失败，仅观察到分解。X射线晶体学已经确定了7a，7d和9b的结构。

  DOI：

  10.1002/hlca.201200620
• 作为产物：
  描述：

  1-methyl-4,5-diphenyl-1H-imidazole 3-oxide 在 2,2,4,4-tetramethyl-3-thioxocyclobutanone 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以79%的产率得到1-methyl-4,5-diphenyl-1,3-dihydro-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

• Imidazole compounds and their use as transglutaminase inhibitors
  申请人：Merck & Co., Inc.

  公开号：US05030644A1

  公开（公告）日：1991-07-09

  Imidazole compounds including imidazoles and imidazolium salts, and their use as transglutaminase inhibitors are disclosed.

  咪唑化合物，包括咪唑和咪唑盐，以及它们作为转谷氨酰胺酶抑制剂的用途被披露。
• Acyl-CoA: cholesterol O-acyl transferase (ACAT) inhibitors. 1. 2-(Alkylthio)-4,5-diphenyl-1H-imidazoles as potent inhibitors of ACAT
  作者：Neil V. Harris、Andrew W. Bridge、Raymond C. Bush、Edward C. J. Coffee、Donald I. Dron、Mark F. Harper、Michael J. Ashton、David J. Lythgoe、Christopher Smith

  DOI：10.1021/jm00101a016

  日期：1992.11

  potent, bioavailable ACAT inhibitor may have beneficial effects in the treatment of atherosclerosis by (i) reducing the absorption of dietary cholesterol, (ii) reducing the secretion of very low density lipoproteins into plasma from the liver, and (iii) preventing the transformation of arterial macrophages into foam cells. We have found that a mevalonate derivative 2, which contains a 4,5-diphenyl-1H-imidazol-2-yl

  生物有效的有效ACAT抑制剂可通过（i）减少饮食中胆固醇的吸收，（ii）减少极低密度脂蛋白从肝脏向血浆的分泌以及（iii）防止转化而对动脉粥样硬化产生有益作用巨噬细胞进入泡沫细胞。我们已经发现，含有4,5-二苯基-1H-咪唑-2-基部分的甲羟戊酸酯衍生物2在体外抑制大鼠肝微粒体ACAT，并在胆固醇喂养的大鼠中产生明显的降胆固醇作用。2的类似物的结构活性关系表明，4,5-二苯基-1H-咪唑部分是抑制大鼠微粒体ACAT的药效基团。
• Trapping of a Thiocarbonyl Ylide with Imidazolethiones, Pyrimidinethione, and Thioamides
  作者：Grzegorz Mlostoń、Tomasz Gendek、Anthony Linden、Heinz Heimgartner

  DOI：10.1002/(sici)1522-2675(19990210)82:2<290::aid-hlca290>3.0.co;2-p

  日期：1999.2.10

  The reactions of 1,1,3,3-tetramethyl-8-thia-5,6-diazaspirol[3.4]oct-5-en-2-one (1a) with imidazole-2-thiones 3 and pyrimidine-2(1H)-thione (6) in CHCl3 at 40-50 degrees yield 2,2,4,4-tetramethylcyclobutanone dithioacetals of type 4 and 7 respectively, by interception of the intermediate thiocarbonyl ylide 2a (Scheme 2).; product by 1,3-dipolar electrocyclization of 2a. When thioacetamide (8a) and Thiirane 5 is formed as a minor thiobenzamide (8b) are used as trapping reagents. the primary adduct 10 undergoes a spontaneous cyclization by intramolecular nucleophilic addition of the imino group at the carbonyl group to yield bicyclic products of type 9. The structure of 9a has been established by X-ray crystallography.
• Stock; Hetzheim, Pharmazie, 1987, vol. 42, # 3, p. 157 - 159
  作者：Stock、Hetzheim

  DOI：——

  日期：——
• von Nuhn,P.; Wagner,G., Journal fur praktische Chemie (Leipzig 1954), 1970, vol. 312, p. 90 - 96
  作者：von Nuhn,P.、Wagner,G.

  DOI：——

  日期：——