乙酮,1-(2,3-二氢-4-甲基-3-苯基-2-硫代-5-噻唑基)- | 156139-61-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 乙酮,1-(2,3-二氢-4-甲基-3-苯基-2-硫代-5-噻唑基)-
• 英文名称: 1-(4-methyl-3-phenyl-2-thioxo-2,3-dihydrothiazol-5-yl)ethan-1-one
• 英文别名: 1-(2,3-dihydro-4-methyl-3-phenyl-2-thioxothiazol-5-yl)-1-ethanone；3-phenyl-4-methyl-5-acetyl-3H-thiazole-2-thione；1-(4-Methyl-3-phenyl-2-thioxo-2,3-dihydro-1,3-thiazol-5-yl)ethanone；1-(4-methyl-3-phenyl-2-sulfanylidene-1,3-thiazol-5-yl)ethanone
• CAS: 156139-61-6
• 化学式: C₁₂H₁₁NOS₂
• mdl: MFCD03196766
• 分子量: 249.357
• InChiKey: NSKNVTYNXCJNAS-UHFFFAOYSA-N

物化性质

• 沸点：
  388.8±52.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)
• 溶解度：
  9.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酮,1-(2,3-二氢-4-甲基-3-苯基-2-硫代-5-噻唑基)- 在 哌啶 、 溴 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 5-(1-bromomethyl-2,2-dicyanovinyl)-4-methyl-3-phenylthiazole-2-(3H)-thione
  参考文献：
  名称：

  Mohareb, Rafat Milad; Wardakhan, Wagnat Wahba; El-Ablack, Fawzia Zakeria, Journal of Chemical Research, Miniprint, 1994, # 4, p. 747 - 760

  摘要：

  DOI：
• 作为产物：
  描述：

  ammonium N-phenyldithiocarbamate 、 3-氯-2,4-戊二酮 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以75%的产率得到乙酮,1-(2,3-二氢-4-甲基-3-苯基-2-硫代-5-噻唑基)-
  参考文献：
  名称：

  Elkholy, Y. M.; Elassar, A. A., Egyptian Journal of Chemistry, 1995, vol. 38, # 1, p. 67 - 76

  摘要：

  DOI：

文献信息

• Design, synthesis, X-ray analysis, and biological screening of new oxime and enaminone thiazoline-2-thione derivatives
  作者：Yahya I. Asiri、Abdullatif Bin Muhsinah、Abdulrhman Alsayari、Hazem A. Ghabbour、Zainab M. Almarhoon、Faiz A. Al-aizari、Kumar Venkatesan、Syed Tasqeeruddin、Syeda Shaheen Sulthana、Yahia N. Mabkhot

  DOI：10.1016/j.molstruc.2020.128977

  日期：2021.1

  series of 12 new thiazoline-2-thione derivatives (oxime and enaminone) were synthesized using an appropriate synthetic route. The characterization of the newly synthesized compounds was performed using X-ray single-crystal diffractometry, elemental analysis, 1H NMR, 13C NMR, IR, and MS techniques. These compounds were then evaluated for their biological activities against a variety of microbes and human

  摘要迫切需要开发更安全且不易产生耐药性的抗菌和抗癌药物。为此，使用适当的合成路线合成了一系列 12 种新的噻唑啉-2-硫酮衍生物（肟和烯胺酮）。使用 X 射线单晶衍射、元素分析、1H NMR、13C NMR、IR 和 MS 技术对新合成的化合物进行表征。然后评估这些化合物对多种微生物和人类癌细胞系的生物活性。我们的结果表明，制备的噻唑啉衍生物 4a、4b、6a、6c 和 7 显示出与标准药物相当的对烟曲霉的有效抗真菌活性。此外，除化合物 4b 外的所有噻唑啉衍生物，对白色念珠菌有效。测试的噻唑啉还显示出与所有测试的革兰氏阳性和革兰氏阴性细菌物种的标准药物相当的强效抗菌活性。合成的化合物 3、6b 和 7 对两种癌细胞系（HCT-116 和 HepG-2）的细胞毒性评估表明它们具有中等的细胞毒活性，其中化合物 6b 对 HCT-116 的细胞毒活性最好（IC50 = 79 µg/ml) 和 HepG-2
• Simple Method for the Preparation of Dialkyl (2,3-Dihydro-1,3-thiazol-2-YL)-phosphonates
  作者：Karolina Janikowska、Sławomir Makowiec

  DOI：10.1080/10426501003767110

  日期：2010.12.30

  Abstract A simple synthesis of dialkyl (2,3-dihydro-1,3-thiazol-2-yl)-phosphonates from thiazolium salts and trialkyl phosphites is described. The series of dialkyl (2,3-dihydro-1,3-thiazol-2-yl)-phosphonates with various substituents in positions 3, 4, and 5 of the thiazole ring were prepared. However, only phosphonates with an aryl on the nitrogen atom were stable enough for chromatographic purification

  摘要 描述了从噻唑鎓盐和亚磷酸三烷基酯简单合成 (2,3-二氢-1,3-噻唑-2-基)-膦酸二烷基酯的方法。制备了在噻唑环的 3、4 和 5 位具有各种取代基的二烷基 (2,3-二氢-1,3-噻唑-2-基)-膦酸酯系列。然而，只有在氮原子上带有芳基的膦酸酯才足够稳定以进行色谱纯化，尽管所有新的膦酸酯都对氧化非常敏感。我们努力在 Horner-Wadsworth-Emmons 反应中应用 (2,3-二氢-1,3-噻唑-2-基)-膦酸二烷基酯，但生成的膦酸反芳香阴离子即使在 -70°C 下也能迅速分解. 图形概要
• Synthesis, X-ray Analysis, Biological Evaluation and Molecular Docking Study of New Thiazoline Derivatives
  作者：Yahia N. Mabkhot、H. Algarni、Abdulrhman Alsayari、Abdullatif Bin Muhsinah、Nabila A. Kheder、Zainab M. Almarhoon、Faiz A. Al-aizari

  DOI：10.3390/molecules24091654

  日期：——

  A series of new thiazoline derivatives were synthesized. Structure analyses were accomplished employing 1H-NMR, 13C-NMR, X-ray and MS techniques. The in vitro antitumor activities were assessed against human hepatocellular carcinoma (HepG-2) and colorectal carcinoma (HCT-116) cell lines. The results revealed that the thiazolines 5b and 2c exhibited significant activity against the two cell lines. The

  合成了一系列新的噻唑啉衍生物。使用1H-NMR、13C-NMR、X-射线和MS技术完成结构分析。针对人肝细胞癌 (HepG-2) 和结直肠癌 (HCT-116) 细胞系评估了体外抗肿瘤活性。结果表明，噻唑啉 5b 和 2c 对两种细胞系表现出显着的活性。体外抗菌筛选表明，噻唑啉 2c、5b 和 5d 对沙门氏菌具有良好的抑制活性。此外，噻唑啉 2e 和 5b 对大肠杆菌的抑制活性与参考化合物庆大霉素的抑制活性相当。
• Chemical and Electrochemical Investigations on Thiazolium Salts: a Route to Powerful Donors in the Dithiadiazafulvalene Series.
  作者：Nathalie Bellec、David Guérin、Dominique Lorcy、Albert Robert、Roger Carlier、André Tallec、Tatsuya Shono、H. Toftlund

  DOI：10.3891/acta.chem.scand.53-0861

  日期：——

  Thiazolium salts have been investigated, chemically and electrochemically, in order to access to the redox properties of dithiadiazafulvalenes (DTDAF). As these donor molecules are oxygen-sensitive, it is more advisable to isolate them in their oxidized form as dicationic salts. Starting from a tetrathiazolium cation including two precursors groups, linked together with a conjugated spacer, a bis-DTDAF was formed and its electrochemical behavior studied.
• Heterocyclic thiones and their analogs in 1,3-dipolar cycloaddition: VII. Reaction of 4-methyl-1,3-thiazole-2(3H)-thiones with nitrile imines
  作者：E. V. Budarina、T. S. Dolgushina、M. L. Petrov、N. N. Labeish、A. A. Kol’tsov、V. K. Bel’skii

  DOI：10.1134/s1070428007100193

  日期：2007.10

  Reactions of 4-methyl-1,3-thiazole-2(3H)-thiones with various C,N-disubstituted nitrile imines occurred by the common [3+2]-cycloaddition scheme leading to the formation in general of stable spiro compounds. In reactions of o-nitrophenylnitrile imines acyclic compounds were the main products.