ethyl 4-methyl-3-phenyl-2-thioxo-2,3-dihydrothiazole-5-carboxylate | 3161-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-methyl-3-phenyl-2-thioxo-2,3-dihydrothiazole-5-carboxylate
• 英文别名: 3-phenyl-4-methyl-5-ethoxycarbonyl-3H-thiazole-2-thione；4-methyl-3-phenyl-2-thioxo-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester；2-Thio-3-phenyl-4-methyl-5-carbethoxy-Δ⁴-thiazolin；4-Methyl-3-phenyl-5-ethoxycarbonyl-thiazolin-thion-(2)；Ethyl 4-methyl-3-phenyl-2-thioxo-2,3-dihydro-1,3-thiazole-5-carboxylate；ethyl 4-methyl-3-phenyl-2-sulfanylidene-1,3-thiazole-5-carboxylate
• CAS: 3161-80-6
• 化学式: C₁₃H₁₃NO₂S₂
• mdl: MFCD01557908
• 分子量: 279.384
• InChiKey: YNFUUULESNFPMM-UHFFFAOYSA-N

物化性质

• 熔点：
  161-162 °C
• 沸点：
  390.8±52.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)
• 溶解度：
  3.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  86.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-methyl-3-phenyl-2-thioxo-2,3-dihydrothiazole-5-carboxylate 生成 2-hydrazono-4-methyl-3-phenyl-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Bulka,E. et al., Chemische Berichte, 1965, vol. 98, p. 259 - 273

  摘要：

  DOI：
• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以87%的产率得到ethyl 4-methyl-3-phenyl-2-thioxo-2,3-dihydrothiazole-5-carboxylate
  参考文献：
  名称：

  Synthesis and heterocyclization of dithiocarbamoylacetoacetic esters and anilides

  摘要：

  DOI：

  10.1007/bf02290851

文献信息

• 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。
• 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.
• Tripathy,H. et al., Journal of the Indian Chemical Society, 1973, vol. 50, p. 417 - 419
  作者：Tripathy,H. et al.

  DOI：——

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

  DOI：——

  日期：——