5-acetyl-4-methyl-2-imino-3-phenyl-2,3-dihydrothiazole | 57591-76-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetyl-4-methyl-2-imino-3-phenyl-2,3-dihydrothiazole
• 英文别名: 3-Phenyl-4-methyl-5-acetyl-2-imino-thiazolin；1-(2-imino-4-methyl-3-phenyl-2,3-dihydro-thiazol-5-yl)-ethanone；5-Acetyl-2-imino-4-methyl-3-phenyl-4-thiazolin；1-(2-Imino-4-methyl-3-phenyl-1,3-thiazol-5-yl)ethanone
• CAS: 57591-76-1
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: LHRCXENJKFXMBB-UHFFFAOYSA-N

物化性质

• 熔点：
  128-129 °C
• 沸点：
  361.1±52.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  69.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-acetyl-4-methyl-2-imino-3-phenyl-2,3-dihydrothiazole 在 一水合肼 作用下， 以 水 为溶剂， 反应 0.5h， 以31%的产率得到Bis-(3,5-dimethylpyrazol-4-yl)-disulfid
  参考文献：
  名称：

  Heterocyclenbildung mit Enaminen

  摘要：

  Aminoacrylderivatives (1) and Br2/NH4SCN form iminothiazolinones 3 a-c and with chlorosulfonylisocyanate thiadiazinonedioxide 8. Reaction of 3 a with hydrazine yields disulfide 6. Compound 2 and PCl3 yield diazaphosphorines 7 a-c. By reaction of pyrimidinone 9 with NaOCl, HCl/H2O2 or Br2/NH4SCN dichloropyrimidinone 10, dichlorooxaziridine 16, and thiocyanate 13 are formed. Octahydroquinazolinone (17) and NaOCl or H2O2/HCl form chloroderivatives 18, 19 and 20, 18 with peracid oxaziridine 22. Compounds 16, 21, 22 and 13 with NaOCl form N-chloroderivatives 23, 24, 25 and 26 resp.

  DOI：

  10.1002/prac.19923340813
• 作为产物：
  描述：

  [(Z)-2-anilino-4-oxopent-2-en-3-yl] thiocyanate 生成 5-acetyl-4-methyl-2-imino-3-phenyl-2,3-dihydrothiazole
  参考文献：
  名称：

  TOKUMITSU TAKAO; HYASHI TAKAYUKI, YUKI GOSEHJ KAGAKU KEKAJSI, J. SUNTN. ORG. CHEM. JAR. , 1975, 33+

  摘要：

  DOI：

文献信息

• Study on condensation of N-aryl thioureas with 3-bromo-acetylacetone: Synthesis of aminothiazoles and iminodihydrothiazoles, and their in vitro antiproliferative activity on human cervical cancer cells
  作者：Hai-Bo Shi、Shi-Jie Zhang、Yan-Fang Lin、Wei-Xiao Hu、Chao-Ming Cai

  DOI：10.1002/jhet.602

  日期：2011.9

  The condensation of N‐aryl thioureas with 3‐bromo‐acetylacetone in neutral solvent acetone not only led to 5‐acetyl‐4‐methyl‐2‐(substituted anilino) thiazoles 3 but also 2‐imino‐3‐(substituted phenyl)‐4‐methyl‐5‐acetyl‐2,3‐dihydrothiazoles 4. Further study found that different reaction solvents displayed an important role toward the ratio of aminothiazoles 3 and iminodihydrothiazoles 4, and the reaction

  的缩合ñ -芳基与3-溴乙酰丙酮硫脲在中性溶剂丙酮不仅导致5-乙酰基-4-甲基-2-（取代的苯胺基）噻唑类3也2-亚氨基-3-（取代苯基） - 4-甲基-5-乙酰基-2,3-二氢噻唑4。进一步的研究发现，不同的反应溶剂对氨基噻唑3和亚氨基二氢噻唑4的比例具有重要作用，并且扩大了反应范围。提出了一种可能的机制，其中涉及溶剂效应和原位氢溴酸催化。一些选定的异构体在体外表现出中等水平对人类宫颈癌细胞系的抗增殖活性（Hela，Siha）。J.杂环化​​学。（2011）。
• Heterocyclenbildung mit Enaminen
  作者：Christian Bischoff、Edith Schr�der

  DOI：10.1002/prac.19923340813

  日期：——

  Aminoacrylderivatives (1) and Br2/NH4SCN form iminothiazolinones 3 a-c and with chlorosulfonylisocyanate thiadiazinonedioxide 8. Reaction of 3 a with hydrazine yields disulfide 6. Compound 2 and PCl3 yield diazaphosphorines 7 a-c. By reaction of pyrimidinone 9 with NaOCl, HCl/H2O2 or Br2/NH4SCN dichloropyrimidinone 10, dichlorooxaziridine 16, and thiocyanate 13 are formed. Octahydroquinazolinone (17) and NaOCl or H2O2/HCl form chloroderivatives 18, 19 and 20, 18 with peracid oxaziridine 22. Compounds 16, 21, 22 and 13 with NaOCl form N-chloroderivatives 23, 24, 25 and 26 resp.
• TOKUMITSU TAKAO; HYASHI TAKAYUKI, YUKI GOSEHJ KAGAKU KEKAJSI, J. SUNTN. ORG. CHEM. JAR. <YGKK-AE>, 1975, 33+
  作者：TOKUMITSU TAKAO、 HYASHI TAKAYUKI

  DOI：——

  日期：——