5-benzoyl-2-N,N-dimethylamino-1,3-thiazole | 129865-58-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-benzoyl-2-N,N-dimethylamino-1,3-thiazole
• 英文别名: (2-dimethylaminothiazol-5-yl) phenyl ketone；[2-(Dimethylamino)-1,3-thiazol-5-yl]-phenylmethanone
• CAS: 129865-58-3
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: IHRPRYDDVXPRAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 以58%的产率得到5-benzoyl-2-N,N-dimethylamino-1,3-thiazole
  参考文献：
  名称：

  戴斯-马丁高碘烷试剂通过烯胺酮和 KSCN 的级联环化合成噻唑-5-甲醛

  摘要：

  开发了用于合成噻唑-5-甲醛的叔烯胺酮与硫氰酸钾的戴斯-马丁高碘烷 (DMP) 试剂介导的反应。产物形成涉及C=C双键的级联羟基硫氰化、C≡N键的分子内加氢胺化和通过在酮羰基位点缩合的噻唑环化，代表了烯胺酮与硫氰酸盐之间反应的新反应途径。DMP 在介导自由基硫氰化和通过掩蔽反应过程中原位生成的甲酰基诱导非常规选择性噻唑-5-甲醛形成方面发挥双重作用。

  DOI：

  10.1021/acs.joc.2c01881

文献信息

• Orthoamide. IL. Umsetzungen von Orthoamid-Derivaten mit Schwefel und Selen, Synthesen von 1,3-Thiazol- und 1,3-Selenazolderivaten
  作者：W. Kantlehner、Michael Hauber、Markus Vettel

  DOI：10.1002/prac.19963380180

  日期：——

  N,N-Dimethylformamide acetal reacts with elemental selenium to give a mixture of selenocarbonic acid derivatives 2 and 3, which can be converted to the pure N,N-dimethylcarbamidic acid Se-methylester 2 by treatment with methyl iodide. Analogously from the orthoformic acid derivatives 5 and 6 and selenium the N,N,N',N'-tetramethyl-selenurea 7 can be prepared. In the reaction of 12 with elemental sulfur and selenium the amidines 14 and 15, respectively, are formed. By treatment of 14 and 15 with alpha-halogenated carbonyl compounds and triethylamine the 1,3-thiazoles 18 and 1,3-selenazoles 19 can be prepared. The synthesis of the propynoic acid orthoamide 26b is described. 26b reacts with the guanidinium salt 24b to give the bis-orthoamide of butynedioic acid 20b. Other orthoamides of butynedioic acid 20b-20e can be synthesized from the orthoamide 20a by transamination. The thiolation of the orthoamides affords the bis-amidinium-dithiolates 21a-c, which can be alkylated to give the bis-amidinium salts 27. By treatment with alpha-halogene carbonyl compounds and triethylamine the dithiolates 21a-e are cyclized to give thieno [3,2b] thiophenes 28a-n. The quadrupoles 21 undergo cycloadditions with dimethyl-butynedioate which afford the bis(3H-thiophene-2 ylidenes) 29a-c. Treatment of 29a with methyl tosylate gives rise to the dithiophene 30a. The dithiophene 30b can be obtained by heating 21b with dimethylbutynedionate.
• Sawhney, Indu; Wilson, John R. H., Journal of the Chemical Society. Perkin transactions I, 1990, # 2, p. 329 - 331
  作者：Sawhney, Indu、Wilson, John R. H.

  DOI：——

  日期：——
• Facile Synthesis of 5-Acyl-2-amino- 1,3-thiazole by the Reaction of Thiaazadienes with a-Halo Ketones
  作者：Edward R. Biehl、Ramadas Sathunuru

  DOI：10.3987/com-04-10231

  日期：——
• Synthesis and characterisation of N,N-disubstituted 2-amino-5-acylthiophenes and 2-amino-5-acylthiazoles
  作者：Antje Noack、Horst Hartmann

  DOI：10.1016/s0040-4020(02)00083-2

  日期：2002.3

  Starting from halomethyl-ketones 8 and N,N'-persubstituted thioacrylamides 7 or their 2-aza analogues 11 a series of N,N-disubstituted 2-amino-5-acylthiophenes 10 and 2-amino-5-acylthiazoles 12, respectively are available. By starting from 1,3-dichloroacetone and using the same thioacrylamide derivatives 7 and 11 N,N-disubstituted 2-amino-5-(chloroacetyl)thiophenes 13 and 2-amino-5-(chloroacetyl)thiazoles 14 as well as N,N'-persubstituted bis-(2-amino-5-thienyl)ketones 15, 2-amino-5-thienyl-(2-amino-5-thiazolyl)ketones 16, and bis-(2-amino-5-thiazolyl)ketones 17, respectively are available. (C) 2002 Elsevier Science Ltd. All rights reserved.
• SAWHNEY, INDU;WILSON, JOHN R. H., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 329-331
  作者：SAWHNEY, INDU、WILSON, JOHN R. H.

  DOI：——

  日期：——