1-(3-Methylphenyl)-2-[5-methyl-1,3,4-thiadiazol-2-yl]ethanon | 187390-41-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-Methylphenyl)-2-[5-methyl-1,3,4-thiadiazol-2-yl]ethanon
• 英文别名: 1-(3-Methylphenyl)-2-(5-methyl-1,3,4-thiadiazol-2-yl)ethanone
• CAS: 187390-41-6
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: BDAMKVSCKGXDOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3-Bis(dimethylamino)-1-phenyl-prop-1-in 、 1-(3-Methylphenyl)-2-[5-methyl-1,3,4-thiadiazol-2-yl]ethanon 以 四氢呋喃 为溶剂， 以79%的产率得到(2Z,4E)-5-Dimethylamino-2-(5-methyl-[1,3,4]thiadiazol-2-yl)-5-phenyl-1-m-tolyl-penta-2,4-dien-1-one
  参考文献：
  名称：

  Orthoamide. L. Beiträge zur Chemie von Propiolaldehydaminalen - Synthesen und Umsetzungen zu Push-Pull-substituierten Buta-1,3-dienen, Cyclobutanen sowie vinylogen Amidiniumsalzen und 1,2,3-Triazolen

  摘要：

  Tert-butylaminalester 5 reacts with terminal alkynes to give aminals of substituted propiolaldehydes 3c,d. The aminal 3a is accessible from N,N,N,N'-tetramethylformamidinium chloride (7b) and sodium acetylide. The aminals 3b,c can also be prepared from bis(dimethylamino)acetonitrile 8 and terminal alkynes in the presence of sodium hydride. The nitrile 8 is also useful for the preparation of the bis-aminal of acetylenedialdehyde 6. The aminal 3e can be transaminated by heating with secondary amines to give the aminals 3f-i. The aminals 3a-i react with strong CH2-acidic compounds (pK(a) between 9 and 14) to give the 1-dialkylamino-1,3-butadienes 10. The isomeric 1-dialkylamino-butadienes 18 can be obtained from the condensation of the CH-acidic cinnamic acid derivatives 19 with dimethylformamidedimethylacetal. CH and NH-acidic compounds as cyanacetamide react with the aminals 3c,e exclusively with the acidic methylene group to produce the enamines 10h,t. The acylformamidine 21 can be obtained from 10t and tert-butylaminalester 5. The pyridone 22 is accessible from the condensation product 10h by thermal cyclization. The pyrido[2,3-d]pyrimidine 26 is formed in the reaction of the 6-amino-uracile 23 with the aminal 3a. In an unexpected reaction the 1,2-bis(cyano-dialkylaminomethylene)-cyclobutanes 28a-d result from the action of trimethylsilylcyanide on the aminals 3e-h. The corresponding reaction with trimethylsilylisothiocyanate affords the vinylogous amidinium thiocyanates 34a,b. In the reaction of trimethylsilylazide and the aminals 3 are produced the 4-(dialkylaminomethylene)-4H-1,2,3-triazoles 38.

  DOI：

  10.1002/prac.19973390130
• 作为产物：
  描述：

  3-Methyl-benzoic acid (Z)-2-(5-methyl-[1,3,4]thiadiazol-2-yl)-1-m-tolyl-vinyl ester 在 盐酸 作用下， 以 异丙醇 为溶剂， 反应 8.0h， 以86%的产率得到1-(3-Methylphenyl)-2-[5-methyl-1,3,4-thiadiazol-2-yl]ethanon
  参考文献：
  名称：

  Die Synthese von 2-Methyl-5-phenacyl-1,3,4-thiadiazolen / The Synthesis of 2-Methyl-5-phenacyl-1,3,4-thiadiazoles

  摘要：

  关键词 2,5-二甲基-1,3,4-噻二唑 (1a) 在过量氢化钠存在下缩合生成芳香族羧酸酯 8a - u，生成烯醇钠，水解生成苯甲酰基-1,3， 4-噻二唑 9a - u。在三乙胺存在下，芳族羧酸氯化物对 1a 的作用导致形成二酰化噻二唑衍生物 16 和 18 的混合物。在某些情况下，纯 3-酰基-苯亚基-2,3-二氢-1,3，可以分离4-噻二唑16。通常化合物16在高沸点溶剂中加热重排得到烯醇苯甲酸酯18。二酰化噻二唑16和18的水解产生苯甲酰噻二唑9a、c、d、g-j、v、w。

  DOI：

  10.1515/znb-2004-0403