(Z)-4-Ethylamino-4-methylsulfanyl-but-3-en-2-one | 81376-49-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: (Z)-4-Ethylamino-4-methylsulfanyl-but-3-en-2-one
• 英文别名: (Z)-4-(ethylamino)-4-methylsulfanylbut-3-en-2-one
• CAS: 81376-49-0
• 化学式: C₇H₁₃NOS
• 分子量: 159.252
• InChiKey: AMOBKCCJGUYWAX-ALCCZGGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-4-Ethylamino-4-methylsulfanyl-but-3-en-2-one 、 丙二酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以35%的产率得到8-Acetyl-6-ethyl-4-hydroxy-7-methylsulfanyl-6H-pyrano[3,2-c]pyridine-2,5-dione
  参考文献：
  名称：

  Reaction of AcylketeneS,N-Acetals with Malonyl Chloride: Synthesis of Novel 1,5-Substituted 4-Hydroxy-6-methylthio-2 (1H)-pyridones and 6,8-Substituted 4-Hydroxy-7-methylthio-2,5-dioxo-5,6-dihydro-2H-pyrano [3,2-c] pyridines

  摘要：

  酰基烯酮S,N-缩醛1与一当量丙二酰氯在三乙胺存在下反应，以良好的收率得到新型1,5-取代的4-羟基-6-甲硫基-2(1H)-吡啶酮3。然而，在过量丙二酰氯（三当量）存在下，反应进一步进行，以中等收率得到相应的吡喃并[3,2-c]吡啶酮衍生物4。

  DOI：

  10.1055/s-1988-27476

文献信息

• Reaction of Polarized Ketene<i>S,N</i>-Acetals with Bromoacetaldehyde Diethyl Acetal: Synthesis of 1-Substituted 3-Acyl- and 3-Nitro-2-methylthiopyrroles and 1,2-Annulated 3-Acylpyrroles
  作者：Akhilesh K. Gupta、R. T. Chakrasali、H. Ila、H. Junjappa

  DOI：10.1055/s-1989-27179

  日期：——

  A regiospecific route for 1-substituted 3-acyl- and 3-nitro-2-methylthiopyrroles 3a-l and the corresponding 1,2-annulated 3-acylpyrroles 5a-c has been developed by reaction of acyl- and nitroketene S,N-acetals 1a-l and 4a-c with bromoacetaldehyde diethyl acetal in dimethylformamide.

  已开发出一种区域选择性合成1-取代的3-酰基-和3-硝基-2-甲基噻吩吡咯3a-l及相应的1,2-环化3-酰基吡咯5a-c的方法，该方法通过在二甲基甲酰胺中将酰基和硝基酮烯S,N-乙酰酸酯1a-l和4a-c与溴乙醛二乙基乙acetals进行反应实现。
• Cyclocondensation of Acylketene<i>S</i>,<i>N</i>- and<i>N</i>,<i>N</i>-acetals with Maleic Anhydride and Maleimide: A Facile One-Step Synthesis of Pyrano [3,4-<i>c</i>]pyrrole, Pyrrolo [3,4-<i>c</i>]pyridine and Condensed Pyrrole Derivatives
  作者：Akhilesh K. Gupta、H. Ila、H. Junjappa

  DOI：10.1055/s-1988-27544

  日期：——

  The acylketene S,N-acetals 1a-c react with maleic anhydride (2) in refluxing acetonitrile to give the corresponding 3-pyrrolin-2-one-3-acetic acid derivatives 3a-c in good yields. Condensation of S,N-acetals 1a-j and 2 in presence of acetic anhydride directly afforded the corresponding 2-substituted-3-methylthio-4-aryl (or methyl)-1,6-dioxo- 2,3-dihydropyrano[3,4-c]pyrroles 4 a-j in excellent yields. The reaction of cyclic S,N- (5a-c) and N,N- (5d-f) acetals with 2 in refluxing acetonitrile gave the corresponding pyrrolo[2,1-b]thiazole (6a-c) and pyrrolo[1,2-a]imidazole (6d-f) derivatives, respectively, in good yields. Similarly, the condensation of S,N-acetals 1a and 1d with maleimide directly yielded the respective pyrrolo[3,4-c]pyridine derivatives 9a and 9b, while the corresponding pyrrolinone-3-acetamide derivatives 8a and 8b were obtained under similar conditions, when the reaction time was reduced.

  酰基烯酮S,N-缩醛1a-c与马来酸酐(2)在回流乙腈中反应，以良好的收率得到相应的3-吡咯啉-2-酮-3-乙酸衍生物3a-c。 S,N-缩醛1a-j和2在乙酸酐存在下缩合直接得到相应的2-取代-3-甲硫基-4-芳基(或甲基)-1,6-二氧代-2,3-二氢吡喃[3 ,4-c]吡咯 4 a-j 具有优异的产率。环状S,N-(5a-c)和N,N-(5d-f)缩醛与2在回流乙腈中反应，得到相应的吡咯并[2,1-b]噻唑(6a-c)和吡咯并[1 ,2-a]咪唑(6d-f)衍生物，分别具有良好的收率。 类似地，S,N-缩醛1a和1d与马来酰亚胺缩合直接得到各自的吡咯并[3,4-c]吡啶衍生物9a和9b，而相应的吡咯啉酮-3-乙酰胺衍生物8a和8b在类似条件下得到，当反应时间减少时。
• Reaction of<i>a</i>-Ketoketene<i>S,N</i>-Acetals with Cyanoacetamide: A New General Method for Substituted and Fused 4-(<i>N</i>-Alkylamino-,<i>N</i>-Arylamino-, or<i>N</i>-Morpholino)-3-cyano-2(1<i>H</i>)-pyridones
  作者：V. Aggarwal、G. Singh、H. Ila、H. Junjappa

  DOI：10.1055/s-1982-29751

  日期：——
• Gupta, Akhilesh K.; Reddy, Kethiri R.; Ila, Hiriyakkanavar, Journal of the Chemical Society. Perkin transactions I, 1995, # 13, p. 1725 - 1728
  作者：Gupta, Akhilesh K.、Reddy, Kethiri R.、Ila, Hiriyakkanavar、Junjappa, Hiriyakkanavar

  DOI：——

  日期：——
• Reaction of Acylketene<i>S,N</i>-Acetals with Malonyl Chloride: Synthesis of Novel 1,5-Substituted 4-Hydroxy-6-methylthio-2 (1<i>H</i>)-pyridones and 6,8-Substituted 4-Hydroxy-7-methylthio-2,5-dioxo-5,6-dihydro-2<i>H</i>-pyrano [3,2-<i>c</i>] pyridines
  作者：R. T. Chakrasali、H. Ila、H. Junjappa

  DOI：10.1055/s-1988-27476

  日期：——

  The acylketene S,N-acetals 1 react with one equivalent of malonyl chloride in the presence of triethylamine to give novel 1,5-substituted 4-hydroxy-6-methylthio-2(1H)-pyridones 3 in good yields. However, in the presence of excess of malonyl chloride (three equivalents), the reaction proceeds further to give the corresponding pyrano[3,2-c] pyridones derivatives 4 in moderate yields.

  酰基烯酮S,N-缩醛1与一当量丙二酰氯在三乙胺存在下反应，以良好的收率得到新型1,5-取代的4-羟基-6-甲硫基-2(1H)-吡啶酮3。然而，在过量丙二酰氯（三当量）存在下，反应进一步进行，以中等收率得到相应的吡喃并[3,2-c]吡啶酮衍生物4。