(Z)-3-(benzylamino)-3-(methylthio)-1-phenylprop-2-en-1-one | 81376-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-(benzylamino)-3-(methylthio)-1-phenylprop-2-en-1-one
• 英文别名: (Z)-3-(benzylamino)-3-methylsulfanyl-1-phenylprop-2-en-1-one
• CAS: 81376-51-4
• 化学式: C₁₇H₁₇NOS
• 分子量: 283.394
• InChiKey: PBRUUMOQAAASIH-ATVHPVEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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)-3-(benzylamino)-3-(methylthio)-1-phenylprop-2-en-1-one 在 亚硝酰氯 作用下， 以 吡啶 、 乙醚 为溶剂， 反应 2.0h， 以75%的产率得到4-benzoyl-5-methylthio-2-phenylimidazole
  参考文献：
  名称：

  通过β-硫代-β-氨基-α，β-不饱和酮的直接亚硝化合成新型功能化的羟基亚氨基亚胺及其进一步的转化：咪唑，喹喔啉和噻唑衍生物的新通用合成方法

  摘要：

  已从相应的新型功能化1,2-羟基亚氨基亚胺（2），（5）和（）合成了合成咪唑（3），（10），喹喔啉（6）和噻唑（9）衍生物的新通用方法。8）通过用亚硝酰氯将β-硫代-β-氨基-α，β-不饱和酮直接亚硝化而获得。

  DOI：

  10.1039/c39840000430

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。
• Aza-Annulation of Polarized N,S- and N,N-Ketene Acetals with Itaconic Anhydride: Synthesis of Novel Functionalized 1,2,3,4-Tetrahydro-2-pyridones and Related Azabicycles
  作者：Hiriyakkanavar Ila、Hiriyakkanavar Junjappa、Sriparna Chakrabarti、Kausik Panda、Nimesh C. Misra

  DOI：10.1055/s-2005-868491

  日期：——

  Synthesis of novel highly functionalized 2-oxo-(1,2,3,4-tetrahydropyridin-3-yl)acetic acids has been described via aza-­annulation of both acyclic and cyclic α-oxo- and α-nitro-N,S- and -N,N-ketene acetals with itaconic anhydride.

  已描述通过与伊托酸酐反应的非环状和环状α-氧基和α-硝基-N,S-和-N,N-酮酯进行氮杂环化合成新型高度功能化的2-氧-(1,2,3,4-四氢吡啶-3-基)乙酸。
• 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 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。
• Cycloaddition of Aroyl/Acylketene<i>S,N</i>-Acetals with Tosyl Azide: Synthesis of Novel 4-Aroyl/Acyl-5-amino-1<i>H</i>-1,2,3-triazoles and 3,4-Annulated 1,2,3-Triazoles
  作者：R. T. Chakrasali、H. Ila、H. Junjappa

  DOI：10.1055/s-1988-27728

  日期：——

  Cycloaddition of aroyl- and acylketene S,N-acetals 1a-l with tosyl azide 2 under alkaline conditions affords novel regiospecifically substituted 4-aroyl/acyl-1-phenyl/alkyl-5-tosylamino-1H-1,2,3-triazoles 5a-1. Some of them (5a-e, g, h) are shown to undergo facile detosylation in the presence of concentrated sulfuric acid to give the corresponding 5-aminotriazoles 6a-e, g, h in excellent yields. The reaction of cyclic S,N-acetals 8a-c with 2 in dioxane at higher temperature yields the corresponding bicyclic 3-aroyl-5,6-dihydrothiazolo[3,2-c] [1,2,3]-triazoles 10a-c in good yields.

  在碱性条件下，芳基和酰基乙烯基 S,N-乙醛 1a-l 与甲苯基叠氮化物 2 环加成，可得到新的区域特异性取代的 4-芳酰基/酰基-1-苯基/烷基-5-对甲苯磺酸氨基-1H-1,2,3-三唑 5a-1。研究表明，其中一些（5a-e、g、h）在浓硫酸存在下容易发生去甲基化反应，从而以极好的收率得到相应的 5-氨基三唑 6a-e、g、h。环状 S,N-乙醛 8a-c 与 2 在二噁烷中于较高温度下反应，可得到相应的双环 3-芳酰基-5,6-二氢噻唑并[3,2-c] [1,2,3]- 三唑 10a-c，收率很高。