(Z)-3-(methylamino)-3-methylsulfanyl-1-phenylprop-2-en-1-one | 91787-80-3

• 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-(methylamino)-3-methylsulfanyl-1-phenylprop-2-en-1-one
• CAS: 91787-80-3
• 化学式: C₁₁H₁₃NOS
• 分子量: 207.296
• InChiKey: UHFFIMUHPKXNIL-FLIBITNWSA-N

物化性质

• 沸点：
  326.0±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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-(methylamino)-3-methylsulfanyl-1-phenylprop-2-en-1-one 在 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 10.0h， 生成 1,2-bis-(3-phenyl-7-methyl-4,5,6,7-tetrahydropyrazolo[3,4-d]pyrimidinyl)ethane
  参考文献：
  名称：

  一种新型新取代的1,2,3,4-四氢嘧啶的简便一锅合成方法第5部分†：双[（1-烷基/芳烷基）-5-苯甲酰基-6-甲硫基1,2,3,4-的合成四氢嘧啶基]烷和苯，双[3-苯基-7-甲基-4,5,6,7-四氢吡唑并[3,4- d ]-嘧啶基]烷和双[1-苄基-7-苯基-1,2 ，3,4-四氢吡唑并[1,5- a ]三嗪基]烷烃和苯

  摘要：

  通过N，S-缩醛与甲醛和二胺的反应合成了双1,2,3,4-四氢嘧啶基烷烃/苯2a-f。吡唑3a和3b与二胺和甲醛反应生成双-4,5,6,7-四氢吡唑并[3,4- d ]嘧啶基烷烃4a-b和双1,2,3,4-四氢吡唑并[1,5- a ]三嗪基烷烃和苯5a-c分别具有良好的收率。

  DOI：

  10.1002/jhet.5570420535

文献信息

• Substituted Nitrogen Heterocycles and Synthesis and Uses Thereof
  申请人：Petasis Nicos A.

  公开号：US20090247766A1

  公开（公告）日：2009-10-01

  The invention relates to a nitrogen heterocycle compound of formula 1: Also disclosed are a method of synthesizing the compound and use of the compound for treating various diseases and conditions.

  该发明涉及一种化学式为1的氮杂环化合物。还公开了一种合成该化合物的方法，以及利用该化合物治疗各种疾病和病况的用途。
• 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。
• Synthesis of novel functionalized hydroxyiminoimines by direct nitrosation of β-thio-β-amino-α,β- unsaturated ketones and their further transformations: new general syntheses for imidazole, quinoxaline, and thiazole derivatives
  作者：Azizur-Rahman Azizur-Rahman、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1039/c39840000430

  日期：——

  New general methods for the synthesis of imidazole (3), (10), quinoxaline (6), and thiazole (9) derivatives have been developed from the corresponding novel functionalized 1,2-hydroxyiminoimines (2), (5), and (8) obtained by direct nitrosation of β-thio-β-amino-α,β-unsaturated ketones with nitrosyl chloride.

  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。
• 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。