3-acetyl-4-methylthio-4-phenylaminobut-3-en-2-one | 15908-55-1

• 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: 3-acetyl-4-methylthio-4-phenylaminobut-3-en-2-one
• 英文别名: 1-Anilino-2-acetyl-1-methylthiobut-1-en-3-on；3-[anilino(methylsulfanyl)methylidene]pentane-2,4-dione
• CAS: 15908-55-1
• 化学式: C₁₃H₁₅NO₂S
• 分子量: 249.334
• InChiKey: WMRIIINRKHAEBI-UHFFFAOYSA-N

物化性质

• 沸点：
  423.4±45.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-acetyl-4-methylthio-4-phenylaminobut-3-en-2-one 在 哌啶 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 spiro-(4-amino-2,2-diacetyl-3-cyano-5,6,7,8-tetrahydronaphthyl)-1,2'-(4'-amino-10'b(H)-N-phenyl-1',3'-thiazino(5,4-c)coumarin)
  参考文献：
  名称：

  NEW SYNTHETIC APPROACHES TO CONDENSED AND SPIRO COUMARINS: COUMARIN-3-THIOCARBOXAMIDE AS BUILDING BLOCK FOR THE SYNTHESIS OF CONDENSED AND SPIRO COUMARINS

  摘要：

  Coumarin-3-thiocarboxamide 1 was reacted with malononitrile, cyanoacetamide or cyanothioacetamide to give the corresponding thiopyrano(3,4-c)coumarin-1-carbonitrile 2. Also, compound 1 was reacted with a variety of active methylenes having an alpha-cyano or alpha-keto group to give thiopyranocoumarin derivatives 3-9. The reaction of compound 1 with different ketene N,S-acetals, afforded the corresponding thiazino(5,4c)coumarin derivatives 10,13 and 16. On reacting compound 10 or 13 with malononitrile, spiro pyran-4,2'-thiazino(5,4-c)coumarin 11 or 14 were obtained, while the reaction of compound 16 with malononitrile gave spiro cyclobutene-1,2'-thiazino(5,4-c)coumarin derivative 17. Treating of compounds 10, 13 or 16 with cyclohexylidenemalononitrile afforded spiro naphthyl-1,2'-tkiazino(5,4-c) coumarin derivatives 12,15 or 18 respectively. Treatment of compound I with CS2 and malononitrile under PTC condition afforded 1,3-dithiano(5,4-c) coumarin derivative 19, which in turn reacted with malononitrile or cyclohexylidenemalononitrile to afford spiro cyclobut-2-enyl-1,2'-(1,3)dithiano(5,4-c)coumarin 20 and spiro naphthyl-1,'2-(1,3)dithiano(5,4-c)coumarin 21 derivatives, respectively.

  DOI：

  10.1080/10426500008043675
• 作为产物：
  描述：

  3-[双(甲基磺酰基)亚甲基]-2,4-戊二酮 、 苯胺 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 3-acetyl-4-methylthio-4-phenylaminobut-3-en-2-one
  参考文献：
  名称：

  ZnCl 2催化[4 + 1]烷硫基取代的烯胺酮和烯胺硫酮与硫叶立德的环化。

  摘要：

  呋喃和噻吩单元的简洁结构在潜在生物活性化合物和功能材料的合成中发挥了重要作用。在本文中，我们报告了一种有效的路易斯酸ZnCl 2催化的烷硫基取代的烯胺酮（即α-氧代烯酮N，S-乙缩醛）与硫的酰基化物的[4 + 1]环化反应，得到2-酰基-3-氨基呋喃衍生物。以类似的方式，相应的烯氨基噻酮，即α-硫代乙烯酮N，S-乙缩醛与硫酰化物的[4 + 1]环化有效地产生了多取代的3-氨基噻吩。该方法具有广泛的底物范围和宽泛的官能团耐受性，为获得高度官能化的呋喃和噻吩提供了一条简洁的途径。

  DOI：

  10.1002/chem.201905483

文献信息

• SYNTHESIS OF FUSED AND SPIRO HETEROCYCLIC COMPOUNDS DERIVED FROM 3,5-PYRAZOLIDINEDIONE DERIVATIVES
  作者：A. Khodairy

  DOI：10.1080/10426500008043678

  日期：2000.5.1

  Abstract The reaction of compound 1 with triethyl orthoformate afforded 2, which in turn reacted with CS2 and active methlyene compounds or malononitrile to give dithiolane and 4-malononitrile methylene derivatives 3,4, respectively. Treatment of compound 4 with active methylene compounds afforded spiro cyclopentene derivatives 5a-c. Compound 1 was reacted with bromomalononitrile or CS2 and halocompounds

  摘要 化合物1与原甲酸三乙酯反应得到2，后者再与CS2和活性亚甲基化合物或丙二腈反应，分别得到二硫戊环和4-丙二腈亚甲基衍生物3,4。用活性亚甲基化合物处理化合物4得到螺环戊烯衍生物5a-c。化合物 1 与溴丙二腈或 CS2 和卤代化合物反应得到呋喃。噻吩基和二硫基戊基吡唑衍生物分别为 6-11。化合物 12 与苯甲酰溴或亚苄基丙二腈的反应分别提供 oxathiol-2-ylidene 和吡啶硫酮衍生物 13,14。二溴衍生物16与CS2和活性亚甲基或丙二腈反应，分别得到螺二噻烷17a-e和4-二氰基-亚甲基衍生物22。化合物 17 与巯基乙酸、N-苯基苯并肼基溴、2,5-二甲基呋喃和 1-苯基-3,5-吡唑烷二 1 进行环加成反应，分别得到环加合物 18-21。用二氰基化合物 22 处理 > 邻氨基苯硫酚或邻苯二胺导致形成螺硫氮杂或螺二嗪衍生物 23a,b。亚芳基衍生物 24 与 S,S-缩醛、N
• A FACILE METHOD FOR THE SYNTHESIS OF NOVEL PYRIDINONE DERIVATIVES VIA KETENE<i>N</i>,<i>S</i>-ACETALS
  作者：Eljazi I. Al-Afaleq

  DOI：10.1081/scc-100106218

  日期：2001.1

  A simple and easy method is provided for the synthesis of the novel pyridinone derivatives (3a-e), (8a-c) and (10a-c) by the reaction of ketene acetals (2a-e), (7a-c) and (9a-c) with ethyl cyanoacetate respectively. Compounds (3b-d) reacted with triethyl orthoformate to afford the pyridinone derivatives (4-6) respectively. Compound 7a reacted with ethyl acetoacetate or diethyl malonate to give thiazolopyridinone derivative 11 or 12 respectively.
• NEW SYNTHETIC APPROACHES TO CONDENSED AND SPIRO COUMARINS: COUMARIN-3-THIOCARBOXAMIDE AS BUILDING BLOCK FOR THE SYNTHESIS OF CONDENSED AND SPIRO COUMARINS
  作者：A. M.M. El-Saghier、A. Khodairy

  DOI：10.1080/10426500008043675

  日期：2000.5.1

  Coumarin-3-thiocarboxamide 1 was reacted with malononitrile, cyanoacetamide or cyanothioacetamide to give the corresponding thiopyrano(3,4-c)coumarin-1-carbonitrile 2. Also, compound 1 was reacted with a variety of active methylenes having an alpha-cyano or alpha-keto group to give thiopyranocoumarin derivatives 3-9. The reaction of compound 1 with different ketene N,S-acetals, afforded the corresponding thiazino(5,4c)coumarin derivatives 10,13 and 16. On reacting compound 10 or 13 with malononitrile, spiro pyran-4,2'-thiazino(5,4-c)coumarin 11 or 14 were obtained, while the reaction of compound 16 with malononitrile gave spiro cyclobutene-1,2'-thiazino(5,4-c)coumarin derivative 17. Treating of compounds 10, 13 or 16 with cyclohexylidenemalononitrile afforded spiro naphthyl-1,2'-tkiazino(5,4-c) coumarin derivatives 12,15 or 18 respectively. Treatment of compound I with CS2 and malononitrile under PTC condition afforded 1,3-dithiano(5,4-c) coumarin derivative 19, which in turn reacted with malononitrile or cyclohexylidenemalononitrile to afford spiro cyclobut-2-enyl-1,2'-(1,3)dithiano(5,4-c)coumarin 20 and spiro naphthyl-1,'2-(1,3)dithiano(5,4-c)coumarin 21 derivatives, respectively.
• ZnCl ₂ ‐Catalyzed [4+1] Annulation of Alkylthio‐Substituted Enaminones and Enaminothiones with Sulfur Ylides
  作者：Yuan He、Jiang Lou、Zhengkun Yu、Yong‐Gui Zhou

  DOI：10.1002/chem.201905483

  日期：2020.4.16

  in the synthesis of potentially bioactive compounds and functional materials. Herein, we report an efficient Lewis acid ZnCl 2 -catalyzed [4+1] annulation of alkylthio-substituted enami-nones, that is, α -oxo ketene N,S -acetals, with sulfur ylides, affording 2-acyl-3-aminofuran derivatives. In a similar fashion, [4+1] annulation of the corresponding enaminothiones, that is, α -thioxo ketene N,S -acetals

  呋喃和噻吩单元的简洁结构在潜在生物活性化合物和功能材料的合成中发挥了重要作用。在本文中，我们报告了一种有效的路易斯酸ZnCl 2催化的烷硫基取代的烯胺酮（即α-氧代烯酮N，S-乙缩醛）与硫的酰基化物的[4 + 1]环化反应，得到2-酰基-3-氨基呋喃衍生物。以类似的方式，相应的烯氨基噻酮，即α-硫代乙烯酮N，S-乙缩醛与硫酰化物的[4 + 1]环化有效地产生了多取代的3-氨基噻吩。该方法具有广泛的底物范围和宽泛的官能团耐受性，为获得高度官能化的呋喃和噻吩提供了一条简洁的途径。