4-[(3-cyano-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)thio]-3-oxobutanoic acid ethyl ester | 290299-61-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-[(3-cyano-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)thio]-3-oxobutanoic acid ethyl ester
• 英文别名: ethyl 4-[(3-cyano-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)sulfanyl]-3-oxobutanoate
• CAS: 290299-61-5
• 化学式: C₁₅H₁₆N₂O₃S
• mdl: MFCD00742455
• 分子量: 304.37
• InChiKey: HVLNOCYDURSSHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  438.5±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[(3-cyano-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)thio]-3-oxobutanoic acid ethyl ester 在 氢氧化钾 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.41h， 生成 6-Hydroxy-8-thia-3,10-diazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(9),2(7),5,10,15-pentaen-4-one
  参考文献：
  名称：

  Synthesis of substituted 4-hydroxy-1H-thieno[2,3-b;4,5-b′]dipyridin-2-ones

  摘要：

  Substituted 4-hydroxy-1 H-thieno[2,3-b;4,5-b']dipyridin-2-ones were prepared by the reactions of 3-cyanopyridine-2(1 H)-thiones with alkyl 4-chloroacetoacetates and by intramolecular cyclization of alkyl 4-(2-pyridylthio)acetoacetates or alkyl 3-(3-aminothieno[2,3-b]pyridin-2-yl)-3-oxopropionates under the action of bases.

  DOI：

  10.1007/bf02494687
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 、 2-thioxo-2,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitrile 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以84%的产率得到4-[(3-cyano-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)thio]-3-oxobutanoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of substituted 4-hydroxy-1H-thieno[2,3-b;4,5-b′]dipyridin-2-ones

  摘要：

  Substituted 4-hydroxy-1 H-thieno[2,3-b;4,5-b']dipyridin-2-ones were prepared by the reactions of 3-cyanopyridine-2(1 H)-thiones with alkyl 4-chloroacetoacetates and by intramolecular cyclization of alkyl 4-(2-pyridylthio)acetoacetates or alkyl 3-(3-aminothieno[2,3-b]pyridin-2-yl)-3-oxopropionates under the action of bases.

  DOI：

  10.1007/bf02494687

文献信息

• 4-(3-Cyanopyridin-2-ylthio)acetoacetates in synthesis of heterocycles
  作者：L. A. Rodinovskaya、A. M. Shestopalov、A. V. Gromova

  DOI：10.1023/b:rucb.0000011877.60574.34

  日期：2003.10

  Substituted 2-amino-4-aryl-3-cyano-5-oxo-5,6-dihydro-4H-pyrano[2,3-d]pyrido[3",2":4,5]thieno[3,2-b]pyridines were synthesized by the reactions of 4-hydroxy-1H-thieno[2,3-b;4,5-b]dipyridin-2-ones with arylidenemalononitriles or by the three-component reactions of hydroxythienodipyridinones with aldehydes and malononitrile in DMF in the presence of triethylamine. Methods for syntheses of substituted

  取代的 2-amino-4-aryl-3-cyano-5-oxo-5,6-dihydro-4H-pyrano[2,3-d]pyrido[3",2":4,5]thieno[3,2 -b]吡啶是通过 4-羟基-1H-噻吩并[2,3-b;4,5-b]二吡啶-2-酮与亚芳基丙二腈的反应或羟基噻吩二吡啶酮与醛和丙二腈的三组分反应合成的在三乙胺存在下的 DMF 中。在4-(3-cyanopyridin-2-)反应的基础上,开发了取代3-烷氧基羰基-6-氨基-4-芳基-2-(3-氰基吡啶-2-基硫甲基)-4H-吡喃的合成方法。硫代)乙酰乙酸酯和亚芳基丙二腈或醛和丙二腈。4-(3-氰基吡啶-2-基硫基)乙酰乙酸乙酯和4-甲氧基亚苄基氰基硫代乙酰胺用于合成6-(吡啶-2-基硫甲基)-3-氰基吡啶-2(1H)-硫酮。
• Substituted 4-(3-Cyanopyridin-2-ylthio)acetoacetates: New Convenient Reagents for the Synthesis of Heterocycles
  作者：Lyudmila Rodinovskaya、Anatoliy Shestopalov、Anna Gromova、Alexander Shestopalov

  DOI：10.1055/s-2006-942433

  日期：——

  Polyfunctional 4-(3-cyanopyridin-2-ylthio)acetoacetates were used in the synthesis of 4-hydroxy-1H-thieno[2,3-b:4,5-b]dipyridin-2-ones. The latter were used in reactions with arylidene-malononitriles or in three-component reactions with aldehydes and malononitrile to give 2-amino-4-aryl-3-cyano-5-oxo-5,6-dihydro-4H-pyrano[2,3-d]pyrido[3',2':4,5]thieno[3,2-b]pyridines. Utilizing 4-(3-cyanopyridin-2

  多官能团 4-(3-cyanopyridin-2-ylthio)acetoacetates 用于合成 4-hydroxy-1H-thieno[2,3-b:4,5-b]dipyridin-2-ones。后者用于与亚芳基-丙二腈的反应或与醛和丙二腈的三组分反应，得到 2-amino-4-aryl-3-cyano-5-oxo-5,6-dihydro-4H-pyrano[2, 3-d]吡啶并[3',2':4,5]噻吩并[3,2-b]吡啶。利用 4-(3-cyanopyridin-2-ylthio)acetoacetates 和亚芳基丙二腈或醛和丙二腈，我们开发了一种合成取代的 3-alkoxycarbonyl-6-amino-4-aryl-2-(3-cyanopyridin-2-基硫甲基）-4H-吡喃。取代的 4-(3-cyanopyridin-2-ylthio)acetoacetates 与水合肼反应生成取代的
• Synthesis of substituted 4-hydroxy-1H-thieno[2,3-b;4,5-b′]dipyridin-2-ones
  作者：L. A. Rodinovskaya、A. M. Shestopalov

  DOI：10.1007/bf02494687

  日期：2000.2

  Substituted 4-hydroxy-1 H-thieno[2,3-b;4,5-b']dipyridin-2-ones were prepared by the reactions of 3-cyanopyridine-2(1 H)-thiones with alkyl 4-chloroacetoacetates and by intramolecular cyclization of alkyl 4-(2-pyridylthio)acetoacetates or alkyl 3-(3-aminothieno[2,3-b]pyridin-2-yl)-3-oxopropionates under the action of bases.