2,4-戊二酮,3-[氨基(乙硫基)亚甲基]- | 139057-00-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 中文名称: 2,4-戊二酮,3-[氨基(乙硫基)亚甲基]-
• 英文名称: 3-<(ethylthio)aminomethylene>pentane-2,4-dione
• 英文别名: 3-[amino(ethylsulfanyl)methylidene]pentane-2,4-dione
• CAS: 139057-00-4
• 化学式: C₈H₁₃NO₂S
• 分子量: 187.263
• InChiKey: RJUAAWMRBARVSI-UHFFFAOYSA-N

物化性质

• 沸点：
  341.0±42.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.16
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,4-戊二酮,3-[氨基(乙硫基)亚甲基]- 在 cobalt(II) acetate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以87%的产率得到1-amino-1-ethylthiobut-1-en-3-one
  参考文献：
  名称：

  Synthesis of the N,S-acetals of diacyl- and alkoxycarbonyl(acyl)ketenes with ?-dicarbonyl compounds, organic thiocyanates, and nickel(2+) complexes

  摘要：

  An effective method is proposed for the production of the N,S-acetals of diacylketenes and acyl(alkoxycarbonyl)ketenes, based on the addition of methylene-active beta-diketones and beta-ketoesters to alkyl and aryl thiocyanates catalyzed by Ni(2+) acetylacetonate. Methods are indicated for the synthetic utilization of diacetylketene N,S-acetals and include their conversion to ketene aminals, chelation with boron compounds, and deacylation of derivatives of monoacetylketene with methanol in the presence of Co(2+) acetate.

  DOI：

  10.1007/bf00961051
• 作为产物：
  描述：

  硫氰酸乙酯 、 乙酰丙酮 在 bis(acetylacetonate)nickel(II) 作用下， 以61%的产率得到2,4-戊二酮,3-[氨基(乙硫基)亚甲基]-
  参考文献：
  名称：

  Synthesis of the N,S-acetals of diacyl- and alkoxycarbonyl(acyl)ketenes with ?-dicarbonyl compounds, organic thiocyanates, and nickel(2+) complexes

  摘要：

  An effective method is proposed for the production of the N,S-acetals of diacylketenes and acyl(alkoxycarbonyl)ketenes, based on the addition of methylene-active beta-diketones and beta-ketoesters to alkyl and aryl thiocyanates catalyzed by Ni(2+) acetylacetonate. Methods are indicated for the synthetic utilization of diacetylketene N,S-acetals and include their conversion to ketene aminals, chelation with boron compounds, and deacylation of derivatives of monoacetylketene with methanol in the presence of Co(2+) acetate.

  DOI：

  10.1007/bf00961051

文献信息

• Synthesis of new 5-hydroxyquinazoline derivatives from functionalized 5-acetyl-6-methylpyrimidines
  作者：Alexander V. Komkov、Mikhail A. Kozlov、Yurii A. Linitskii、Leonid S. Vasil’ev、Andrey S. Dmitrenok、Igor V. Zavarzin

  DOI：10.1007/s10593-021-02981-9

  日期：2021.8

  A new method for the synthesis of quinazolines based on the annulation of the benzene ring to 5-acetyl-6 methylpyrimidin-2-one(thione) derivatives has been proposed. Condensation of the latter at the methyl group with dimethylformamide dimethyl acetal in boiling PhH leads to the formation of 5-acetyl-6-[2-(dimethylamino)vinyl]pyrimidin-2-ones(thiones), which, when boiled with MeONa in MeOH, cyclize

  提出了一种基于苯环环化为 5-乙酰基-6 甲基嘧啶-2-酮（硫酮）衍生物合成喹唑啉的新方法。后者在沸腾的 PhH 中与二甲基甲酰胺二甲基缩醛在甲基上的缩合导致形成 5-乙酰基-6-[2-（二甲氨基）乙烯基]嘧啶-2-酮（硫酮），当与 MeONa 一起煮沸时， MeOH，环化为 5-羟基喹唑啉-2-酮（硫酮）。类似地，5-乙酰基-6-甲基-4-(三氟甲基)嘧啶转化为5-羟基-4-(三氟甲基)喹唑啉。喹唑啉不是由 5-乙酰基-6-甲基嘧啶与二甲基甲酰胺二甲基缩醛在乙酰基上缩合而成，但 5-乙酰基-6-甲基嘧啶可用于获得吡啶并[2,3- d ]嘧啶衍生物。
• Synthesis of derivatives of 4-alkylthiouracil, cytosine, pyrido[2,3-d]pyrimidine, and pyrimido[4,5-d]pyrimidine from the N,S- and N,N-acetals of diacetylketene and isocyanates
  作者：V. A. Dorokhov、M. F. Gordeev、A. V. Komkov、V. S. Bogdanov

  DOI：10.1007/bf00961050

  日期：1991.11

  The action of alkyl and aryl isocyanates on the N,S-acetals of diacetylketene leads to the formation of 4-alkylthio-5-acetyl-1-alkyl(aryl)-6-methyl-1H-pyrimidin-2-ones (derivatives of 4-alkylthiouracils). The reaction of the synthesized thiouracils with amines or the reaction of the N,N-acetals of diacetylketene (N,N-ADK) with an equimolar amount of aryl isocyanates leads to the formation of substituted 4-amino-5-acetyl-1H-pyrimidin-2-ones derivatives of cytosine). From the latter and isocyanates or directly from N,N-ADK and an excess of the isocyanate, derivatives of 4-methylene-1H,3H,4H-pyrimido[4,5-d]pyrimidine-2,7-dione were obtained. The exception was the condensation of 3-[N-(4,6-dimethyl-2-pyrimidinyl)diaminomethylene]pentane-2,4-dione with aryl isocyanates, which led to 3H,8H-pyrido[2,3-d]pyrimidine-2,5-diones.