N-(3-oxo-1-phenylbut-1-en-1-yl)-2-chloroacetamide | 1607833-71-5

• 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: N-(3-oxo-1-phenylbut-1-en-1-yl)-2-chloroacetamide
• 英文别名: N-(4-oxo-4-phenylbut-2-en-2-yl)-2-chloroacetamide
• CAS: 1607833-71-5
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: GBIVGNKEAMBZSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(3-oxo-1-phenylbut-1-en-1-yl)-2-chloroacetamide 在 一水合肼 作用下， 以 水 、 正丁醇 为溶剂， 反应 3.0h， 生成 3-amino-6-methyl-4-phenylpyridin-2(1H)-one
  参考文献：
  名称：

  Synthesis of 3-Aminopyridin-2(1H)-Ones and 1H-Pyrido[2,3-b][1,4]Oxazin-2(3H)-Ones

  摘要：

  The interaction of 1,3-diketones with chloroacetamide produced N-(3-oxoalkenyl)chloroacetamides. Heating of N-(3-oxoalkenyl)chloroacetamides with an excess of pyridine in ethanol or butanol led to the formation of pyridin-2(1De)-ones, substituted with a pyridine ring at position 3. The reactions of these compounds with hydrazine hydrate produced 3-aminopyridin-2(1De)-ones. The synthesis of 1H-pyrido[2,3-b][1, 4]oxazin-2(3H)-ones was accomplished by a reaction of 3-aminopyridin-2(1De)-ones with chloroacetyl chloride.

  DOI：

  10.1007/s10593-014-1464-9
• 作为产物：
  描述：

  1-苯基-1,3-丁二酮 在 吡啶 、 ammonium acetate 作用下， 以 氯仿 、 苯 为溶剂， 生成 N-(3-oxo-1-phenylbut-1-en-1-yl)-2-chloroacetamide
  参考文献：
  名称：

  Synthesis of 3-Aminopyridin-2(1H)-Ones and 1H-Pyrido[2,3-b][1,4]Oxazin-2(3H)-Ones

  摘要：

  The interaction of 1,3-diketones with chloroacetamide produced N-(3-oxoalkenyl)chloroacetamides. Heating of N-(3-oxoalkenyl)chloroacetamides with an excess of pyridine in ethanol or butanol led to the formation of pyridin-2(1De)-ones, substituted with a pyridine ring at position 3. The reactions of these compounds with hydrazine hydrate produced 3-aminopyridin-2(1De)-ones. The synthesis of 1H-pyrido[2,3-b][1, 4]oxazin-2(3H)-ones was accomplished by a reaction of 3-aminopyridin-2(1De)-ones with chloroacetyl chloride.

  DOI：

  10.1007/s10593-014-1464-9

文献信息

• Reaction of N-(3-oxoalkenyl)chloroacetamides with sodium p-toluenesulfinate – synthesis of 3-tosylpyridin-2(1Н)-ones
  作者：Dmitry S. Goncharov、Ivan V. Kulakov、Alexander S. Fisyuk

  DOI：10.1007/s10593-018-2215-0

  日期：2017.12

  A series of N-(3-oxoalkenyl)chloroacetamides was prepared by acylation of β-enaminoketones with chloroacetyl chloride. A reaction of these compounds with sodium p-toluenesulfinate in dimethylformamide in the presence of potassium carbonate led to 3-tosylpyridin-2(1H)-ones. The limitations of this reaction were studied.

  通过用氯乙酰氯将β-烯酮酮酰化来制备一系列N-（3-氧代烯基）氯乙酰胺。在碳酸钾存在下，这些化合物与对甲苯磺酸钠在二甲基甲酰胺中的反应生成3-甲苯磺酰吡啶-2（1 H）-one 。研究了该反应的局限性。
• Intramolecular cyclization of 2-(heteroarylsulfanyl)-N-(3-oxoalkenyl)acetamides: synthesis of 3-(heteroarylsulfanyl)- and 3-sulfanylpyridin-2(1H)-ones
  作者：Olga А. Savchenko、Vera V. Musiyak、Dmitry S. Goncharov、Yulia P. Bogza、Anton L. Shatsauskas、Valentin P. Talzi、Sergey N. Evdokimov、Evgeny B. Ulyankin、Alexander S. Fisyuk

  DOI：10.1007/s10593-020-02795-1

  日期：2020.9

  The reaction of 2-chloro-N-(3-oxoalkenyl)acetamides with 1,3-benzothiazole-2(3H)-thione, 1,3-benzoxazole-2(3H)-thione, and 1-methyl-1,3-dihydro-2H-benzimidazole-2-thione led to the formation of 2-(heteroarylsulfanyl)-N-(3-oxoalkenyl)acetamides. By the action of a base, these compounds were converted into pyridin-2(1H)-ones containing a divalent sulfur atom in position C-3 bonded to a heterocyclic ring

  2-氯-N-（3-氧代烯基）乙酰胺与1,3-苯并噻唑-2（3 H）-硫酮，1,3-苯并恶唑-2（3 H）-硫酮和1-甲基-1的反应，3-二氢-2 H-苯并咪唑-2-硫酮导致形成2-（杂芳基硫烷基）-N-（3-氧代烯基）乙酰胺。在碱的作用下，这些化合物被转化为在与杂环键合的C-3位上含有二价硫原子的吡啶-2（1 H）-1 。已经研究了3-（1,3-苯并噻唑-2-基硫烷基）吡啶-2（1 H）-一的溴化，硝化和烷基化。锌在乙酸中的作用将这些化合物转化为3-硫烷基吡啶2-2（1 H）-one。