6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidin-4(1H)-one | 119730-48-2

• 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: 6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidin-4(1H)-one
• 英文别名: 6-methyl-2-phenacylidene-1H-pyrimidin-4-one
• CAS: 119730-48-2
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: LWCMJABJPRWSCY-UHFFFAOYSA-N

物化性质

• 熔点：
  247-250 °C(Solv: ethanol (64-17-5))
• 沸点：
  427.2±45.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidin-4(1H)-one 在 盐酸羟胺 、 potassium hydroxide 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.5h， 生成 2-(1,2-dihydroxyimino-2-phenylethyl)-6-methylpyrimidin-4(3H)-one
  参考文献：
  名称：

  Reaction of 6-methyl-2-(2-oxo-2-phenyl-ethylidene)-2,3-dihydropyrimidin-4(1H)-one with hydrazine and hydroxylamine

  摘要：

  The reaction of 6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidin-4(1H)-one and of its nitrosation product with hydroxylamine stops at the stage of forming the corresponding oximes. The reaction of 6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidin-4(1H)-one with hydrazine yields a mixture of 3-amino-5-phenylpyrazole and 3-methyl-2-pyrazolin-5-one in 71 and 62% yields, respectively. The ketoxime is used in the synthesis of a series of imidazole N(3)-oxides substituted at the 1, 4, and 5 positions of the imidazole ring.

  DOI：

  10.1007/s10593-013-1162-z
• 作为产物：
  描述：

  alpha-氯乙酰苯 在 sodium hydroxide 作用下， 以 二苯醚 、 乙醇 为溶剂， 反应 0.33h， 生成 6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidin-4(1H)-one
  参考文献：
  名称：

  Hurst, Derek T.; Beaumont, Claire; Jones, Derek T. E., Australian Journal of Chemistry, 1988, vol. 41, # 8, p. 1209 - 1219

  摘要：

  DOI：

文献信息

• Reaction of 2-(2-oxo-2-arylethylidene)-2,3-dihydropyrimidine-4(1H)-ones with aldehydes
  作者：A. A. Yavolovskii、L. V. Grishchuk、E. I. Bevzyuk、Yu. E. Ivanov、D. E. Stepanov、S. M. Pluzhnik-Gladyr、G. L. Kamalov

  DOI：10.1134/s1070363214050156

  日期：2014.5

  3-dihydropyrimidine-4(1H)-ones react with aromatic and heteroaromatic aldehydes to form the unsaturated ketones, whereas in the case of 3- and 4-benzaldehydes the corresponding trans-2-styrylpyrimidine-4(3H)-ones were obtained. A possible mechanism of hydrolytic cleavage of the product of condensation of 2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidine-4(1H)-one with paraformaldehyde under acid catalysis and mechanochemical

  2-（2-氧-2-芳基亚乙基）-2,3-二氢嘧啶-4（1H）-与芳族和杂芳族醛反应形成不饱和酮，而在3-和4-苯甲醛的情况下，相应的反式获得了-2-苯乙烯基嘧啶-4（3H）-1 。讨论了2-（2-氧代-2-苯基亚乙基）-2,3-二氢嘧啶-4（1H）-与多聚甲醛在酸催化和机械化学活化作用下发生水解裂解的可能机理。
• Synthesis of 6-methyl-2-[2-phenyl-2-(arylhydrazono)ethyl]-3Н-pyrimidine-4-ones and their oxidation by hydrogen peroxide and selenium dioxide
  作者：A. A. Yavolovskii、S. M. Pluzhnik-Gladyr、Yu. E. Ivanov、D. E. Stepanov、L. V. Grishchuk、G. L. Kamalov

  DOI：10.1134/s1070363216070112

  日期：2016.7

  arylhydrazines leads in high yields to the corresponding hydrazones, in which the ethylidene fragment of the starting compound is transformed to the ethylene fragment. By oxidation of the hydrazones with hydrogen peroxide or selenium dioxide the corresponding 6-methyl-2-[2-phenyl-2-(arylhydrazono)acetyl]-3H-pyrimidine-4-ones were synthesized.

  6-甲基-2-（2-氧代-2-苯基亚乙基）-2,3-二氢嘧啶-4（1 H）-one与芳基肼的反应可高产率地得到相应的，其中the的亚乙基片段起始化合物转化为乙烯片段。通过与过氧化氢或二氧化硒相应的6-甲基-2-腙的氧化[2-苯基-2-（芳基亚肼基）乙酰基] -3 ħ -嘧啶-4-酮合成。
• Peculiarities of cyclization of 2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidin-4(1Н)-one with ethyl cyanoacetate
  作者：Arkadii А. Yavolovskii、Lidiya V. Grishchuk、Sergei M. Pluzhnik-Gladyr、Yurii E. Ivanov、Ildar M. Rakipov、Dmitrii E. Stepanov、Gerbert L. Kamalov

  DOI：10.1007/s10593-019-02480-y

  日期：2019.5

  The reaction of 2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidin-4(1H)-ones and ethyl cyanoacetate leads to the formation of 4-hydroxy-2,10-dioxo-5-phenyl-1,10-dihydro-2H-pyrimido[1,2-a][1,8]naphthyridine-3-carbonitriles.

  2-（2-氧代-2-苯基亚乙基）-2,3-二氢嘧啶-4（1 H）-与氰基乙酸乙酯的反应导致形成4-羟基-2,10-二氧代-5-苯基- 1,10-二氢-2 H-嘧啶基[1,2- a ] [1,8]萘啶-3-甲腈。
• Reaction of 1,4-Benzoquinone with 2-(2-Oxo-2-arylethylidene)-2,3-dihydropyrimidine-4(1H)-ones
  作者：A. А. Yavolovskii、L. V. Grishchuk、S. M. Pluzhnik-Gladyr、D. E. Stepanov、Yu. E. Ivanov、G. L. Kamalov

  DOI：10.1134/s1070363220060250

  日期：2020.6

  AbstractReactions of 1,4-benzoquinone with 2-(2-oxo-2-arylethylidene)-2,3-dihydro-1H-pyrimidine-4-ones in glacial acetic acid proceed selectively to give 2-[1-(2,5-dihydrophenyl)-2-oxo-2-arylethylidene]-2,3-dihydropyrimidine-4(1H)-ones.

  摘要1,4-苯醌与2-（2-氧代-2-芳基亚乙基）-2,3-二氢-1 H-嘧啶-4-酮在冰醋酸中的反应选择性进行，得到2- [1-（2， 5-二氢苯基）-2-氧代-2-芳基亚乙基] -2，3-二氢嘧啶-4（1 H）-ones。
• Synthesis of pyridinylketones, and their cyclic derivatives produced from 6-methyl-2-thiouracil
  作者：A. A. Yavolovskii、L. V. Grishchuk、I. M. Rakipov、Yu. E. Ivanov、D. E. Stepanov、G. L. Kamalov

  DOI：10.1134/s1070363212040196

  日期：2012.4

  A possibility to obtain pyrimidines, containing oxoalkyl moiety in 2 position of the ring from the available 6-methyl-2-thiouracil was shown.