1-(4-methylphenyl)-3,4,4-trichloro-3-buten-1-one | 515159-59-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-methylphenyl)-3,4,4-trichloro-3-buten-1-one
• 英文别名: 3,4,4-trichloro-1-(4-methylphenyl)-3-buten-1-one；3,4,4-trichloro-1-(4-methylphenyl)but-3-en-1-one；3-Buten-1-one, 3,4,4-trichloro-1-(4-methylphenyl)-
• CAS: 515159-59-8
• 化学式: C₁₁H₉Cl₃O
• 分子量: 263.551
• InChiKey: ZOZDGQZLQYLOMU-UHFFFAOYSA-N

物化性质

• 熔点：
  68-69 °C
• 沸点：
  381.9±42.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-methylphenyl)-3,4,4-trichloro-3-buten-1-one 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 以96%的产率得到2-溴-3,4,4-三氯-1-(4-甲基苯基)丁-3-烯-1-酮
  参考文献：
  名称：

  Synthesis of 3,4-dibromo-3,4,4-trichloro-1-phenylbutan-1-one and 1-aryl-2-bromo-3,4,4-trichlorobut-3-en-1-ones from 3,4,4-trichlorobut-3-enoic acid

  摘要：

  Bromination of 3,4,4-trichlorobut-3-enoic acid in boiling carbon tetrachloride led to the formation of 2-bromo-3,4,4-trichlorobut-3-enoic acid as a result of replacement of hydrogen in the CH2 group. The reaction at 40 degrees C involved the double C=C bond to give 3,4-dibromo-3,4,4-trichlorobutanoic acid. The brominated acids were converted into the corresponding chlorides which were used to acylate benzene, toluene, and bromobenzene according to Friedel-Crafts. The acylation was not selective, and only the reaction of 3,4-dibromo-3,4,4-trichlorobutanoyl chloride with benzene gave 3,4-dibromo-3,4,4-trichloro-1-phenylbutan-1-one as the only product. 1-Aryl-2-bromo-3,4,4-trichlorobut-3-en-1-ones were synthesized by bromination of the corresponding 1-aryl-3,4,4-trichlorobut-3-en-1-ones which were prepared previously by Friedel-Crafts acylation of substituted benzenes with 3,4,4-trichlorobut-3-enoyl chloride.

  DOI：

  10.1134/s107042800711005x
• 作为产物：
  描述：

  甲苯 、 3,4,4-trichloro-3-butenoyl chloride 在 三氯化铝 作用下， 以71%的产率得到1-(4-methylphenyl)-3,4,4-trichloro-3-buten-1-one
  参考文献：
  名称：

  摘要：

  From 3,4,4-trichloro-3-butenoic acid 3,3,4,4,4-pentachlorobutanoic, 3,4,4,4-tetrachloro-2-butenoic, and 2,3,4,4-tetrachloro-3-butenoic acids were synthesized. By Friedel-Krafts reaction from 3,4,4-trichloro-3-butenoyl and 3,3,4,4,4-pentachlorobutanoyl chlorides with aromatic hydrocarbons the corresponding aryl chloroalkyl ketones were prepared. It was established that dehydrochlorination of 2,2,3,3,3-pentachloropropyl phenyl ketone with aqueous alkali under conditions of the phase-transfer catalysis at the molar ratio of reagents ketone: KOH: triethylbenzylammoniurn chloride equal to 1: 4: 0.05 involved the cleavage of two HCl molecules and resulted in 3,3,3-trichloro-1-propynyl phenyl ketone.

  DOI：

  10.1023/a:1020980921916

文献信息

• Synthesis of functional derivatives of aryl trichlorovinyl (trichloroallyl) ketones via consecutive transformations of the carbonyl group
  作者：V. I. Potkin、S. K. Petkevich、A. V. Kletskov、E. A. Dikusar、I. B. Rozentsveig、G. G. Levkovskaya

  DOI：10.1134/s1070428014100042

  日期：2014.10

  An efficient procedure have been developed for the selective reduction of the carbonyl group in phenyl trichlorovinyl ketone and aryl trichloroallyl ketones by the action of NaBH4 in propan-2-ol to obtain the corresponding alcohols. The hydroxy group in the latter was converted into amino by the Ritter reaction. Treatment of the alcohols and amines with 5-phenylisoxazole-3-carbonyl chloride and 4,5-dichloroisothiazole-3-carbonyl chloride gave the corresponding esters and amides, and condensation of the amines with aromatic aldehydes afforded Schiff bases.
• Synthesis of 3-aryl-5-dichloromethyl-1H-pyrazole-1-carboxamides from 1-aryl-3,4,4-trichlorobut-3-en-1-ones
  作者：S. K. Petkevich、V. I. Potkin、R. V. Kaberdin

  DOI：10.1134/s1070428006100149

  日期：2006.10

  The reaction of 1-aryl-3,4,4-trichlorobut-3-en-1-ones with semicarbazide hydrochloride in the presence of sodium acetate is accompanied by prototropic allylic rearrangement, leading to the formation of two isomeric products, semicarbazones of the initial ketones and 1-aryl-3,4,4-trichlorobut-2-en-1-one semicarbazones. The latter undergo heterocyclization in the presence of triethylamine to give the corresponding 3-aryl-5-dichloromethyl-1H-pyrazole-1-carboxamides.
• Synthesis of Sybstituted Isoxazoles and Pyrazoles Based on 1-Aryl-3,4,4-trichloro-3-buten-1-ones
  作者：S. K. Petkevich、V. I. Potkin、R.V. Kaberdin

  DOI：10.1023/b:rujo.0000045896.42146.ad

  日期：2004.8

  3-Aryl-5-methylenehydroxyiminoisoxazoles were synthesized by reaction of 1-aryl-3,4,4-trichloro-3-buten-1- ones with hydroxylamine. Reactions of ketones with hydrazine provided pyrazole structures; therewith two pyrazole molecules underwent "coupling" affording 3-arylpyrazole-5-carbaldehyde azines.
• ——
  作者：V. I. Potkin、S. K. Petkevich、R. V. Kaberdin、L. Yu. Tychinskaya

  DOI：10.1023/a:1021695527813

  日期：——

  Reaction of 3,4,4-trichloro-1-(4-methylphenyl)-3-buten-1-one with amines results in replacement of the internal chlorine atom and is accompanied by prototropic allyl rearrangement leading to formation of the corresponding 3-amino-4,4-dichloro-1-(4-methylphenyl)-2-buten-1-ones. The reaction of the title compound with 2,4-dinitrophenylhydrazine yields 3,4,4-trichloro-1-(4-methylphenyl)-3-buten-1-one 2,4-dinitrophenylhydrazone and is not accompanied by allyl rearrangement.
• Bimolecular Condensation of 1-(para-tolyl)-and 1-(biphenyl-4-yl)-3,4,4-trichloro-3-buten-1-ones to 2,3,4,6-substituted 4Н-pyrans*
  作者：V. I. Potkin、S. K. Petkevich、P. V. Kurman、G. G. Levkovskaya、L. S. Ivashkevich、A. S. Lyakhov

  DOI：10.1007/s10593-014-1614-0

  日期：2015.1