1-(2,5-dimethylphenyl)-3,4,4-trichloro-3-buten-1-one | 521081-05-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,5-dimethylphenyl)-3,4,4-trichloro-3-buten-1-one
• 英文别名: 3,4,4-trichloro-1-(2,5-dimethylphenyl)but-3-en-1-one
• CAS: 521081-05-0
• 化学式: C₁₂H₁₁Cl₃O
• 分子量: 277.578
• InChiKey: XMTMDKNDMLWQSY-UHFFFAOYSA-N

物化性质

• 熔点：
  48-49 °C(Solv: ethanol (64-17-5))
• 沸点：
  394.2±42.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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-(2,5-dimethylphenyl)-3,4,4-trichloro-3-buten-1-one 在 盐酸 、 sodium tetrahydroborate 、 硫酸 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 反应 19.0h， 生成 3,4,4-trichloro-1-(2,5-dimethylphenyl)but-3-en-1-amine hydrochloride
  参考文献：
  名称：

  Synthesis of functional derivatives of aryl trichlorovinyl (trichloroallyl) ketones via consecutive transformations of the carbonyl group

  摘要：

  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.

  DOI：

  10.1134/s1070428014100042
• 作为产物：
  描述：

  对二甲苯 、 3,4,4-trichloro-3-butenoyl chloride 在 三氯化铝 作用下， 以70%的产率得到1-(2,5-dimethylphenyl)-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

• Structure and Magnetic Properties of A Novel Complex of Copper(II) Chloride With 3-(Hydroxyiminomethyl)-5-(2,5-Dimethylphenyl)Isoxazole
  作者：O. G. Shakirova、N. V. Kuratieva、L. G. Lavrenova、A. S. Bogomyakov、S. K. Petkevich、V. I. Potkin

  DOI：10.1007/s10947-010-0103-2

  日期：2010.8

  A method is developed to prepare a complex of copper(II) chloride with 3-(hydroxyiminomethyl)-5-(2,5-dimethylphenyl)isoxazole (L) of the composition [Cu2L2(μ-Cl)2Cl2]. Its molecular and crystal structure is determined by single crystal X-ray diffraction. Examination of the curve μef(T) within the 2-300 K temperature range reveals the presence of antiferromagnetic interactions between unpaired electrons

  开发了一种制备氯化铜 (II) 与组成为 [Cu2L2(μ-Cl)2Cl2] 的 3-(羟基亚氨基甲基)-5-(2,5-二甲基苯基)异恶唑 (L) 络合物的方法。其分子和晶体结构由单晶X射线衍射确定。检查 2-300 K 温度范围内的曲线 μef(T) 揭示了铜 (II) 的未配对电子之间存在反铁磁相互作用。
• 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、R. V. Kaberdin、S. K. Petkevich、P. V. Kurman

  DOI：10.1023/a:1020980921916

  日期：——

  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.
• 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.