3,4,4-trichloro-3-butenoyl chloride | 484067-66-5

• 分子结构分类: 有机化合物 - 有机卤素化合物
• 英文名称: 3,4,4-trichloro-3-butenoyl chloride
• 英文别名: 3,4,4-trichlorobut-3-enoyl chloride
• CAS: 484067-66-5
• 化学式: C₄H₂Cl₄O
• 分子量: 207.871
• InChiKey: KBLIFINHXBWCBS-UHFFFAOYSA-N

物化性质

• 沸点：
  38-39 °C
• 密度：
  1.558 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• 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：

  3,4,4-trichloro-3-butenoyl chloride 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 30.0h， 以65%的产率得到2-bromo-3,4,4-trichloro-3-butenoyl chloride
  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：

  3,4,4-trichloro-3-butenoic acid 在 氯化亚砜 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 以95%的产率得到3,4,4-trichloro-3-butenoyl chloride
  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

• Functionally Substituted Amides and Esters of 3,4,4-Trichloro-3-butenoic Acid
  作者：S. K. Petkevich、E. A. Dikusar、V. I. Potkin、R. V. Kaberdin、K. L. Moiseichuk、A. P. Yuvchenko、P. V. Kurman

  DOI：10.1023/b:rugc.0000031862.88263.de

  日期：2004.4

  Substituted amides and esters of 3,4,4-trichloro-3-butenoic acid were prepared by reactions of its chloride with appropriate amines and alcohols. Treatment of 3,4,4-trichloro-3-butenomorpholide and tert-butyl 3,4,4-trichloro-3-butenoate results in nucleophilic substitution of the internal chlorine atom with the morpholine residue, accompanied by prototropic allyl rearranoement.
• ——
  作者：E. A. Dikusar、N. G. Kozlov、V. I. Potkin、S. K. Petkevich、S. N. Sokolov、N. V. Kovganko

  DOI：10.1023/a:1024112109166

  日期：——

  Esters 1b-15b were synthesized by reacting terpenols 1a-7a, sterols 8a-12a, and plant phenols 13a-15a with 3,4,4-trichloro-3-butenyl chloride.
• Synthesis of mono-and 1,1′-bis(3,4,4-trichlorobut-3-enoyl)-ferrocenes and 3,4,4-trichlorobut-3-enoylcymantrene
  作者：V. I. Potkin、V. L. Shirokii、S. K. Petkevich、P. V. Kurman

  DOI：10.1134/s1070363208080185

  日期：2008.8

  Friedel-Crafts acylation of ferrocene and cymantrene with 3,4,4-trichlorobut-3-enoyl chloride gave the corresponding trichloroallyl terrocenyl and cymantrenyl ketones. The reaction with ferrocene involved either one or both cyclopentadienyl fragments, depending on the reactant ratio. The acylation of acetylferrocene with 3,4,4-trichlorobut-3-enoyl chloride afforded 1-acetyl-1'-(3.4,4-trichlorobut-3-enoyol)ferrocene.
• 5-(Naphth-1-yl)- and 5-[(1,1′-biphenyl)-4-yl]isoxazole-3-carbaldehyde oximes: Synthesis, complexes with palladium, and application in catalysis
  作者：V. I. Potkin、N. A. Bumagin、V. M. Zelenkovskii、S. K. Petkevich、M. V. Livantsov、N. E. Golantsov

  DOI：10.1134/s1070363214090242

  日期：2014.9

  1-(Naphth-1-yl)- and 1-[(1,1'-biphenyl)-4-yl-3,4,4-trichloro-3-buten-1-ones were synthesized by acylation of naphthalene and biphenyl with 3,4,4-trichloro-3-butenoyl chloride. Further reaction with hydroxylamine led to 5-(naphth-1-yl)- and 5-[(1,1'-biphenyl)-4-yl]isoxazole-3-carbaldehyde oximes. The latter form complexes with palladium, which possess high catalytic activity in the Suzuki reaction in aqueous and aqueous-alcoholic media.
• Synthesis and reactions with N-nucleophiles of 1-(thien-2-yl)- and 1-(4-hydroxyphenyl)-3,4,4-trichloro-3-buten-1-ones
  作者：V. I. Potkin、S. K. Petkevich、P. V. Kurman

  DOI：10.1134/s1070428010090071

  日期：2010.9

  Acylation of thiophene and phenol with 3,4,4-trichloro-3-butenoyl chloride afforded the corresponding 1-(thien-2-yl)- and 1-(4-hydroxyphenyl)-3,4,4-trichloro-3-buten-1-ones, whose reaction with amines led to the formation of 3-amino-1-(thien-2-yl, 4-hydroxyphenyl)-4,4-dichloro-2-buten-1-ones The heterocyclization of the initial ketones into pyrazole structure was not observed, and the reaction with hydrazine hydrate provided bispyrazole products, N,N'-bis(5-thien-2-yl)- and N,N'-bis[5-(4-hydroxyphenyl)-1H-pyrazol-3-ylmethylene]hydrazines.