1,1,4-trichlorobut-3-en-2-one | 83959-33-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1,4-trichlorobut-3-en-2-one
• 英文别名: 1,1,4-trichloro-3-buten-2-one；1,1,4-Trichloro-3-buten-2-one
• CAS: 83959-33-5
• 化学式: C₄H₃Cl₃O
• 分子量: 173.426
• InChiKey: PVTFYUFIJCGAKB-UHFFFAOYSA-N

物化性质

• 沸点：
  57-60 °C(Press: 7 Torr)
• 密度：
  1.447±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  8
• 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：

  1,1,4-trichlorobut-3-en-2-one 在 sodium sulfide nonahydrate 作用下， 反应 6.0h， 以90%的产率得到4,4'-thiobis(1,1-dichlorobut-3-en-2-one)
  参考文献：
  名称：

  Unusual reaction of chloroacetyl chloride with 1,2-dichloroethene. Synthesis and properties of 2-chlorovinyl dichloromethyl ketone

  摘要：

  The reaction of chloroacetyl chloride with 1,2-dichloroethene in the presence of AlCl3 unexpectedly led to the formation of (E)-1,1,4-trichlorobut-3-en-2-one whose structure was proved by H-1 and C-13 NMR, IR, and mass spectra and independent synthesis. A probable reaction scheme was proposed, which involves transformation of initially formed 1,2,4-trichloro-3-oxobutan-2-yl cation by the action of AlCl3. The high reactivity of the vinylic halogen atom in (E)-1,1,4-trichlorobut-3-en-2-one was demonstrated by its reactions with nitrogen-centered nucleophiles (triethylamine, aniline, 3,5-dimethyl-1H-pyrazole) and sodium sulfide. These reactions involved only the C-Cl bond in the vinyl fragment and afforded (4,4-dichloro-3-oxobut-2-en-1-yl)triethylammonium chloride, 1,1-dichloro-4-phenylaminobut-3-en-2-one, 1-(4,4-dichloro-3-oxobut-2-en-1-yl)-3,5-dimethyl-1H-pyrazole, and 4,4'-thiobis(1,1-dichlorobut-3-en-2-one), respectively. The reaction of 1,1,4-trichlorobut-3-en-2-one with benzylhydrazine gave a mixture of 1,3- and 1,5-disubstituted pyrazoles.

  DOI：

  10.1134/s1070428008120038
• 作为产物：
  描述：

  反-1,2-二氯乙烯 、 氯乙酰氯 在 三氯化铝 作用下， 反应 11.0h， 以70%的产率得到1,1,4-trichlorobut-3-en-2-one
  参考文献：
  名称：

  Unusual reaction of chloroacetyl chloride with 1,2-dichloro-ethylene. Synthesis of 1,1,4-trichlorobut-3-en-2-one

  摘要：

  DOI：

  10.1134/s1070428008010211

文献信息

• Method for the Production of N-Substituted (3-Dihalomethyl-1-Methyl-Pyrazole-4-yl) Carboxamides
  申请人：Zierke Thomas

  公开号：US20100174094A1

  公开（公告）日：2010-07-08

  The present invention relates to a process for preparing N-substituted (3-dihalomethylpyrazol-4-yl)carboxamides of the formula (I) in which R 1 is optionally substituted phenyl or C 3 -C 7 -cycloalkyl, R 1a is hydrogen or fluorine, or R 1a together with R 1 is optionally substituted C 3 -C 5 -alkanediyl or C 5 -C 7 -cycloalkanediyl, R 2 is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, X is F or Cl and n is 0, 1, 2 or 3; which comprises A) providing a compound of the formula (II) in which X is F or Cl, Y is Cl or Br and R 2 has one of the meanings given above and B) reacting a compound of the formula (II) with carbon monoxide and a compound of the formula (III) in which R 1 , R 1a and n have one of the meanings given above; in the presence of a palladium catalyst; to intermediates used for the preparation according to the process according to the invention, and also to processes for their preparation.

  本发明涉及一种制备式(I)的N-取代(3-二卤甲基吡唑-4-基)羧酰胺的方法 其中R1是可选的取代苯基或C3-C7环烷基，R1a是氢或氟，或者R1a与R1一起是可选的取代C3-C5-烷二基或C5-C7-环烷二基，R2是C1-C6-烷基，C2-C6-烯基，C2-C6-炔基或C1-C4-烷氧基-C1-C2-烷基，X是F或Cl，n为0、1、2或3；包括 A)提供式(II)的化合物 其中X是F或Cl，Y是Cl或Br，R2具有上述给定的含义之一 B)将式(II)的化合物与一氧化碳和式(III)的化合物反应 其中R1、R1a和n具有上述给定的含义之一；在钯催化剂的存在下； 用于根据本发明的方法制备的中间体，以及用于它们的制备的方法。
• Method for the production of N-substituted (3-dihalomethyl-1-methylpyrazol-4-yl) carboxamides
  申请人：BASF SE

  公开号：US08153820B2

  公开（公告）日：2012-04-10

  The present invention relates to a process for preparing N-substituted (3-dihalomethylpyrazol-4-yl)carboxamides of the formula (I) in which R1 is optionally substituted phenyl or C3-C7-cycloalkyl, R1a is hydrogen or fluorine, or R1a together with R1 is optionally substituted C3-C5-alkanediyl or C5-C7-cycloalkanediyl, R2 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C1-C4-alkoxy-C1-C2-alkyl, X is F or Cl and n is 0, 1, 2 or 3; which comprises A) providing a compound of the formula (II) in which X is F or Cl, Y is Cl or Br and R2 has one of the meanings given above and B) reacting a compound of the formula (II) with carbon monoxide and a compound of the formula (III) in which R1, R1a and n have one of the meanings given above; in the presence of a palladium catalyst; to intermediates used for the preparation according to the process according to the invention, and also to processes for their preparation.

  本发明涉及一种制备式（I）的N-取代（3-二卤甲基吡唑-4-基）羧酰胺的方法，其中R1是可选取代的苯基或C3-C7环烷基，R1a是氢或氟，或者R1a与R1一起是可选取代的C3-C5烷二基或C5-C7环烷二基，R2是C1-C6烷基，C2-C6烯基，C2-C6炔基或C1-C4-烷氧基-C1-C2-烷基，X是F或Cl，n为0，1，2或3。该方法包括：A）提供式（II）的化合物，其中X为F或Cl，Y为Cl或Br，R2具有上述给定的含义；和B）在钯催化剂的存在下，将式（II）的化合物与一种式（III）的化合物反应，其中R1，R1a和n具有上述给定的含义，以制备用于根据本发明方法的制备的中间体，以及用于它们的制备的方法。
• Unusual reaction of chloroacetyl chloride with 1,2-dichloroethene. Synthesis and properties of 2-chlorovinyl dichloromethyl ketone
  作者：G. V. Bozhenkov、V. A. Savosik、E. V. Rudyakova、Kha Kuok Khan’、A. I. Albanov、L. V. Klyba、A. N. Mirskova、G. G. Levkovskaya

  DOI：10.1134/s1070428008120038

  日期：2008.12

  The reaction of chloroacetyl chloride with 1,2-dichloroethene in the presence of AlCl3 unexpectedly led to the formation of (E)-1,1,4-trichlorobut-3-en-2-one whose structure was proved by H-1 and C-13 NMR, IR, and mass spectra and independent synthesis. A probable reaction scheme was proposed, which involves transformation of initially formed 1,2,4-trichloro-3-oxobutan-2-yl cation by the action of AlCl3. The high reactivity of the vinylic halogen atom in (E)-1,1,4-trichlorobut-3-en-2-one was demonstrated by its reactions with nitrogen-centered nucleophiles (triethylamine, aniline, 3,5-dimethyl-1H-pyrazole) and sodium sulfide. These reactions involved only the C-Cl bond in the vinyl fragment and afforded (4,4-dichloro-3-oxobut-2-en-1-yl)triethylammonium chloride, 1,1-dichloro-4-phenylaminobut-3-en-2-one, 1-(4,4-dichloro-3-oxobut-2-en-1-yl)-3,5-dimethyl-1H-pyrazole, and 4,4'-thiobis(1,1-dichlorobut-3-en-2-one), respectively. The reaction of 1,1,4-trichlorobut-3-en-2-one with benzylhydrazine gave a mixture of 1,3- and 1,5-disubstituted pyrazoles.
• Unusual reaction of chloroacetyl chloride with 1,2-dichloro-ethylene. Synthesis of 1,1,4-trichlorobut-3-en-2-one
  作者：G. V. Bozhenkov、V. A. Savosik、E. V. Rudyakova、A. N. Mirskova、G. G. Levkovskaya

  DOI：10.1134/s1070428008010211

  日期：2008.1