3,4-二氯-3-丁烯-2-酮 | 91157-97-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,4-二氯-3-丁烯-2-酮
• 英文名称: 1,2-dichlorovinyl methyl ketone
• 英文别名: methyl 1,2-dichlorovinyl ketone；3,4-dichlorobut-3-en-2-one
• CAS: 91157-97-0
• 化学式: C₄H₄Cl₂O
• 分子量: 138.981
• InChiKey: OSHAOHOGGBLDCB-UHFFFAOYSA-N

物化性质

• 沸点：
  61.5-62 °C(Press: 30 Torr)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  7
• 可旋转键数：
  1
• 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：

  3,4-二氯-3-丁烯-2-酮 在 sodium sulfide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以87%的产率得到bis(2-chloro-3-oxo-1-butenyl) sulfide
  参考文献：
  名称：

  Synthesis of Bis(2-acyl-2-chlorovinyl) Sulfides

  摘要：

  DOI：

  10.1007/s11178-005-0381-x
• 作为产物：
  描述：

  methyl 1,2,2-trichloroethyl ketone 在 sodium carbonate 作用下， 以 水 为溶剂， 以47.2 g的产率得到3,4-二氯-3-丁烯-2-酮
  参考文献：
  名称：

  1,2-二氯乙烯基烷基酮的合成，结构与特征

  摘要：

  开发了一种从酰卤和1,2-二氯乙烯制备烷基1,2-二氯乙烯酮的方法。通过红外光谱、氢谱和碳谱，测量偶极矩，并使用RHF和B3LYP方法在6–311++G (d,p)基组下进行量子化学计算，研究了烷基1,2-二氯乙烯酮的构型平衡和电子结构。烷基1,2-二氯乙烯酮在Z，s-cis构型中是稳定的，其中烯烃质子与羰基氧形成分子内氢键。1,2-二氯乙烯酮与烷基肼反应生成1-烷基-3-烷基-4-氯吡唑。烷基1,2-二氯乙烯酮与1,1-二甲基肼的反应涉及脱氯化并生成1,1-二甲基肼氯化铵和一系列结构不确定的化合物混合物。

  DOI：

  10.1007/s11178-005-0064-7

文献信息

• Process for preparation of 4-acetyl-2-substituted-imidazoles
  申请人：Pfizer Inc.

  公开号：US04482723A1

  公开（公告）日：1984-11-13

  Novel intermediates of the formula ##STR1## where R.sup.1 and R.sup.2 are each (C.sub.1 -C.sub.4)alkyl or taken together are (C.sub.2 -C.sub.4)alkylene, and their use in a process for preparation of compounds of the formula ##STR2## where R is (C.sub.1 -C.sub.6)alkyl or (CH.sub.2).sub.n Ar, Ar is phenyl or phenyl monosubstituted by Cl, Br, F, CH.sub.3 or OCH.sub.3 and n is 2 to 4; which comprises contacting one of said intermediates with an amidine of formula ##STR3## in the presence of reaction inert solvent and base; and a process for preparing a further intermediate, 1,2-dichloro-1-buten-3-one.

  该专利描述了一种中间体的新型式，其化学式为##STR1##其中R.sup.1和R.sup.2分别为(C.sub.1 -C.sub.4)烷基或一起为(C.sub.2 -C.sub.4)亚烷基，以及它们在制备化合物的过程中的用途，该化合物的化学式为##STR2##其中R为(C.sub.1 -C.sub.6)烷基或(CH.sub.2).sub.n Ar，Ar为苯或被Cl、Br、F、CH.sub.3或OCH.sub.3单取代的苯，n为2到4；包括在惰性反应溶剂和碱的存在下，将其中一种中间体与公式为##STR3##的酰胺基反应，以及一种制备进一步中间体1,2-二氯-1-丁烯-3-酮的方法。
• Distinguishing Features of reactions of 2-chloro-and 2,2-dichloro(bromo)vinyl ketones with alkyl-and arylhydrazines
  作者：G. V. Bozhenkov、V. A. Savosik、L. I. Larina、L. V. Klyba、E. R. Zhanchipova、A. N. Mirskova、G. G. Levkovskaya

  DOI：10.1134/s1070428008070129

  日期：2008.7

  2-Chlorovinyl alkyl ketones react with alkylhydrazines to give mixtures of 1-R-3-R'- and 1-R-5-R'-pyrazoles: The 1-R-3-R'-pyrazoles form through the heterocyclization of 2-chlorovinyl ketone alkylhydrazones whereas in the heterocyclization into 1-R-5-R'-pyrazoles N1-alkyl-N2-(2-acylvinyl) hydrazines are involved. The regiospecific heterocyclization of 2-chloro- and 2,2-dichlorovinyl ketones with arylhydrazines and also of 2,2-dichloro(bromo) vinyl trifluoromethyl ketones with C alkylhydrazines into pyrazoles and 5-chloro(bromo)pyrazoles proceeds through a stage of haloenones hydrazones formation. The study of the structure of the obtained 1-alkyl-3(5)-alkylpyrazoles by means of two-dimenaional H-1 and C-13 NMR spectroscopy and GC-MS method made it possible to assign the proton and carbon signals of isomeric pyrazoles and to establish the diagnostic ions for the pair of 1,3- and 1,5-isomers.
• 5(4)-Chloro-1-(2,4-dinitrophenyl)pyrazoles from 2,4-Dinitrophenylhydrazones of Chlorovinyl Ketones and β,β-Dichloroacrolein
  作者：G. V. Bozhenkov、G. G. Levkovskaya、A. N. Mirskova、L. I. Larina

  DOI：10.1007/s10593-005-0238-9

  日期：2005.7
• Synthesis and properties of 2-amino-1-chloroenones
  作者：G. V. Bozhenkov、V. A. Savosik、A. N. Mirskova、G. G. Levkovskaya

  DOI：10.1134/s1070428007010022

  日期：2007.1

  Reactions of alkyl-, allyl-, and arylamines and o-aminophenol with 1,2-dichlorovinyl alkyl ketones involve replacement of only one chlorine atom in the beta-position with respect to the carbonyl group with formation of 2-alkylamino-, 2-allylamino-, and 2-arylamino-1-chlorovinyl ketones. Diamines of the aromatic and aliphatic series react with 1,2-dichlorovinyl alkyl ketone molecules to give N,N'-bis(2-acyl-2-chlorovinyl)-substituted diamines.
• Synthesis, structure, and characteristics of 1,2-dichlorovinyl alkyl ketones
  作者：G. V. Bozhenkov、G. G. Leckovskaya、L. I. Larina、P. E. Ushakov、G. V. Dolgushin、A. N. Mirskova

  DOI：10.1007/s11178-005-0064-7

  日期：2004.11

  A method of alkyl 1,2-dichlorovinyl ketones preparation from acyl halides and 1,2-dichloroethylene was developed. The configurational equilibrium and electronic structure of alkyl 1,2-dichlorovinyl ketones was investigated by IR, 1H and 13C NMR spectroscopy, by measuring dipole moments, and by quantum-chemical calculations using methods RHF and B3LYP in the basis 6–311++G (d,p). Alkyl 1,2-dichlorovinyl ketones are stable in the Z, s-cis-configuration where the olefin proton is involved into an intramolecular hydrogen bond with the oxygen of the carbonyl group. Reaction of 1,2-dichlorovinyl ketones with alkylhydrazines afforded 1-alkyl-3-alkyl-4-chloropyrazoles. The reaction of alkyl 1,2-dichlorovinyl ketones with 1,1-dimethylhydrazine involved dehydrochlorination and afforded 1,1-dimethylhydrazinium hydrochloride and a mixture of compounds with uncertain structure.

  开发了一种从酰卤和1,2-二氯乙烯制备烷基1,2-二氯乙烯酮的方法。通过红外光谱、氢谱和碳谱，测量偶极矩，并使用RHF和B3LYP方法在6–311++G (d,p)基组下进行量子化学计算，研究了烷基1,2-二氯乙烯酮的构型平衡和电子结构。烷基1,2-二氯乙烯酮在Z，s-cis构型中是稳定的，其中烯烃质子与羰基氧形成分子内氢键。1,2-二氯乙烯酮与烷基肼反应生成1-烷基-3-烷基-4-氯吡唑。烷基1,2-二氯乙烯酮与1,1-二甲基肼的反应涉及脱氯化并生成1,1-二甲基肼氯化铵和一系列结构不确定的化合物混合物。