2,2-dichlorovinyl 1-chloroethyl ketone | 1194617-74-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dichlorovinyl 1-chloroethyl ketone
• 英文别名: 1,1,4-trichloropent-1-en-3-one
• CAS: 1194617-74-7
• 化学式: C₅H₅Cl₃O
• 分子量: 187.453
• InChiKey: CVEWVJQXEHVRQK-UHFFFAOYSA-N

物化性质

• 沸点：
  104-106 °C(Press: 20 Torr)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2,2-dichlorovinyl 1-chloroethyl ketone 在 三乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 5-氯-3-乙烯基-1-乙基吡唑
  参考文献：
  名称：

  3-Alkenyl-5-chloropyrazoles: expedient synthesis via heterocyclization of 1,1-dichloro-4-halo-1-alken-3-ones with hydrazines

  摘要：

  Synthesis of hard-to-reach 5-chloro-3-alkenylpyrazoles was developed via heterocyclization of alkyl-, benzyl- or dialkylhydrazines with 1,1-dichloro-4-halo-1-alken-3-ones obtained from haloacyl chlorides and vinylidene chloride. The reaction process includes the formation of intermediate 5-chloro-3-(1-haloalkyl)pyrazoles followed by dehydrohalogenation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.028
• 作为产物：
  描述：

  在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以12.02 g的产率得到2,2-dichlorovinyl 1-chloroethyl ketone
  参考文献：
  名称：

  3-Alkenyl-5-chloropyrazoles: expedient synthesis via heterocyclization of 1,1-dichloro-4-halo-1-alken-3-ones with hydrazines

  摘要：

  Synthesis of hard-to-reach 5-chloro-3-alkenylpyrazoles was developed via heterocyclization of alkyl-, benzyl- or dialkylhydrazines with 1,1-dichloro-4-halo-1-alken-3-ones obtained from haloacyl chlorides and vinylidene chloride. The reaction process includes the formation of intermediate 5-chloro-3-(1-haloalkyl)pyrazoles followed by dehydrohalogenation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.028

文献信息

• Synthesis of poly-functionalized pyrazoles under Vilsmeier-Haack reaction conditions
  作者：Aleksandr V. Popov、Valentina A. Kobelevskaya、Ludmila I. Larina、Igor B. Rozentsveig

  DOI：10.24820/ark.5550190.p010.934

  日期：——

  Synthesis of 1,3-disubstituted 5-chloro-1H-pyrazole-4-carbaldehydes was achieved by formylation of the corresponding 5-chloro-1H-pyrazoles under Vilsmeier-Haack conditions.

  1,3-二取代的 5-氯-1H-吡唑-4-甲醛的合成是通过在 Vilsmeier-Haack 条件下相应的 5-氯-1H-吡唑的甲酰化来实现的。
• Synthesis and reactions of 1-benzyl-3-haloalkyl-5-chloropyrazoles
  作者：E. V. Rudyakova、V. A. Savosik、I. T. Evstaf’eva、E. V. Kondrashov、G. G. Levkovskaya

  DOI：10.1134/s1070428009050108

  日期：2009.5

  pyrazoles reacted with indole and pyrrole in DMSO in the presence of alkali to give 3-(heter-1-yl)alkyl-substituted 1-benzyl-5-chloropyrazoles. 1-[(1-Benzyl-5-chloropyrazol-3-yl)methyl]indole reacted regiospecifically with chloroal trifluoromethylsulfonyl- and 4-chlorophenylsulfonylimines providing the products of C-amidotrichloroethylation into the position 3 of the indole ring. 1-[(1-Benzyl-5-c

  在碱存在下，合成的1-苄基-3-氯烷基-5-氯吡唑与吲哚和吡咯在DMSO中反应，得到3-（杂-1-基）烷基取代的1-苄基-5-氯吡唑。1-[（（1-苄基-5-氯吡唑-3-基）甲基]吲哚与氯醛三氟甲基磺酰基-和4-氯苯基磺酰亚胺类在区域上发生反应，从而将C-酰胺基三氯乙基化的产物带入吲哚环的3位。通过1-[（1-苄基-5-氯吡唑-3-基）甲基的反应获得1-[（1-苄基-5-氯吡唑-3-基）甲基]吲哚-3-基}磺酰乙酸。 ]-吲哚与碘，硫脲和氯乙酸。
• A Regioselective Synthesis of 5-chloro-1-vinyl- and 3-alkenyl-5-chloro-1H-pyrazoles
  作者：Valentina А. Kobelevskaya、Ludmila I. Larina、Alexandr V. Popov

  DOI：10.1007/s10593-022-03139-x

  日期：2022.11

  5-Chloro-1-vinyl-1Н-pyrazoles were obtained by elimination of hydrogen chloride from the corresponding 5-chloro-1-(2-chloroethyl)-1Н-pyrazoles by the action of NaOH in EtOH or t-BuOK in pyridine. The synthesis of 5-chloro-3-propyl-1-vinyl-1H-pyrazole-4-carbaldehyde was carried out by the treatment of 5-chloro-1-(2-chloroethyl)-3-propyl-1H-pyrazole-4-carbaldehyde with t-BuOK in pyridine. 3-Alkenyl-5-chl

  2,2-二氯乙烯基酮与2-(羟乙基)肼反应，生成3-取代的5-氯-1-(2-羟乙基)-1H-吡唑。在氯化亚砜存在下，在CHCl3中回流加热1-(2-羟乙基)-1H-吡唑，生成5-氯-1-(2-氯乙基)-1H-吡唑。在乙醇中用NaOH或在吡啶中用t-BuOK，从相应的5-氯-1-(2-氯乙基)-1H-吡唑中消除氯化氢，得到5-氯-1-乙烯基-1H-吡唑。在吡啶中用t-BuOK处理5-氯-1-(2-氯乙基)-3-丙基-1H-吡唑-4-甲醛，合成5-氯-3-丙基-1-乙烯基-1H-吡唑-4-甲醛。在DMF中，在150°C下从相应的3-(α-氯烷基)-1H-吡唑中消除HCl，生成3-烯基-5-氯-1-(2-氯乙基)-1H-吡唑。
• 3-Alkenyl-5-chloropyrazoles: expedient synthesis via heterocyclization of 1,1-dichloro-4-halo-1-alken-3-ones with hydrazines
  作者：Galina G. Levkovskaya、Valentina A. Kobelevskaya、Elena V. Rudyakova、Khanh Q. Ha、Dmitrii O. Samultsev、Igor B. Rozentsveig

  DOI：10.1016/j.tet.2011.01.028

  日期：2011.3

  Synthesis of hard-to-reach 5-chloro-3-alkenylpyrazoles was developed via heterocyclization of alkyl-, benzyl- or dialkylhydrazines with 1,1-dichloro-4-halo-1-alken-3-ones obtained from haloacyl chlorides and vinylidene chloride. The reaction process includes the formation of intermediate 5-chloro-3-(1-haloalkyl)pyrazoles followed by dehydrohalogenation. (C) 2011 Elsevier Ltd. All rights reserved.