5-chloro-3-ethenyl-1-methyl-1H-pyrazole | 1278588-26-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5-chloro-3-ethenyl-1-methyl-1H-pyrazole
• 英文别名: 1-Methyl-3-vinyl-5-chloropyrazole；5-chloro-3-ethenyl-1-methylpyrazole
• CAS: 1278588-26-3
• 化学式: C₆H₇ClN₂
• 分子量: 142.588
• InChiKey: HTBGZOOYNZKFJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  丙烷-1-硫醇 、 5-chloro-3-ethenyl-1-methyl-1H-pyrazole 以 苯 为溶剂， 反应 1.0h， 以83%的产率得到5-chloro-1-methyl-3-[2-(propylsulfanyl)ethyl]-1H-pyrazole
  参考文献：
  名称：

  烷硫醇与3-烯基吡唑的反应区域选择性合成3- [2-（烷基硫烷基）乙基]吡唑

  摘要：

  3-烯基-5-氯吡唑在加热至60℃时与链烷硫醇反应，由于反马氏链烯基加到马尔可夫尼科夫基团上，因此以良好的收率得到3- [2-（烷基硫烷基）乙基] -5-氯吡唑。

  DOI：

  10.1134/s1070428018100111
• 作为产物：
  描述：

  5-chloro-3-(1-chloroethyl)-1-methyl-1H-pyrazole 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以72%的产率得到5-chloro-3-ethenyl-1-methyl-1H-pyrazole
  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

• Directed synthesis of 3-(2,2-dichlorocyclopropyl)pyrazoles
  作者：V. A. Kobelevskaya、A. V. Popov、A. Ya. Nikitin、G. G. Levkovskaya

  DOI：10.1134/s1070428017010298

  日期：2017.1

  1-Alkyl-3-(2,2-dichlorocyclopropyl)-1H-pyrazoles have been synthesized by cyclopropanation of the corresponding 3-vinylpyrazoles with dichlorocarbene generated from chloroform or sodium trichloroacetate and tested for insecticidal activity.

  通过将相应的3-乙烯基吡唑与由氯仿或三氯乙酸钠生成的二氯卡宾环丙烷化，可以合成1-烷基-3-（2,2-二氯环丙基）-1 H-吡唑，并测试其杀虫活性。
• Synthesis of 3-(5-chloropyrazol-3-yl)propenals
  作者：Alexandr V. Popov、Valentina A. Kobelevskaya、Lyudmila I. Larina、Galina G. Levkovskaya

  DOI：10.1016/j.mencom.2017.03.024

  日期：2017.3

  The Vielsmeier–Haack formylation of 5-chloro-3-alkenylpyrazoles proceeds at the olefinic double bond and affords (2E)-3-(5-chloro-1H-pyrazol-3-yl)prop-2-enals.

  5-氯-3-烯基吡唑的Vielsmeier-Haack甲酰化反应在烯烃双键处进行，得到（2E）-3-（5-氯-1H-吡唑-3-基）丙-2-烯。
• Selective synthesis of 3-[1-(organylsulfanyl)ethyl]- and 3-[2-(organylsulfanyl)ethyl]-5-chloro-1H-pyrazoles
  作者：D. O. Samultsev、E. V. Rudyakova、G. G. Levkovskaya

  DOI：10.1134/s1070428012100259

  日期：2012.10
• Synthesis of previously unknown 3,3′-linearly linked sulfur- and selenium-containing bispyrazoles by reactions of 3-alkenyl-5-chloropyrazoles with bischalcogenols
  作者：E. V. Rudyakova、D. O. Samultsev、E. P. Levanova、G. G. Levkovskaya

  DOI：10.1134/s1070428013050175

  日期：2013.5

  By reactions of 3-alkenyl-5-chloropyrazoles with appropriate dichalcogenols the fi rst specimens were obtained of previously unknown 3,3'-linearly linked bispyrazoles containing in the alkyl chain of the linker two heteroatoms, sulfur or selenium. 3-Vinyl-5-chloropyrazoles react with 1,3-propanedithiol, 2-hydroxy-1,3-propanedithiol, and 2-hydroxy-1,3-propanediselenol under UV irradiation and heating at 60A degrees C over 8 h affording products of the addition against Markovnikoff rule. The radical addition of 1,3-propanedithiol to 3-isopropenyl-5-chloropyrazole required a longer time, 15 h.
• 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.