1-benzyl-3-isopropenyl-5-chloropyrazole | 1218938-56-7

• 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: 1-benzyl-3-isopropenyl-5-chloropyrazole
• 英文别名: 1-benzyl-5-chloro-3-(prop-1-en-2-yl)-1H-pyrazole；1-benzyl-5-chloro-3-(prop-1-en-2-yl)-pyrazole；1-benzyl-5-chloro-3-isopropenyl-1Hpyrazole；1-Benzyl-5-chloro-3-i-propenyl-1h-pyrazole；1-benzyl-5-chloro-3-prop-1-en-2-ylpyrazole
• CAS: 1218938-56-7
• 化学式: C₁₃H₁₃ClN₂
• 分子量: 232.713
• InChiKey: MSDCWQPNLDPFNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  1-benzyl-3-isopropenyl-5-chloropyrazole 在 五氯化磷 作用下， 以 苯 为溶剂， 以91%的产率得到(2-(1-benzyl-5-chloro-1H-pyrazol-3-yl)prop-1-enyl)trichlorophosphonium hexachlorophosphate
  参考文献：
  名称：

  C-烯基取代的吡唑与五氯化磷的磷酸化

  摘要：

  五氯化磷与苯乙烯反应得到不饱和有机磷化合物，其中氯化磷取代基与双键的碳原子相连[1]。N乙烯基取代的唑类也在双键处被磷酸化[2-3]。直到现在还没有研究用五氯化磷磷酸化С-烯基唑。唑循环中具有增强的亲核性的“吡啶”氮原子的存在可以将五氯化磷的攻击导向杂环而不是乙烯基唑的双键，从而产生供体-受体复合物。事实上，五氯化磷与 1-烯丙基3,5-二甲基吡唑的反应导致了供体-受体复合物 I 的形成。DOI：10.1134/S1070363209060358

  DOI：

  10.1134/s1070363209060358
• 作为产物：
  描述：

  在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 5.83h， 生成 1-benzyl-3-isopropenyl-5-chloropyrazole
  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

• Regioselective Synthesis of 3-[2-(Alkylsulfanyl)ethyl]pyrazoles by Reaction of Alkanethiols with 3-Alkenylpyrazoles
  作者：V. A. Kobelevskaya、A. V. Popov、G. G. Levkovskaya、E. V. Rudyakova、I. B. Rozentsveig

  DOI：10.1134/s1070428018100111

  日期：2018.10

  3-Alkenyl-5-chloropyrazoles reacted with alkanethiols on heating to 60°C to afford in good yields 3-[2-(alkylsulfanyl)ethyl]-5-chloropyrazoles as a result of anti-Markovnikov addition to the alkenyl group.

  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。
• 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.
• Phosphorylation of C-alkenylsubstituted pyrazoles with phosphorus pentachloride
  作者：L. I. Larina、E. V. Rudyakova、V. A. Savosik、G. G. Levkovskaya、V. G. Rozinov、M. Yu. Dmitrichenko

  DOI：10.1134/s1070363209060358

  日期：2009.6

  The reaction of phosphorus pentachloride with styrenes affords unsaturated organophosphorus compounds in which the phosphorus chloride substituent is attached to the carbon atom of the double bond [1]. NVinylsubstituted azoles are also phosphorylated at the double bond [2–3]. Phosphorylation of С-alkenylazoles with phosphorus pentachloride was not studied until now. The presence in the azole cycles

  五氯化磷与苯乙烯反应得到不饱和有机磷化合物，其中氯化磷取代基与双键的碳原子相连[1]。N乙烯基取代的唑类也在双键处被磷酸化[2-3]。直到现在还没有研究用五氯化磷磷酸化С-烯基唑。唑循环中具有增强的亲核性的“吡啶”氮原子的存在可以将五氯化磷的攻击导向杂环而不是乙烯基唑的双键，从而产生供体-受体复合物。事实上，五氯化磷与 1-烯丙基3,5-二甲基吡唑的反应导致了供体-受体复合物 I 的形成。DOI：10.1134/S1070363209060358