5-hexyl-3-phenyl-1H-pyrazole | 1037423-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-hexyl-3-phenyl-1H-pyrazole
• CAS: 1037423-05-4
• 化学式: C₁₅H₂₀N₂
• 分子量: 228.337
• InChiKey: MUFFUGKVJGLITR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-1-phenyl-1-nonen-3-one 在 四(三苯基膦)钯 alkaline H₂O₂ 、 一水合肼 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 20.02h， 生成 5-hexyl-3-phenyl-1H-pyrazole
  参考文献：
  名称：

  钯（0）催化α，β-环氧酮异构化为β-二酮†

  摘要：

  在催化量的四（三苯基膦）钯（0）​​和1,2-双（二苯基膦基）乙烷的存在下，α，β-环氧酮以高收率异构化为相应的β-二酮。开链和环状底物均可使用。讨论了可能的反应机理。

  DOI：

  10.1002/recl.19881070324

文献信息

• A highly efficient heterogeneous palladium-catalyzed cascade three-component reaction of acid chlorides, terminal alkynes and hydrazines leading to pyrazoles
  作者：Qiurong Chen、Fang Yao、Lin Yin、Mingzhong Cai

  DOI：10.1016/j.jorganchem.2015.12.037

  日期：2016.2

  MCM-41-immobilized palladium(II) complex [MCM-41-2N–Pd(OAc)2] and 1.0 mol% of CuI, acid chlorides were coupled with terminal alkynes in Et3N at 50 °C to give α,β-unsaturated ynones, which were converted in situ into pyrazoles by the cycloaddition of hydrazines at room temperature with acetonitrile as cosolvent. The cascade reactions generated a variety of pyrazole derivatives in moderate to good yields, and

  在0.5摩尔％的3-（2-氨基乙基氨基）丙基官能化的MCM-41固定的钯（II）配合物[MCM-41-2N-Pd（OAc）2 ]和1.0摩尔％的CuI的存在下，酰氯将其与末端炔烃在50°C的Et 3 N中偶合，得到α，β-不饱和炔酮，通过在室温下以乙腈为助溶剂将肼环加成，将其原位转化为吡唑。级联反应以中等至良好的产率生成了多种吡唑衍生物，并且这种非均相钯催化剂显示出比PdCl 2（PPh 3）2更高的催化活性，并且可以被回收并重复使用至少10次连续试验而活性没有降低。
• Synthesis of 3,5-Disubstituted-1H-Pyrazoles from Acid Chlorides, Alkynes, and Hydrazine in the Presence of Silica-Supported-Zinc Bromide
  作者：Ali Keivanloo、Mohammad Bakherad、Shahrzad Samangooei

  DOI：10.3184/174751915x14382642961716

  日期：2015.8

  An efficient one-pot palladium- and copper-free procedure has been developed for a convenient synthesis of 3,5 -disubstituted-1H-pyrazoles from various acid chlorides, terminal alkynes and hydrazine by a coupling reaction and cyclocondensation sequence. Acid chlorides react with terminal alkynes in the presence of silica-supported-zinc bromide to give α,β-unsaturated ynones, and in situ conversion

  已开发出一种高效的一锅式无钯和无铜工艺，可通过偶联反应和环缩合顺序从各种酰氯、末端炔烃和肼方便地合成 3,5-二取代-1H-吡唑。在二氧化硅负载的溴化锌存在下，酰氯与末端炔烃反应生成 α,β-不饱和炔酮，并通过肼环缩合反应原位转化为吡唑。
• Copper on iron promoted one-pot synthesis of β-aminoenones and 3,5-disubstituted pyrazoles
  作者：Szabolcs Kovács、Zoltán Novák

  DOI：10.1016/j.tet.2013.08.047

  日期：2013.10

  The reaction of hydroximoyl chlorides with acetylenes in the presence of a copper on iron bimetallic system leads to beta-aminoenones via reductive ring opening of isoxazole intermediates. The valuable beta-aminoenone building blocks can be isolated or transformed into pyrazoles with the addition of hydrazine in a straightforward one-pot procedure. (C) 2013 Elsevier Ltd. All rights reserved.
• Highly Regioselective Synthesis of 1-Acyl-5-hydroxypyrazolines or Synthesis of 3,5-Disubstituted Pyrazoles from (E)-β-Chlorovinyl Ketones and Benzohydrazides or Hydrazine Hydrate
  作者：Taolei Sun、Jingli Zhang、Haotian Wu、Rongrong Hou、Ye Yuan、Bifeng Chen

  DOI：10.3987/com-20-14251

  日期：——

  Highly regioselective synthesis of 1-acyl-5-hydroxypyrazolines or synthesis of 3,5-disubstituted pyrazoles have been achieved through the cyclocondensation of (E)/beta-chlorovinyl ketones with benzohydrazides/hydrazine hydrate under extremely mild reaction conditions. The mechanistic studies showed that diverse electrophilic pathways of (E)-beta-chlorovinyl ketones could be observed by using different nucelophilic species. Moreover, the utility of the tandem reaction is further illustrated by the concise synthesis of 1-acyl-pyrazole and 3-pentyl-5-phenyl-1H-pyrazole.
• One-pot three-component synthesis of pyrazoles through a tandem coupling-cyclocondensation sequence
  作者：Hai-Ling Liu、Huan-Feng Jiang、Min Zhang、Wen-Juan Yao、Qiu-Hua Zhu、Zhou Tang

  DOI：10.1016/j.tetlet.2008.03.153

  日期：2008.6

  An efficient and general one-pot procedure for the synthesis of pyrazoles from acid chlorides, terminal alkynes and hydrazines was described via a coupling and cyclocondensation sequence. Acid chlorides coupled with terminal alkynes to give alpha,beta-unsaturated ynones, and in situ converted into pyrazoles by the cycloaddition of hydrazines. The desired pyrazoles were obtained with 15-85% isolated yields. (C) 2008 Published by Elsevier Ltd.