(3,5-dimethyl-1H-pyrazol-1-yl)(thiophen-2-yl)methanone | 351419-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (3,5-dimethyl-1H-pyrazol-1-yl)(thiophen-2-yl)methanone
• 英文别名: 3,5-dimethyl-1-(thiophene-2-carbonyl)-1H-pyrazole；(3,5-dimethylpyrazol-1-yl)-thiophen-2-ylmethanone
• CAS: 351419-53-9
• 化学式: C₁₀H₁₀N₂OS
• mdl: MFCD00593302
• 分子量: 206.268
• InChiKey: JAJPDRXLBIESQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3,5-dimethyl-1H-pyrazol-1-yl)(thiophen-2-yl)methanone 、 双(乙腈)氯化钯(II) 以 二氯甲烷 为溶剂， 以62%的产率得到dichlorobis(2-(3,5-dimethylpyrazolyl-1-carbonyl)thiophene)palladium(II)
  参考文献：
  名称：

  呋喃酰基和噻吩羰基接头吡唑基钯 (II) 配合物 ?? 作为乙烯低聚催化剂的合成、表征和评价

  摘要：

  2-呋喃酰氯和 2-噻吩碳酰氯与取代的吡唑反应生成改性吡唑基化合物：{(3,5-Me2pzCO)-2-C4H3O} (L1), {(3,5-Me2pzCO)-2-C4H3S } (L2), {(3,5-t-Bu2pzCO)-2-C4H3O} (L3), {(3,5-t-Bu2pzCO)-2-C4H3S} (L4), {(3,5-Ph2pzCO) )-2-C4H3S} (L5) 和 {(pzCO)-2-C4H3O} (L6) 收率良好。这些合成子与 [Pd(NCMe)2Cl2] 的反应得到相应的单核钯 (II) 配合物：[Pd(L1)2Cl2] (1), [Pd(L2)2Cl2] (2), [Pd(L3)2Cl2 ] (3)、[Pd(L4)2Cl2] (4)、[Pd(L5)2Cl2] (5) 和 [Pd(L6)2Cl2] (6) 的产量中等至高。合成的所有化合物均通过 1H NMR、13C NMR

  DOI：

  10.1139/v05-092
• 作为产物：
  描述：

  2-噻吩甲酰肼 、 乙酰丙酮 在 PEG-SO₃H 作用下， 以 水 为溶剂， 反应 0.08h， 以88%的产率得到(3,5-dimethyl-1H-pyrazol-1-yl)(thiophen-2-yl)methanone
  参考文献：
  名称：

  PEG–SO3H as a mild, efficient and green catalytic system for the synthesis of pyrazole derivatives in aqueous medium

  摘要：

  在水相中使用PEG-SO3H作为酸性催化剂，成功地实现了一种合成一系列吡唑类化合物的多功能、替代性及环境友好型策略。通过涉及二羰基化合物与酰肼/酰肼化合物的单锅反应程序，产物以高收率获得。该新方法完全避免了在此反应中使用有机酸和有毒或昂贵的溶剂。催化剂无废弃物产生，易于制备，并可高效重复使用。

  DOI：

  10.1007/s13738-012-0143-y

文献信息

• Cellulose sulfuric acid as a bio-supported and efficient solid acid catalyst for synthesis of pyrazoles in aqueous medium
  作者：Mohammad Ali Nasseri、Mehri Salimi、Abbas Ali Esmaeili

  DOI：10.1039/c4ra11440j

  日期：——

  A convenient and practical method was described for the regioselective synthesis of pyrazoles from hydrazines/hydrazides and 1,3-dicarbonyl compounds via the Knorr synthesis in water with cellulose sulfuric acid (CSA) as a biopolymer-based solid acid catalyst. Various hydrazines and hydrazides were reacted with 1,3 diketones and the desired pyrazoles were obtained in high yields. The reaction of less

  描述了一种方便实用的方法，用于在水中以纤维素硫酸盐（CSA）作为生物聚合物基固体酸催化剂，通过克诺尔合成法从肼/酰肼和1,3-二羰基化合物进行区域选择性合成吡唑。使各种肼和酰肼与1,3二酮反应，并以高收率获得所需的吡唑。反应性较低的肼与1，3-二羰基化合物的反应在相应的derivatives衍生物处停止。酰肼与β-酮酸酯一起使用，亚胺加合物是唯一的分离产物。简单的产品分离，温和的反应条件，固体酸催化剂的可重复使用性和较短的反应时间是这种绿色程序的优势。
• Mixing with microwaves: solvent-free and catalyst-free synthesis of pyrazoles and diazepines
  作者：Buchi Reddy Vaddula、Rajender S. Varma、John Leazer

  DOI：10.1016/j.tetlet.2013.01.029

  日期：2013.3

  A simple and facile condensation of hydrazines/hydrazides and diamines with 1,3-diketones/beta-ketoester leads to the preparation of pyrazoles and diazepines in high yields. This eco-friendly protocol is accelerated by microwave heating and efficiently carried out without any reaction solvent or catalyst in as little as 5 min. Published by Elsevier Ltd.
• Greener and rapid access to bio-active heterocycles: room temperature synthesis of pyrazoles and diazepines in aqueous medium
  作者：Vivek Polshettiwar、Rajender S. Varma

  DOI：10.1016/j.tetlet.2007.11.017

  日期：2008.1

  An expeditious room temperature synthesis of pyrazoles and diazepines by condensation of hydrazines/hydrazides and diamines with various 1,3-diketones is described. This greener protocol was catalyzed by polystyrene supported sulfonic acid (PSSA) and proceeded efficiently in water in the absence of any organic solvent within 1-2 min. (C) 2007 Elsevier Ltd. All rights reserved.
• PEG–SO3H as a mild, efficient and green catalytic system for the synthesis of pyrazole derivatives in aqueous medium
  作者：M. A. Nasseri、S. A. Alavi、B. Zakeri Nasab

  DOI：10.1007/s13738-012-0143-y

  日期：2013.4

  A versatile, alternative and environmentally benign strategy for the synthesis of a series of pyrazoles has been successfully performed in water using PEG–SO3H as an acidic catalyst. The products are obtained in high yield from the one-pot reaction procedure involving dicarbonyl compounds and hydrazines/hydrazides. This new method totally avoids the use of organic acids and toxic or expensive solvents in this reaction. The catalyst is waste-free, easily prepared, and efficiently re-used.

  在水相中使用PEG-SO3H作为酸性催化剂，成功地实现了一种合成一系列吡唑类化合物的多功能、替代性及环境友好型策略。通过涉及二羰基化合物与酰肼/酰肼化合物的单锅反应程序，产物以高收率获得。该新方法完全避免了在此反应中使用有机酸和有毒或昂贵的溶剂。催化剂无废弃物产生，易于制备，并可高效重复使用。
• Furoyl and thiophene carbonyl linker pyrazolyl palladium(II) complexes — Synthesis, characterization, and evaluation as ethylene oligomerization catalysts
  作者：Stephen O Ojwach、Mmboneni G Tshivhase、Ilia A Guzei、James Darkwa、Selwyn F Mapolie

  DOI：10.1139/v05-092

  日期：2005.6.1

  2-thiophene carbonyl chloride with substituted pyrazoles produced the modified pyrazolyl compounds: (3,5-Me2pzCO)-2-C4H3O} (L1), (3,5-Me2pzCO)-2-C4H3S} (L2), (3,5-t-Bu2pzCO)-2-C4H3O} (L3), (3,5-t-Bu2pzCO)-2-C4H3S} (L4), (3,5-Ph2pzCO)-2-C4H3S} (L5), and (pzCO)-2-C4H3O} (L6) in good yields. Reactions of these synthons with [Pd(NCMe)2Cl2] afforded the corresponding mononuclear palladium(II) complexes: [Pd(L1)2Cl2]

  2-呋喃酰氯和 2-噻吩碳酰氯与取代的吡唑反应生成改性吡唑基化合物：(3,5-Me2pzCO)-2-C4H3O} (L1), (3,5-Me2pzCO)-2-C4H3S } (L2), (3,5-t-Bu2pzCO)-2-C4H3O} (L3), (3,5-t-Bu2pzCO)-2-C4H3S} (L4), (3,5-Ph2pzCO) )-2-C4H3S} (L5) 和 (pzCO)-2-C4H3O} (L6) 收率良好。这些合成子与 [Pd(NCMe)2Cl2] 的反应得到相应的单核钯 (II) 配合物：[Pd(L1)2Cl2] (1), [Pd(L2)2Cl2] (2), [Pd(L3)2Cl2 ] (3)、[Pd(L4)2Cl2] (4)、[Pd(L5)2Cl2] (5) 和 [Pd(L6)2Cl2] (6) 的产量中等至高。合成的所有化合物均通过 1H NMR、13C NMR