4,4'-(naphthalen-2-ylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) | 1314252-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,4'-(naphthalen-2-ylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)
• 英文别名: 4,4'-[(2-naphthyl)methylene]bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)；4,4'-[(2-naphthyl)methylene]bis(3-methyl-1-phenyl-1Hpyrazol-5-ol)；4,4'-[(2-naphthyl)methylene]bis(3-methyl-1-phenyl-pyrazol-5-ol)；4,4'-[(2-naphthyl)methylene]bis(3-methyl-1-phenylpyrazol-5-ol)
• CAS: 1314252-95-3
• 化学式: C₃₁H₂₆N₄O₂
• 分子量: 486.573
• InChiKey: CALFSDZYYSDTHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  37.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  76.1
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  苯肼 在 1-methyl-3-(trimethoxysilylpropyl)-imidazoliumhydrogen sulfate supported on sodium montmorillonite 作用下， 以 neat (no solvent) 为溶剂， 反应 0.44h， 生成 4,4'-(naphthalen-2-ylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)
  参考文献：
  名称：

  纳米多孔Na +-蒙脱土负载的布朗斯台德酸性离子液体催化一锅合成4,4′-（芳基亚甲基）-双-（3-甲基-1-苯基-1 H-吡唑-5-醇）

  摘要：

  通过将1-甲基-3-（三甲氧基甲硅烷基丙基）-咪唑硫酸氢盐离子液体固定在纳米孔Na +-蒙脱石上而获得的Na + -MMT- [pmim] HSO 4被用作催化剂以简单有效地合成4通过苯基肼，乙酰乙酸乙酯和醛的一锅缩合反应得到4,4- （芳基亚甲基）-双-（3-甲基-1-苯基-1 H-吡唑-5-醇）衍生物。这些反应在无溶剂条件下于80°C进行，反应时间短，收率高。催化剂的低负载，简单的实验程序和使用廉价的催化剂是该程序的一些优点。同样，该催化剂可以重复使用几次而不会损失其催化活性。

  DOI：

  10.1016/j.molliq.2015.04.027

文献信息

• Synthesis and characterization of two novel biological-based nano organo solid acids with urea moiety and their catalytic applications in the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol), coumarin-3-carboxylic acid and cinnamic acid derivatives under mild and green conditions
  作者：Mohammad Ali Zolfigol、Roya Ayazi-Nasrabadi、Saeed Baghery

  DOI：10.1039/c5ra14001c

  日期：——

  Green and straight-forward syntheses of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol) derivatives using nano structure organocatalysts, namely 2-carbamoylhydrazine-1-sulfonic acid and carbamoylsulfamic acid, have been developed.

  利用纳米结构有机催化剂，即2-氨基甲酰肼-1-磺酸和氨基甲酰磺酸，直接绿色合成4,4′-(芳基亚甲基)双(1H-吡唑-5-醇)衍生物的方法已经被开发出来。

• Sulfonated rice husk ash (RHA-SO3H) as a highly efficient and reusable catalyst for the synthesis of some bis-heterocyclic compounds
  作者：Mohadeseh Seddighi、Farhad Shirini、Manouchehr Mamaghani

  DOI：10.1039/c3ra44053b

  日期：——

  Sulfonated rice husk ash (RHA-SO3H), a newly reported solid acid catalyst, was efficiently used for the synthesis of 4,4′-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ols), 3,3′-(arylmethylene)-bis-(4-hydroxycoumarins) and bis(indolyl)methanes. The procedure gave the products in excellent yields within very short reaction times under mild and green conditions. Also this catalyst can be reused several times without appreciable loss of its catalytic activity.

  磺化稻壳灰（RHA-SO3H），一种新近报道的固体酸催化剂，被高效地用于合成4,4′-（芳基亚甲基）-双-（3-甲基-1-苯基-1H-吡唑-5-醇）、3,3′-（芳基亚甲基）-双-（4-羟基香豆素）以及双（吲哚基）甲烷。该方法在温和且环保的条件下，利用极短的反应时间即可获得优异的产率。此外，该催化剂可多次重复使用，且其催化活性无明显损失。
• Tandem cyclocondensation-Knoevenagel–Michael reaction of phenyl hydrazine, acetoacetate derivatives and arylaldehydes
  作者：Ardeshir Khazaei、Fatemeh Abbasi、Ahmad Reza Moosavi-Zare

  DOI：10.1039/c4nj01079e

  日期：——

  In this work, a novel N-bromo sulfonamide reagent, namely N,2-dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide (DCDBTSD), is synthesized and fully characterized by IR, UV, 1H and 13C NMR, XRD, TG/DTG as well as mass spectra. The presented N-bromo sulfonamide is used as a new and highly efficient catalyst for the synthesis of 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s via one-pot pseudo five component condensation reaction of phenylhydrazine, acetoacetate derivatives and arylaldehydes. Mechanistically, Br+ ions, which are generated by the catalyst, can catalyze this reaction in neutral media. This methodology offers several advantages, such as use of non-toxic and inexpensive materials, high yields, short reaction times and clean workup.

  本研究合成了一种新型 N-溴磺酰胺试剂，即 N,2-二溴-6-氯-3,4-二氢-2H-苯并[e][1,2,4]噻二嗪-7-磺酰胺 1,1-二氧化物（DCDBTSD），并通过红外光谱、紫外光谱、1H 和 13C NMR、XRD、TG/DTG 以及质谱对其进行了全面表征。所提出的 N-溴磺酰胺被用作一种新型高效催化剂，通过苯肼、乙酰乙酸衍生物和芳基醛的单锅伪五组分缩合反应合成 4,4â²-（芳基亚甲基）-双（3-甲基-1-苯基-1H-吡唑-5-醇）。从机理上讲，催化剂产生的 Br+ 离子可在中性介质中催化这一反应。这种方法具有多种优势，如使用无毒、廉价的材料，产率高、反应时间短和操作简便。
• 2-Hydroxyethylammonium acetate as a reusable and cost-effective ionic liquid for the efficient synthesis of bis(pyrazolyl)methanes and 2-pyrazolyl-1-nitroalkanes
  作者：Sara Sobhani、Razieh Nasseri、Moones Honarmand

  DOI：10.1139/v2012-059

  日期：2012.10

  A new and convenient method for the synthesis of bis(pyrazolyl)methanes by one-pot tandem Knoevenagel–Michael reaction of 3-methyl-1-phenyl-5-pyrazolone with aryl, heteroaryl, or alkyl aldehydes in the presence of 2-hydroxyethylammonium acetate (2-HEAA) as a task-specific ionic liquid is described. This method was also successfully applied for the synthesis of 2-pyrazolyl-1-nitroalkanes by Michael

  在 2-羟乙基铵存在下，通过 3-甲基-1-苯基-5-吡唑啉酮与芳基、杂芳基或烷基醛的单锅串联 Knoevenagel-Michael 反应合成双（吡唑基）甲烷的新方法描述了醋酸盐 (2-HEAA) 作为特定任务的离子液体。该方法还成功地应用于通过 3-甲基-1-苯基-5-吡唑啉酮与 β-硝基苯乙烯在短反应时间内的迈克尔加成合成 2-吡唑基-1-硝基烷烃。本协议提供了几个优点，例如使用可重复使用且具有成本效益的离子液体、环境友好的反应介质、易于扩大规模和良好的产品产量。
• Cyclocondensation-Knoevenagel–Michael Domino reaction of phenyl hydrazine, acetoacetate derivatives and aryl aldehydes over acetic acid functionalized ionic liquid
  作者：Ahmad Reza Moosavi-Zare、Mohammad Ali Zolfigol、Ehsan Noroozizadeh、Omid Khaledian、Behzad Shirmardi Shaghasemi

  DOI：10.1007/s11164-015-2317-6

  日期：2016.5

  Abstract An efficient solvent-free protocol for the synthesis of 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1 H -pyrazol-5-ol)s via one-pot pseudo five-component condensation reaction of phenyl hydrazine, ethylacetoacetate, and aryl aldehydes in the presence of acetic acid functionalized pyridinium salt (1-(carboxymethyl)pyridinium chloride [cmpy]Cl}) as reusable catalyst has been reported. Moreover

  摘要 一种通过一锅式假五组分缩合反应合成4,4'-（芳基亚甲基）-双（3-甲基-1-苯基-1 H- 吡唑-5-醇）s的有效无溶剂方案 据报道，在乙酸官能化吡啶鎓盐（1-（羧甲基）吡啶鎓氯化物[cmpy] Cl}）存在下，苯肼，乙酰乙酸乙酯和芳基醛可重复使用。此外，这项工作还研究了1 H和13 C NMR，质量，CHN分析，傅立叶变换红外光谱，扫描电子显微镜，X射线衍射分析以及催化剂的晶格间距计算。 图形概要