4,4'-((1H-indol-3-yl)methanediyl)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) | 1336986-31-2

• 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'-((1H-indol-3-yl)methanediyl)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)
• 英文别名: 4,4'-((1H-indol-3-yl)methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)；4,4`-((1H-indol-3-yl)methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)；bis(5-hydroxy-3-methyl-1-phenyl-pyrazolyl)-(3-indolyl)methane
• CAS: 1336986-31-2
• 化学式: C₂₉H₂₅N₅O₂
• 分子量: 475.55
• InChiKey: KLAZJIWOPVIMPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  36.0
• 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：
  91.89
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  α-(3-indolyl) N-phenyl nitrone 、 依达拉奉 在 dodecatungstosilic acid 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 以86%的产率得到4,4'-((1H-indol-3-yl)methanediyl)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)
  参考文献：
  名称：

  An Unexpected Catalytic Synthesis of Novel and Known Bis(Pyrazolyl) Methanes by the use of α-aryl-N-phenyl Nitrones in Aqueous Media

  摘要：

  在一定量的硅钨酸催化下，在 EtOH/H2O 溶液中，芳基 N-苯基硝基腈与 3-甲基-1-苯基-2-吡唑啉-5-酮反应，意外地得到了高产率的双(3-羟基-1-苯基吡唑基)芳基甲烷，而不是两种可能的 1,3-加成产物。这是首次报道通过硝基化合物和吡唑啉-5-酮反应合成双（3-羟基-1-苯基吡唑基）芳基甲烷。文中提出了这一过程的可能机理。

  DOI：

  10.3184/174751914x14114871789226

文献信息

• A Rapid Tandem Knoevenagel/Michael Reaction Using Mohr’s Salt as a Highly Efficient Catalyst: Green Synthesis of Bis(pyrazolyl)methanes
  作者：Khalil Eskandari、Bahador Karami、Saeed Khodabakhshi、Mahnaz Farahi

  DOI：10.2174/1570178612666141204224826

  日期：2015.1.1

  A convenient access to some new and known bis(pyrazolyl)methanes synthesis has been successfully achieved via an alternative Knoevenagel/Michael reaction of aromatic aldehydes and pyrazole-5-one in the presence of Mohr’s salt as a green catalyst. This novel procedure has some advantages such as high efficiency, simplicity, high rate and environmental safety.

  在莫尔盐作为绿色催化剂的存在下，通过芳香醛和吡唑-5-酮的另一种 Knoevenagel/Michael 反应，成功地合成了一些新的和已知的双（吡唑）甲烷。这种新型方法具有高效、简单、速率高和环境安全等优点。
• Green and efficient synthesis of novel bispyrazoles through a tandem Knoevenagel and Michael type reaction using nanowire zinc oxide as a powerful and recyclable catalyst
  作者：Khalil ESKANDARI、Bahador KARAMI、Saeed KHODABAKHSHI、Seyyed Jafar HOSEINI

  DOI：10.3906/kim-1404-54

  日期：——

  Zinc oxide nanowires (ZnO NWs) were prepared and characterized by scanning electron microscopy, powder X-ray diffraction, and transmission electron microscopy analyses. ZnO NWs were then employed as heterogeneous and recyclable catalyst for green synthesis of some new and known bispyrazole derivatives through a tandem Knoevenagel and Michael type addition reaction of aromatic aldehyde and pyrazolone. The synthetic method is operationally simple and affords product with high yields in short reaction times.

  制备了氧化锌纳米线（ZnO NWs），并通过扫描电子显微镜、粉末 X 射线衍射和透射电子显微镜分析对其进行了表征。然后利用氧化锌纳米线作为异相可回收催化剂，通过芳香醛与吡唑酮的串联克诺文纳格尔和迈克尔加成反应，绿色合成了一些新的和已知的双吡唑衍生物。该合成方法操作简单，反应时间短，产率高。
• PEG-SO3H as a new, highly efficient and homogeneous polymeric catalyst for the synthesis of bis(indolyl)methanes and 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1Hpyrazol-5-ol)s in water
  作者：A. Hasaninejad、M. Shekouhy、A. Zare、S. M. S. Hoseini Ghattali、N. Golzar

  DOI：10.1007/bf03249075

  日期：2011.6

  In this work, a green, simple and highly efficient procedure for the synthesis of bis(indolyl)methanes and 4,4'-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s [as an important class of bis(pyrazolyl) methanes] is described. The condensation of indoles or 1-phenyl-3-methylpyrazol-5-one with carbonyl compounds catalyzed by poly(ethylene glycol)-bound sulfonic acid (PEG-SO3H) in water affords the title compounds in high yields and relatively short reaction times.
• ZnO Nanoparticles – a Recyclable Catalyst for the Synthesis of Bis(Pyrazolyl)Methanes
  作者：K. Eskandari、B. Karami、S. Khodabakhshi

  DOI：10.1007/s10593-015-1635-3

  日期：2015.3

  A one-pot condensation between a wide range of aryl aldehydes and 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one by employing ZnO nanoparticles as recyclable and highly efficient catalyst to produce new and known bis(pyrazolyl)methanes in aqueous media is introduced. This efficient and new method to bis(pyrazolyl)methanes has some advantages, such as the use of a safe and reusable catalyst, simple operation, short reaction times, and good to excellent yields of the products.