4,4'-((4-chloro-3-nitrophenyl)methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) | 67376-80-1

• 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'-((4-chloro-3-nitrophenyl)methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)
• 英文别名: 4,4'-[(4-chloro-3-nitrophenyl)methylene]bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)；5,5'-dimethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(4-chloro-3-nitro-phenylmethanediyl)-bis-pyrazol-3-one
• CAS: 67376-80-1
• 化学式: C₂₇H₂₂ClN₅O₄
• 分子量: 515.956
• InChiKey: NGLHBKHTYXSBLV-UHFFFAOYSA-N

物化性质

• 熔点：
  228-235 °C (decomp)
• 沸点：
  708.9±60.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  119.24
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  依达拉奉 生成 4,4'-((4-chloro-3-nitrophenyl)methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)
  参考文献：
  名称：

  DHAMANKAR P. S.; DAVE M. A.; KULKARNI R. S., INDIAN J. CHEM., 1978, B 16, NO 4, 324

  摘要：

  DOI：

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。

• 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。
• Mn-[4-Chlorophenyl-Salicylaldimine-Methylpyranopyrazole]Cl₂ as a Novel Nanostructured Schiff Base Complex and Catalyst
  作者：Ahmad Reza Moosavi-Zare、Hamid Goudarziafshar、Sharmin Dastbaz

  DOI：10.1002/jccs.201600890

  日期：2017.7

  analysis, and UV–vis spectroscopy. The reactivity of nano‐[Mn‐4CSMP]Cl2 as a catalyst was tested on the tandem cyclocondensation–Knoevenagel condensation–Michael reaction between phenylhydrazine and ethyl acetoacetate with various aromatic aldehydes to give 4,4′‐(arylmethylene)‐bis‐(3‐methyl‐1‐phenyl‐1H ‐pyrazol‐5‐ol)s derivatives.

  制备了作为纳米席夫碱配合物的Mn [4-氯苯基水杨基亚胺基甲基吡喃并吡唑] Cl 2（[Mn-4CSMP] Cl 2），并通过傅里叶变换红外光谱，X射线衍射，热重分析，导数热重分析法对其进行了全面表征，扫描电子显微镜，能量色散X射线分析和紫外可见光谱。在苯并肼与乙酰乙酸乙酯与各种芳香醛的串联环缩合-Knoevenagel缩合-Michael反应中测试了纳米[Mn-4CSMP] Cl 2作为催化剂的反应性，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。
• Design, characterization and application of new ionic liquid 1-sulfopyridinium chloride as an efficient catalyst for tandem Knoevenagel–Michael reaction of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one with aldehydes
  作者：Ahmad Reza Moosavi-Zare、Mohammad Ali Zolfigol、Mahmoud Zarei、Abdolkarim Zare、Vahid Khakyzadeh、Alireza Hasaninejad

  DOI：10.1016/j.apcata.2013.07.004

  日期：2013.10

  In this work, novel ionic liquid 1-sulfopyridinium chloride [Pyridine-SO3H]Cl} is synthesized, and characterized by IR, H-1 and C-13 NMR, UV as well as mass spectra. The ionic liquid is used as an efficient, homogeneous and reusable catalyst for the synthesis of 4,4'-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s by tandem Knoevenagel-Michael reaction of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one with various aromatic and hetero-aromatic aldehydes under mild reaction conditions. (C) 2013 Elsevier B.V. All rights reserved.
• 1,3,5-Tris(hydrogensulfato) Benzene: A New and Efficient Catalyst for Synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol) Derivatives
  作者：Zahed KARIMI-JABERI、Baharak POOLADIAN、Masoud MORADI、Ehsan GHASEMI

  DOI：10.1016/s1872-2067(11)60477-4

  日期：2012.11

  1,3,5-Tris(hydrogensulfato) benzene (THSB) was easily prepared by the reaction between phloroglucinol and chlorosulfonic acid in dichloromethane at room temperature. This compound was then used as an efficient catalyst for the synthesis of 4,4'-(arylmethylene)bis(1H-pyrazol-5-ols) through the condensation reactions of 1-phenyl-3-methylpyrazol-5-one with several different aromatic aldehydes in ethanol at 75 degrees C. The present methodology offers several advantages over existing methodologies, such as excellent yields, simple procedure, easy work-up and ecofriendly reaction conditions.