6-amino-1,4-dihydro-4-(4-isopropylphenyl)-3-methyl-1-phenylpyrano[2,3-c]pyrazole-5-carbonitrile | 300731-67-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-amino-1,4-dihydro-4-(4-isopropylphenyl)-3-methyl-1-phenylpyrano[2,3-c]pyrazole-5-carbonitrile
• 英文别名: 6-amino-4-(4-isopropylphenyl)-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile；6-Amino-3-methyl-1-phenyl-4-[4-(propan-2-yl)phenyl]-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile；6-amino-3-methyl-1-phenyl-4-(4-propan-2-ylphenyl)-4H-pyrano[2,3-c]pyrazole-5-carbonitrile
• CAS: 300731-67-3
• 化学式: C₂₃H₂₂N₄O
• 分子量: 370.454
• InChiKey: LXJINESGIGRZIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  76.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  依达拉奉 、 4-异丙基苯甲醛 、 丙二腈 以 甘油 为溶剂， 反应 1.33h， 以93%的产率得到6-amino-1,4-dihydro-4-(4-isopropylphenyl)-3-methyl-1-phenylpyrano[2,3-c]pyrazole-5-carbonitrile
  参考文献：
  名称：

  Glycerol as a biodegradable and reusable promoting medium for the catalyst-free one-pot three component synthesis of 4H-pyrans

  摘要：

  甘油作为绿色、生物可降解且可重复利用的促进介质，在无催化剂条件下用于一锅法三组分合成4H-吡喃。广泛的一系列底物，包括芳香和杂环醛、吲哚醌衍生物、苊醌和九氢吲哚，与具有活性α-亚甲基的羰基化合物及烷基丙二酸酯进行缩合反应。所有反应均在短时间内完成，产物收率良好至优异。反应介质可回收并重复使用多次，效率无任何损失。

  DOI：

  10.1039/c2gc35135h

文献信息

• Silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (SB-DBU)Cl as a highly efficient, heterogeneous and recyclable silica-supported ionic liquid catalyst for the synthesis of benzo[b]pyran, bis(benzo[b]pyran) and spiro-pyran derivatives
  作者：Alireza Hasaninejad、Nooshin Golzar、Maryam Beyrati、Abdolkarim Zare、Mohammad Mahdi Doroodmand

  DOI：10.1016/j.molcata.2013.02.022

  日期：2013.6

  The reaction of 3-chloropropyl silica (SilprCl) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dry acetone affords silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (SB-DBU)Cl as a new silica-supported ionic liquid catalyst. Afterward, (SB-DBU)Cl is used for the efficient synthesis of 4H-benzo[b]pyran derivatives via the one-pot, three-component reaction of carbonyl compounds (cyclohexane-1

  3-氯丙基二氧化硅（SilprCl）与1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）在干燥的丙酮中的反应得到二氧化硅键合的5-正丙基-八氢-嘧啶基[1,2- a]氯化ze嗪（SB-DBU）Cl作为新型的二氧化硅负载型离子液体催化剂。之后，（SB-DBU）Cl通过羰基化合物（环己烷-1,3-二酮，5,5-一锅法）的三锅法有效合成4 H-苯并[ b ]吡喃衍生物。（1，3-二甲基环己烷-1，3-二酮或3-甲基-1-苯基-2-吡唑啉-5-酮）与芳族醛和烷基丙二酸酯。此外，一些新颖的双（苯并[ b使用（SB-DBU）Cl合成[] pyran] s和在结构上含有羟吲哚和/或喹喔啉部分的多种结构多样的螺-吡喃。将催化剂循环使用十五次，收率不变。
• Silica bonded n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride (SB-DABCO): A highly efficient, reusable and new heterogeneous catalyst for the synthesis of 4H-benzo[b]pyran derivatives
  作者：Alireza Hasaninejad、Mohsen Shekouhy、Nooshin Golzar、Abdolkarim Zare、Mohammad Mahdi Doroodmand

  DOI：10.1016/j.apcata.2011.04.012

  日期：2011.7

  3-chloropropyl silica with diazabicyclo[2.2.2]octane in dry acetone affords silica bonded n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride (SB-DABCO) as a new basic catalyst. The catalyst is used for the efficient synthesis of 4H-benzo[b]pyran derivatives via one-pot three-component reaction of cyclic ketones/1,3-diketones with aromatic aldehydes and alkylmalonates.

  3-氯丙基二氧化硅与二氮杂双环[2.2.2]辛烷在干燥丙酮中的反应提供了与二氧化硅键合的正丙基-4-氮杂-1-氮杂双环[2.2.2]辛烷氯化物（SB-DABCO），作为一种新的碱性催化剂。通过环酮/ 1,3-二酮与芳族醛和丙二酸烷基酯的一锅三组分反应，该催化剂可用于高效合成4 H-苯并[ b ]吡喃衍生物。
• Morpholine triflate promoted one-pot, four-component synthesis of dihydropyrano[2,3-c]pyrazoles
  作者：Chen-Feng Zhou、Jian-Jun Li、Wei-Ke Su

  DOI：10.1016/j.cclet.2016.05.010

  日期：2016.11

  Abstract A one-pot, four-component reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes, and malononitrile was discussed using Lewis acid catalyst morpholine triflate (MorT) to afford a series of dihydropyrano[2,3- c ]pyrazoles, which were generally catalyzed by organic alkalis. Moderate to excellent yields, no chromatographic purification, and evasion of environmentally hazardous solvents

  摘要利用路易斯酸催化剂吗啉三氟甲磺酸酯（MorT）讨论了乙酰乙酸乙酯，水合肼，醛和丙二腈的一锅四组分反应，制得了一系列二氢吡喃并[2,3-c]吡唑。由有机碱催化。中等至极佳的收率，无需色谱纯化，并且在反应过程中避免使用对环境有害的溶剂，因此该方案对学术界和工业界非常有用。
• Novel silica sodium carbonate (SSC): Preparation, characterization and its first catalytic application to the synthesis of new dihydropyrano[2,3-c]pyrazoles
  作者：Khalil Eskandari、Bahador Karami、Saeed Khodabakhshi

  DOI：10.1016/j.catcom.2014.05.029

  日期：2014.9

  novel and highly efficient catalyst was produced from a reaction between silica chloride and sodium hydrogen carbonate. This novel catalyst was named silica sodium carbonate (SSC), and was characterized by FT-IR, XRD, XRF and TG-DT analyses, atomic absorption and titration with HCl (0.01 N). Furthermore, herein, the first application of SSC as a green, highly efficient and recyclable catalyst to the synthesis

  在这项研究中，新型的高效催化剂是由氯化硅与碳酸氢钠之间的反应制得的。这种新型催化剂称为二氧化硅碳酸钠（SSC），并通过FT-IR，XRD，XRF和TG-DT分析，原子吸收和HCl（0.01 N）滴定进行表征。此外，在本文中，成功地检验了SSC作为绿色，高效且可循环使用的催化剂在合成新的1,4-二氢吡喃并[2,3-c]吡唑中的首次应用。与经典的合成1,4-二氢吡喃并[2,3-c]吡唑的反应相比，本方法使用SSC的方法比其他方法具有一些优势，例如，产品收率高，反应时间短，绿色环保，操作简便。催化剂的处理和可重复使用性。
• An environmentally friendly synthesis of 1,4-dihydropyrano[2,3-c]pyrazole derivatives catalyzed by tungstate sulfuric acid
  作者：Mahnaz Farahi、Bahador Karami、Iman Sedighimehr、Hamideh Mohamadi Tanuraghaj

  DOI：10.1016/j.cclet.2014.07.012

  日期：2014.12

  An efficient three-component synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles via a reaction between 3-methyl-1-phenyl-2-pyrazolin-5-one, aromatic aldehydes and malononitrile using tungstate sulfuric acid as a catalyst was described. Mild conditions, good to excellent yields, easily available catalyst and easy work-up are the key features of this method. (C) 2014 Bahador Karami. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.