6-amino-4-isopropyl-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile | 132814-00-7

• 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-4-isopropyl-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• 英文别名: 6-amino-3-methyl-4-propan-2-yl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• CAS: 132814-00-7
• 化学式: C₁₁H₁₄N₄O
• mdl: MFCD01551924
• 分子量: 218.258
• InChiKey: PLRSBOAHFFFGNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2-甲基丙亚基)丙二腈 、 3-甲基-2-吡唑啉-5-酮 生成 6-amino-4-isopropyl-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
  参考文献：
  名称：

  ABBEL-LATIF, FATHY FAHIM, Z. NATURFORSCH. B, 45,(1990) N2, C. 1675-1678

  摘要：

  DOI：

文献信息

• Synthesis of Substituted Pyranopyrazoles under Neat Conditions via a Multicomponent Reaction
  作者：Boreddy Reddy、Arasampattu Nagarajan

  DOI：10.1055/s-0029-1217526

  日期：2009.7

  A simple and efficient synthesis of pyranopyrazoles in good yields via a four-component reaction between an aromatic aldehyde, hydrazine hydrate, ethyl acetoacetate and malononitrile under neat conditions is described.

  描述了一种简单高效的吡喃并吡唑合成方法：在无溶剂条件下，通过芳香醛、水合肼、乙酰乙酸乙酯与丙二腈的四组分反应，以良好的产率得到目标产物。
• Synthesis of pyranopyrazoles using isonicotinic acid as a dual and biological organocatalyst
  作者：Mohammad Ali Zolfigol、Mahsa Tavasoli、Ahmad Reza Moosavi-Zare、Parvin Moosavi、Hendrik Gerhardus Kruger、Morteza Shiri、Vahid Khakyzadeh

  DOI：10.1039/c3ra45289a

  日期：——

  In this study, a green, simple and efficient method for the preparation of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles by means of a one-pot four component condensation reaction of aryl aldehydes, ethyl acetoacetate, malononitrile and hydrazine hydrate is reported. The reaction utilizes isonicotinic acid as a dual and biological organocatalyst at 85 °C under solvent-free conditions.

  在这项研究中，报道了一种绿色、简单且高效的方法，通过采用苯基醛、乙酰乙酸乙酯、马隆腈和水合肼的一锅四组分缩合反应制备6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-二氢吡喃[2,3-c]吡唑。这一反应在无溶剂条件下，以85 °C的温度下，采用异烟酸作为双重生物有机催化剂。
• Using magnetized water as a solvent for a green, catalyst-free, and efficient protocol for the synthesis of pyrano[2,3-c]pyrazoles and pyrano[4′,3′:5,6]pyrazolo [2,3-d]pyrimidines
  作者：Mohammad Bakherad、Ali Keivanloo、Mostafa Gholizadeh、Rahele Doosti、Mohaddese Javanmardi

  DOI：10.1007/s11164-016-2680-y

  日期：2017.2

  A facile, eco-friendly, and highly efficient one-pot four-component protocol is demonstrated for the synthesis of the pyrano[2,3-c]pyrazole and pyrano[4′,3′:5,6]pyrazolo [2,3- d ]pyrimidine derivatives using magnetized water as a new green solvent. Simplicity, short reaction time, high yield, easy work-up, and absence of hazardous organic solvents are the main advantages of this method .

  已证明一种简便，环保，高效的一锅四组分方案可用于合成吡喃并[2,3-c]吡唑和吡喃并[4'，3'：5,6]吡唑并[2， 3- d ]嘧啶衍生物，使用磁化水作为新的绿色溶剂。该方法的主要优点是操作简便，反应时间短，收率高，后处理简便且无有害有机溶剂。
• 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。
• Sodium ascorbate as an expedient catalyst for green synthesis of polysubstituted 5-aminopyrazole-4-carbonitriles and 6-amino-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles
  作者：Hamzeh Kiyani、Maryam Bamdad

  DOI：10.1007/s11164-018-3260-0

  日期：2018.4

  Sodium ascorbate (SA) was used as a safe catalyst for the synthesis of 5-aminopyrazole-4-carbonitriles from the one-pot three-component cyclocondensation (3-CC) of aldehydes, phenylhydrazine, and malononitrile at 50 °C. This 3-CC proceeds in a mixture of ethanol–water as a green reaction medium to give the desired densely functionalized pyrazoles in good to high yields. 6-Amino-1,4-dihydropyrano-[2

  抗坏血酸钠（SA）被用作安全的催化剂，用于在50°C下由醛，苯肼和丙二腈的一锅式三组分环缩合（3-CC）合成5-氨基吡唑-4-腈。这种3-CC在乙醇-水的混合物中作为绿色反应介质进行反应，以高到高收率得到所需的致密官能化的吡唑。在SA存在下，还通过生态友好且简单的四组分环缩合（4-CC）合成了6-氨基-1,4-二氢吡喃基-[2,3-c]吡唑-5-腈。该4-CC在回流水中作为绿色介质进行，以优异的产率和相对较短的反应时间获得了二氢吡喃基-[2，3-c]吡唑产物。这些对环境友好的多组分环凝反应具有一些有趣的优势，包括节省时间，