2-amino-4-(4-hydroxy-3-methoxyphenyl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-amino-4-(4-hydroxy-3-methoxyphenyl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
• 英文别名: 2-amino-4-(4-hydroxy-3-methoxyphenyl)-6-(hydroxymethyl)-8-oxo-4H-pyrano[3,2-b]pyran-3-carbonitrile
• 化学式: C₁₇H₁₄N₂O₆
• 分子量: 342.308
• InChiKey: XDBFIQGXEPACKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  曲酸 、 2-(4-hydroxy-3-methoxybenzylidene)malononitrile 以 水 为溶剂， 以85%的产率得到2-amino-4-(4-hydroxy-3-methoxyphenyl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
  参考文献：
  名称：

  微波辅助水介导的迈克尔加成反应，合成曲酸衍生物

  摘要：

  描述了在微波辐射下在水的存在下合成取代的曲酸衍生物的高效方法。该转化代表了从简单的起始原料合成曲酸衍生物的有效方法。

  DOI：

  10.1007/s11164-015-2419-1

文献信息

• Ferrocene-Containing Ionic Liquid Supported on Silica Nanospheres (SiO₂@Imid-Cl@Fc) as a Mild and Efficient Heterogeneous Catalyst for the Synthesis of Pyrano[3,2-b]Pyran Derivatives Under Ultrasound Irradiation
  作者：Reza Teimuri-Mofrad、Somayeh Esmati、Masoumeh Rabiei、Mahdi Gholamhosseini-Nazari

  DOI：10.3184/174751918x15161933697754

  日期：2018.1

  A novel heterogeneous silica nanosphere-supported ferrocene-containing ionic liquid catalyst (SiO₂@Imid-Cl@Fc) was designed and synthesised and was systematically characterised by Fourier transform infrared (FTIR) spectroscopy, field emission scanning electron microscopy (FE-SEM), energy dispersive X-ray (EDX) and X-ray diffraction (XRD) analysis. The catalytic activity of the SiO₂@Imid-Cl@Fc catalyst was tested in a one-pot, three-component reaction of malononitrile and kojic acid with 15 aromatic aldehydes at room temperature under ultrasound irradiation. The products were pyrano[3,2-b]pyran derivatives, four of which are new. The catalyst exhibited good catalytic performance over short reaction times (15–20 min) and could be recycled at least five times without significant loss of activity.

  设计并合成了一种新型异相二氧化硅纳米球支撑的含二茂铁离子液体催化剂（SiO2@Imid-Cl@Fc），并通过傅立叶变换红外光谱（FTIR）、场发射扫描电子显微镜（FE-SEM）、能量色散 X 射线（EDX）和 X 射线衍射（XRD）分析对其进行了系统表征。在室温、超声辐照条件下，测试了 SiO2@Imid-Cl@Fc 催化剂在丙二腈和曲酸与 15 种芳香醛的一锅三组分反应中的催化活性。反应产物为吡喃并[3,2-b]吡喃衍生物，其中四种为新产物。该催化剂在较短的反应时间（15-20 分钟）内表现出良好的催化性能，可循环使用至少五次而不会明显丧失活性。
• Supramolecular catalysis by β-cyclodextrin for the synthesis of kojic acid derivatives in water
  作者：Evgeny A. Kataev、Mittapalli Ramana Reddy、Gangarpu Niranjan Reddy、Vemulapati Hanuman Reddy、Cirandur Suresh Reddy、Basi V. Subba Reddy

  DOI：10.1039/c5nj01902h

  日期：——

  An efficient and green method has been developed for the synthesis of kojic acid derivatives by employing 20 mol% β-cyclodextrin in aqueous media.

  已开发出一种高效且环保的方法，通过在水介质中使用20 mol% β-环糊精合成曲酸衍生物。
• Acetic Acid-Mediated Synthesis of Kojic Acid Derivatives
  作者：Y. B. Kiran、G. Rambabu、V. Vijayakumar、L. C. A. Barbosa

  DOI：10.1134/s1070428021070162

  日期：2021.7

  acetic acid-mediated synthesis of kojic acid derivatives through a multicomponent reaction (MCR) has been developed. This new protocol is simple and efficient; it involves a one-pot reaction of equimolar amounts of kojic acid, aromatic aldehydes, and several active methylene compounds at 90°C in 3 h and results in the formation of a wide range of kojic acid derivatives with high yields. Furthermore, the

  摘要 通过多组分反应 (MCR) 开发了一种绿色乙酸介导的曲酸衍生物合成。这个新协议简单而高效；它涉及等摩尔量的曲酸、芳香醛和几种活性亚甲基化合物在 90°C 下在 3 小时内进行一锅反应，并以高产率形成范围广泛的曲酸衍生物。此外，已经探索了在类似反应条件下仅曲酸与苯甲醛反应时无环产物的形成。
• Sonochemistry in an organocatalytic domino reaction: an expedient multicomponent access to structurally functionalized dihydropyrano[3,2-<i>b</i>]pyrans, spiro-pyrano[3,2-<i>b</i>]pyrans, and spiro-indenoquinoxaline-pyranopyrans under ambient conditions
  作者：Biplob Borah、Jahnu Bora、Pambala Ramesh、L. Raju Chowhan

  DOI：10.1039/d2ra01917e

  日期：——

  irradiation in aqueous ethanolic solution at ambient temperature has been developed. This methodology can involve the assembly of C-C, C[double bond, length as m-dash]C, C-O, C-N bonds via a one-pot operation, and following this protocol, a series of novel amino-substituted spiro[indeno[1,2-b]quinoxaline-11,4-pyrano[3,2-b]pyran]-3-carbonitrile/carboxylates have been synthesized. The practical utility of

  一种高度方便且可持续的一锅法，用于多种药用特殊氨基取代的 4,8-二氢吡喃并[3,2-b]吡喃-3-甲腈和螺[indoline-3,4]的多样化合成'-吡喃并[3,2-b]吡喃]-3-甲腈/羧酸酯衍生物，基于容易获得的羰基化合物的多米诺三组分反应，包括芳基醛或靛红、活性亚甲基化合物和作为迈克尔的曲酸已开发出在环境温度下在乙醇水溶液中在超声波照射下使用仲胺催化剂l-脯氨酸的供体。该方法可以涉及通过一锅操作组装CC、C[双键，长度为m-dash]C、CO、CN键，并按照该方案，一系列新型氨基取代的螺[茚并[1]已合成了 ,2-b]喹喔啉-11,4-吡喃并[3,2-b]吡喃]-3-甲腈/羧酸酯。发现该方法的实际用途对于放大反应和其他有用的转化非常有效。该方法具有显着的优点，包括反应条件温和、能源效率高、反应时间短、反应速度快、后处理程序简单、官能团耐受性广泛、使用可重复使用的催化剂、绿色溶剂体系
• Microwave-assisted, water-mediated Michael addition for synthesis of kojic acid derivatives
  作者：Pravin R. Likhar、G. Narshimha Reddy、M. Ramana Reddy

  DOI：10.1007/s11164-015-2419-1

  日期：2016.6

  A highly efficient method is described for the synthesis of substituted kojic acid derivatives in the presence of water under microwave irradiation. This transformation represents an efficient way to synthesize kojic acid derivatives from simple starting materials.

  描述了在微波辐射下在水的存在下合成取代的曲酸衍生物的高效方法。该转化代表了从简单的起始原料合成曲酸衍生物的有效方法。