3-amino-1-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-1H-benzo[f]chromene-2-carbonitrile | 1608149-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 3-amino-1-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-1H-benzo[f]chromene-2-carbonitrile
• 英文别名: 3-Amino-1-(5-hydroxy-3-methyl1h-pyrazol-4-yl)-1h-benzo[f]chromene-2-carbonitrile；3-amino-1-(3-methyl-5-oxo-1,2-dihydropyrazol-4-yl)-1H-benzo[f]chromene-2-carbonitrile
• CAS: 1608149-31-0
• 化学式: C₁₈H₁₄N₄O₂
• 分子量: 318.335
• InChiKey: BHUOBCJQBNNYCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  107.95
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-甲基-2-吡唑啉-5-酮 、 2-羟基-1-萘甲醛 、 丙二腈 在 水 、 sodium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以91%的产率得到3-amino-1-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-1H-benzo[f]chromene-2-carbonitrile
  参考文献：
  名称：

  Solvent-free and ‘on-water’ multicomponent assembling of salicylaldehydes, malononitrile and 3-methyl-2-pyrazolin-5-one: A fast and efficient route to the 2-amino-4-(1H-pyrazol-4-yl)-4H-chromene scaffold

  摘要：

  摘要 在研磨过程中，在少量水的存在下，醋酸钠催化的多组分反应使水杨醛、氰基丙烷和3-甲基-2-吡唑啉-5-酮迅速（10分钟）高效地形成取代的2-氨基-4-(1H-吡唑-4-基)-4H-克罗梅烯，产率为90-96%。这种针对取代的2-氨基-4-(1H-吡唑-4-基)-4H-克罗梅烯的快速有效的方法，作为治疗人类炎症性TNFα介导的疾病和不同生物医学应用的有前景的小分子配体，从多样性导向的大规模工艺的角度来看是有益的，代表了一种快速、高效和环保的多组分反应合成概念。

  DOI：

  10.1016/j.crci.2013.08.002

文献信息

• Synergetic effects of naturally sourced metal oxides in organic synthesis: a greener approach for the synthesis of pyrano[2,3-c]pyrazoles and pyrazolyl-4H-chromenes
  作者：Sachin K. Shinde、Megha U. Patil、Shashikant A. Damate、Suresh S. Patil

  DOI：10.1007/s11164-017-3197-8

  日期：2018.3

  A clean and more economic protocol for the synthesis of pyrano[2,3-c]pyrazoles and pyrazolyl-4H-chromenes has been carried out using bael fruit ash (BFA) as a non-conventional natural catalyst in aqueous condition at ambient temperature. The catalyst was obtained from renewable resources by simple thermal treatment to dry rind of Aegle marmelos (Bael) fruit and formation of its active phase was confirmed by AAS, DSC-TGA, XRD, FT-IR, and SEM techniques. The BFA catalyst was found to be a green, highly active, easily biodegradable, and recyclable without loss of activity after the fifth run. The methodology provides an alternative platform to the conventional catalyzed process.

  一种清洁且更经济的合成吡喔[2,3-c]吡唑和吡唑基-4H-色烯的协议已通过使用番木瓜果灰（BFA）作为非常规天然催化剂，在常温下的水相条件下进行。该催化剂由可再生资源制得，通过简单的热处理干燥Aegle marmelos（番木瓜）果皮，活性相的形成通过AAS、DSC-TGA、XRD、FT-IR和SEM技术得到了确认。实验结果表明，BFA催化剂是一种绿色、高活性、易降解且可回收的催化剂，在第五次反应后未出现活性丧失。这种方法为传统催化过程提供了替代平台。
• AIE active multianalyte fluorescent probe for the detection of Cu2+, Ni2+ and Hg2+ ions
  作者：Mehboobali Pannipara、Abdullah G. Al-Sehemi、Ahmad Irfan、Mohammed Assiri、Abul Kalam、Yahya S. Al-Ammari

  DOI：10.1016/j.saa.2018.04.052

  日期：2018.8

  A novel pyrazolyl chromene derivative (Probe 1) displaying aggregation induced emission (AIE) properties that capable of sensing of multiple metal ions has been designed and synthesized. The multi analyte probe exhibits selective sensing for Cu2+ and Ni2+ ions via fluorescence turn-off mechanism and ratiometric selectivity for Hg2+ ions in aqueous media. The extent of binding of the probe with sensitive metal ions has been demonstrated. The experimental results were further investigated by computational means by optimizing the ground state geometries of Probe 1 and its various metal complexes for Probe 1-Ni, Probe 1-Hg and Probe 1-Cu using density functional theory (DFT) at B3LYP/6-31 +g(d,p) (LANL2DZ) level. On the basis of binding energies, the stability of metal complexes has been studied. In Probe 1-Ni and Probe 1-Cu complexes, charge transfer has been observed from Probe 1 to metal ions revealing ligand to metal charge transfer (LMCT) while in Probe1-Hg complex LMCT as well as intra-molecular charge tranfer (ICT) within Probe 1. (C) 2018 Elsevier B.V. All rights reserved.