2-amino-4-(4-cyanophenyl)-4H-benzo[h]chromene-3-carbonitrile | 1021426-95-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 2-amino-4-(4-cyanophenyl)-4H-benzo[h]chromene-3-carbonitrile
• CAS: 1021426-95-8
• 化学式: C₂₁H₁₃N₃O
• 分子量: 323.354
• InChiKey: XQUOMMBWBQNBPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  82.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4-(4-cyanophenyl)-4H-benzo[h]chromene-3-carbonitrile 在 N-氯代丁二酰亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  An approach towards the oxidation of 2-amino-4H-chromenes to 2-imino-2H-chromenes

  摘要：

  A novel method for the synthesis of 2-imino-2H-benzo[h]chromenes via the sequential addition of N-chlorosuccinimide and triethylamine to 2-amino-4H-benzo[h]chromenes has been established. This reaction protocol represents an efficient synthetic strategy to form iminochromene derivatives under mild reaction conditions, which utilizes readily accessible aminochromenes as starting materials and tolerates a wide range of substrates. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.11.046
• 作为产物：
  描述：

  萘酚 、 4-氰基苯甲醛 、 丙二腈 在 nano silica bonded aminoethylpiperazine 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以90%的产率得到2-amino-4-(4-cyanophenyl)-4H-benzo[h]chromene-3-carbonitrile
  参考文献：
  名称：

  Nano silica-bonded aminoethylpiperazine: a highly efficient and reusable heterogeneous catalyst for the synthesis of 4H-chromene and 12H-chromeno[2,3-d]pyrimidine derivatives

  摘要：

  纳米二氧化硅与 3-氯丙基三甲氧基硅烷反应，然后与氨乙基哌嗪处理，得到了纳米二氧化硅键合氨乙基哌嗪（SB-APP）。通过 FT-IR、TGA、BET、SEM 和元素分析对合成的 SB-APP 的结构进行了表征，并确定其为制备 2-氨基-4H-苯和 12H-苯并[2,3-d]嘧啶衍生物的高效碱性催化剂。在温和的反应条件下，苯酚、芳香醛和丙二腈在催化量 SB-APP 的存在下进行一锅三组分反应，可获得高产率的相应 2-氨基-4H-色烯。12H-色烯并[2,3-d]嘧啶通过 2-氨基-4H-色烯与醋酸酐在同一锅中反应而成功合成，且产率合理，相应的色烯中间体无需纯化。所有产物均通过傅立叶变换红外光谱、1H NMR、13C NMR 和 MS 数据进行了表征。催化剂可从反应混合物中简单回收并多次重复使用，催化活性不会明显降低。

  DOI：

  10.1007/s13738-015-0607-y

文献信息

• Heterogeneous ditopic ZnFe₂O₄catalyzed synthesis of 4H-pyrans: further conversion to 1,4-DHPs and report of functional group interconversion from amide to ester
  作者：Paramita Das、Arghya Dutta、Asim Bhaumik、Chhanda Mukhopadhyay

  DOI：10.1039/c3gc42095g

  日期：——

  Highly stable, environmentally benign ZnFe2O4 nanopowder was prepared, characterized and applied in the one-pot, three-component synthesis of 4H-pyrans in water. The ZnFe2O4 catalyst provides both acidic (Fe3+) and basic functionalities (O2−) as the reaction requires. The advantages of this method lie in its simplicity, cost effectiveness, environmental friendliness and easier scaling up for large scale synthesis. Water was exploited both as a reaction medium as well as a medium for synthesis of the catalyst. Moreover, water was the only byproduct. The present report puts forward an application of 4H-pyrans for the synthesis of 1,4-DHPs. This is the first attempt towards the synthesis of 4H-pyran-3-carboxylate from 4H-pyran-3-carboxamide. The corresponding functional group interconversion from amide to ester is rare in organic synthesis.

  成功制备、表征并应用了一种稳定且对环境友好的ZnFe2O4纳米粉，在水相中实现了4H-吡喃的一锅法三组分合成。ZnFe2O4催化剂同时提供了反应所需的酸性（Fe3+）和碱性（O2−）功能。该方法的优势在于其简单性、成本效益、环境友好性以及更易于放大进行大规模合成。水既被用作反应介质，也被用作催化剂的合成介质。此外，水是唯一的副产品。本报告提出了一种应用4H-吡喃合成1,4-二氢吡啶（1,4-DHPs）的方法。这是首次尝试从4H-吡喃-3-甲酰胺合成4H-吡喃-3-羧酸酯。在有机合成中，从酰胺到酯的功能团转换是罕见的。
• “One-pot” access to dihydrofurans via tandem oxidative difunctionalization and ring contraction of aminopyrans
  作者：Santhosh Reddy Mandha、Manjula Alla、Jagadeesh Babu Nanubolu

  DOI：10.1039/c4ob00324a

  日期：——

  An operationally simple and efficient protocol for the construction of dihydrofuran derivatives has been accomplished via a sequential addition of N-chlorosuccinimide and a base to 2-amino-4H-pyran derivatives in alcohol medium. The one-pot protocol proceeding via tandem oxidative difunctionalization and ring contraction provides an entirely new strategy for the construction of the dihydrofuran skeleton.

  通过在醇介质中依次添加N-氯代琥珀酰亚胺和碱，实现了一种操作简便且高效的构建二氢呋喃衍生物的协议。这一单锅法协议通过串联氧化双功能化和环收缩反应，为二氢呋喃骨架的构建提供了一种全新的策略。
• Serendipitous Observation of Liquid-Phase Size Selectivity inside a Mesoporous Silica Nanoreactor in the Reaction of Chromene with Formic Acid
  作者：Paramita Das、Suman Ray、Piyali Bhanja、Asim Bhaumik、Chhanda Mukhopadhyay

  DOI：10.1002/cctc.201701975

  日期：2018.5.24

  product switches from pyrimidine to enol lactones and δ‐keto acids inside the nanoreactor. The shape/size selectivity in the liquid phase is a highly desired phenomenon in organic synthesis. We prepared four different varieties of porous silica materials to obtain this product selectivity. Very high yields of these biologically relevant compounds surpass that achieved by existing methodologies. Again

  在液相色谱中，作为纳米反应器的MCM-41内，在色烯与甲酸的水解/脱羧反应序列中，观察到了前所未有的产品形状/尺寸选择性。预计烯会在与HCOOH的反应中形成嘧啶。然而，在此偶然地，产物从嘧啶变为烯醇内酯和δ纳米反应器内部的酮酸。液相中的形状/尺寸选择性是有机合成中非常需要的现象。我们准备了四种不同的多孔二氧化硅材料，以获得这种产品的选择性。这些生物学上相关的化合物的非常高的产率超过了现有方法所获得的产率。再次，尽管很少有香豆素融合的烯醇内酯的报道，但是这种方法可以轻松合成萘融合的烯醇内酯。此外，这是在许多水解/脱羧/开环/互变异构/脱羧步骤之后的第一个δ-酮酸的一般合成方法。
• DABCO‐Catalyzed Efficient Synthesis of Naphthopyran Derivatives via One‐Pot Three‐Component Condensation Reaction at Room Temperature
  作者：Saeed Balalaie、Sorour Ramezanpour、Morteza Bararjanian、Jürgen H. Gross

  DOI：10.1080/00397910701862865

  日期：2008.3.1

  (DABCO) has been used as a mild and efficient catalyst for synthesis of 2‐amino‐3‐cyano naphthopyran derivatives via a one‐pot three‐component reaction of aromatic aldehydes, naphthols, and malononitrile at room temperature. The short reaction times, easy workup, good to excellent yields, and mild reaction conditions make this domino Knoevenagel–Michael reaction both practical and attractive.

  摘要 二氮杂双环 [2.2.2] 辛烷 (DABCO) 已被用作一种温和高效的催化剂，通过芳香醛、萘酚和丙二腈的一锅三组分反应合成 2-氨基-3-氰基萘并吡喃衍生物。室内温度。反应时间短、后处理简单、产率好到极好以及反应条件温和，使这种多米诺 Knoevenagel-Michael 反应既实用又有吸引力。
• Ultrasonic accelerated efficient synthesis of aminobenzochromenes using Ag ₂ Cr ₂ O ₇ nanoparticles as a reusable heterogeneous catalyst
  作者：Mitra Ebrahimi、Shahrzad Abdolmohammadi、Reza Kia‐Kojoori

  DOI：10.1002/jhet.3915

  日期：2020.4

  Ag2Cr2O7 nanoparticles were found to be an exceedingly effective catalyst for the mild and green synthesis of aminobenzochromenes. The reaction was performed under ultrasonic irradiation as an innocuous tool and in water as a green solvent at room temperature. This method encompasses several sustainable and economic benefits.

  发现Ag 2 Cr 2 O 7纳米颗粒是用于氨基苯并二氢萘酮的温和绿色合成的极其有效的催化剂。反应在室温下在无害工具的超声辐射下和在作为绿色溶剂的水中进行。这种方法具有多种可持续性和经济效益。