2-amino-6-chloro-4-(nitromethyl)-4H-chromene-3-carbonitrile | 1253044-56-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-amino-6-chloro-4-(nitromethyl)-4H-chromene-3-carbonitrile
• 英文别名: 2-Amino-6-chloro-4-(nitromethyl)-4h-chromene-3-carbonitrile
• CAS: 1253044-56-2
• 化学式: C₁₁H₈ClN₃O₃
• 分子量: 265.656
• InChiKey: QZRSSDRGPCVRQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-氯代水杨醛 在 四氢吡咯 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 2-amino-6-chloro-4-(nitromethyl)-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  L-(+)-Tryptophan methyl ester derived polymeric microbeads as an efficient heterogeneous catalyst for green synthesis of 2-amino-4-(nitromethyl)-4H-chromene-3- carbonitriles

  摘要：

  通过 N-甲基丙烯酰-L-(+)-色氨酸甲酯（MATrp）与乙二醇二甲基丙烯酸酯（EGDMA）的共聚反应得到了平均直径为 106-300 μm 的交联微珠[poly(EGDMA-MATrp)]，并成功地将其用作异相催化剂，用于硝基甲烷与取代的 2-亚氨基苯并吡喃在水介质中的共轭加成反应。该催化剂以良好的产率合成了多种 2-氨基-4-（硝基甲基）-4H-苯并吡喃-3-甲腈。聚合物微珠非常耐用，可重复使用 5 次，且活性不会明显降低。DFT 计算和实验结果表明，π-π 相互作用以及氢键在反应机理中发挥了重要作用。

  DOI：

  10.55730/1300-0527.3467

文献信息

• Aqueous-mediated Michael Addition of Active Methylene Compounds with Nitroalkenes
  作者：Wenkai Dong、Dongcheng Xu、Jianwu Xie

  DOI：10.1002/cjoc.201200228

  日期：2012.8

  A simple, atom economical and highly efficient green protocol has been developed for the synthesis of Michael adducts of nitroalkenes and 2‐amino‐2‐chromene derivatives by Michael addition of active methylene compounds (such as malononitrile and ethyl cyanoacetate) to nitroalkenes under aqueous‐mediated conditions. This green approach provided the desired products in high yields and the reaction scope

  已开发出一种简单，原子经济且高效的绿色方案，用于在水溶液中，通过将活性亚甲基化合物（如丙二腈和氰基乙酸乙酯）迈克尔加成到硝基烯烃中，合成硝基烯烃和2-氨基-2-色烯衍生物的迈克尔加成产物。介导的条件。这种绿色方法以高收率提供了所需的产物，并且反应范围被证明是相当广泛的。
• Aegle marmelos in heterocyclization: greener, highly efficient, one-pot three-component protocol for the synthesis of highly functionalized 4H-benzochromenes and 4H-chromenes
  作者：Sachin Shinde、Shashikant Damate、Smita Morbale、Megha Patil、Suresh S. Patil

  DOI：10.1039/c6ra28779d

  日期：——

  A facile, one-pot three-component protocol for the synthesis of 2-amino-4H-chromene derivatives has been demonstrated using Bael Fruit Extract (BFE) as a natural catalyst in a green reaction medium. This method offers a mild, efficient and highly economical protocol since the reaction proceeds in natural BFE-catalyst at room temperature under aerobic conditions with a very short reaction time (30 min)

  使用Bael水果提取物（BFE）作为绿色反应介质中的天然催化剂，已经证明了用于合成2-氨基-4 H-色烯衍生物的一种简便的一锅三组分方案。该方法提供了温和，有效和高度经济的方案，因为该反应在需氧条件下于室温下在天然BFE催化剂中进行，在配体/外部催化剂/无外部助催化剂的条件下，反应时间非常短（30分钟），因此，它是现有协议的绿色环保选择。通过热处理，然后水提取Aegle marmelos（bael）果皮的外皮得到催化剂。还发现它是清洁的，高产率的并且具有大规模合成的能力。
• Biocatalytic one-pot three-component synthesis of 4H-chromene derivatives in non-aqueous medium
  作者：Prabhakar Shrivas、Umesh Pratap

  DOI：10.1007/s11696-018-00679-5

  日期：2019.5

  The baker’s yeast catalyzed one-pot three-component cyclocondensation of salicylaldehyde, malononitrile or ethyl cyanoacetate, and nitroalkanes for the synthesis of substituted 2-amino-4H-chromene derivatives is presented. The highlights of the protocol is a use of a biodegradable catalyst which is inexpensive, having simple reaction conditions, in other words, at room temperature and neutral pH, good-to-excellent

  提出了面包酵母催化水杨醛，丙二腈或氰基乙酸乙酯与硝基烷烃的一锅三组分环缩合反应，以合成取代的2-氨基-4 H-亚甲基苯衍生物。该方案的重点是使用廉价的生物可降解催化剂，其具有简单的反应条件，换言之，在室温和中性pH下，良好至优异的产率，以及简单的后处理程序。 图形概要
• Synthesis of <scp>4</scp> <i>H</i> ‐chromene‐isoxazole hybrids via <i>ortho</i> ‐hydroxy directing cyclization of isoxazole‐styrenes and Michael addition of imino‐chromenes in aqueous medium
  作者：Sakkani Nagaraju、Kota Sathish、Dhurke Kashinath

  DOI：10.1002/jhet.4251

  日期：2021.6

  AbstractA green, efficient, and one‐pot method synthesis of functionalized 4H‐chromene‐isoxazole hybrids is reported via o‐hydroxy group directing cyclization of isoxazole‐styrenes and Michael addition of 3,5‐dimethyl‐4‐nitroisoxazole on 2‐imino‐2H‐chromene‐3‐carbonitrile (independent methods). The developed methodology was further extended for nitromethane, malononitrile, and alkylcyanoacetates as Michael donors.
• L-(+)-Tryptophan methyl ester derived polymeric microbeads as an efficient heterogeneous catalyst for green synthesis of 2-amino-4-(nitromethyl)-4H-chromene-3- carbonitriles
  作者：AYŞE HALIÇ POSLU、BİLGEN OSMAN、YUNUS KAYA、ÖMER KOZ、GAMZE KOZ

  DOI：10.55730/1300-0527.3467

  日期：——

  The cross-linked microbeads with average diameter of 106-300 μm, [poly(EGDMA-MATrp)], were obtained by copolymerization reaction of N-methacryloyl-L-(+)-tryptophan methyl ester (MATrp) with ethylene glycol dimethacrylate (EGDMA) and successfully applied as a heterogeneous catalyst in conjugate addition reaction of nitromethane to substituted 2-iminochromenes in aqueous media. A variety of 2-amino-4-(nitromethyl)-4H-chromene-3-carbonitriles has been synthesized in good yields. Polymeric microbeads were very durable and reused 5 times without a significant loss of activity. DFT calculations and experimental results revealed the significant role of π-π interactions as well as hydrogen bonding in the reaction mechanism.

  通过 N-甲基丙烯酰-L-(+)-色氨酸甲酯（MATrp）与乙二醇二甲基丙烯酸酯（EGDMA）的共聚反应得到了平均直径为 106-300 μm 的交联微珠[poly(EGDMA-MATrp)]，并成功地将其用作异相催化剂，用于硝基甲烷与取代的 2-亚氨基苯并吡喃在水介质中的共轭加成反应。该催化剂以良好的产率合成了多种 2-氨基-4-（硝基甲基）-4H-苯并吡喃-3-甲腈。聚合物微珠非常耐用，可重复使用 5 次，且活性不会明显降低。DFT 计算和实验结果表明，π-π 相互作用以及氢键在反应机理中发挥了重要作用。