4-hydroxy-3-((4-nitrophenyl)(pyrrolidin-1-yl)methyl)-2H-chromen-2-one | 1380515-10-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-hydroxy-3-((4-nitrophenyl)(pyrrolidin-1-yl)methyl)-2H-chromen-2-one
• 英文别名: 4-Hydroxy-3-[(4-nitrophenyl)-pyrrolidin-1-ylmethyl]chromen-2-one
• CAS: 1380515-10-5
• 化学式: C₂₀H₁₈N₂O₅
• 分子量: 366.373
• InChiKey: MKVNDBFVOSCWEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-((4-nitrophenyl)(pyrrolidin-1-yl)methyl)-2H-chromen-2-one 、 丙二腈 以 乙腈 为溶剂， 反应 3.0h， 以72%的产率得到2-amino-4-(4-nitrophenyl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile
  参考文献：
  名称：

  3-Methylene-2,4-chromandione in situ trapping: introducing molecular diversity on 4-hydroxycoumarin

  摘要：

  3-亚甲基-2,4-色酮在固态稳定的Mannich加合物中被困，溶液中释放。

  DOI：

  10.1039/c5ra22440c
• 作为产物：
  描述：

  四氢吡咯 、 4-羟基香豆素 、 对硝基苯乙酮 以 乙腈 为溶剂， 反应 2.0h， 生成 4-hydroxy-3-((4-nitrophenyl)(pyrrolidin-1-yl)methyl)-2H-chromen-2-one
  参考文献：
  名称：

  不对称双（4-羟基香豆素-3-基）甲烷的一锅法合成

  摘要：

  不对称双 (4-羟基香豆素-3-基) 甲烷衍生物已从 4-羟基香豆素、醛和仲胺通过 3-(氨基烷基)-4-羟基香豆素中间体合成，然后进行取代。

  DOI：

  10.1055/s-0036-1589065

文献信息

• Fe ₃ O ₄ @ZrO ₂ /SO ₄ ^2‐ : A recyclable magnetic heterogeneous nanocatalyst for synthesis of β‐amino carbonyl derivatives and synthesis of benzylamino coumarin derivatives through Mannich reaction
  作者：Hossein Ghafuri、Behnaz Ghorbani、Afsaneh Rashidizadeh、Majid Talebi、Mahdi Roshani

  DOI：10.1002/aoc.4147

  日期：2018.3

  developed an effective protocol for the synthesis of β‐amino carbonyl compounds and synthesis of benzylamino coumarin derivatives through Mannich type reaction in high yields. Fe3O4@ZrO2/SO42‐ was employed as an effective heterogeneous nanocatalyst for the Mannich reaction. This research consists of two sections. In first section, β‐amino carbonyl derivatives were synthesized under solvent‐free condition

  在当前的工作中，我们开发了一种有效的方案，用于通过Mannich型反应以高收率合成β-氨基羰基化合物和合成苄基氨基香豆素衍生物。Fe 3 O 4 @ZrO 2 / SO 4 2‐将其用作曼尼希反应的有效多相纳米催化剂。本研究分为两个部分。在第一部分中，在无溶剂条件下合成了β-氨基羰基衍生物。在另一部分中，在室温下合成苄氨基香豆素化合物。本方法具有许多优点，例如反应时间短，成本低，易于后处理，反应条件温和，收率高，催化剂的回收率和可重复使用性好，而活性没有明显损失。
• β-Cyclodextrin Based Nanosponge as a Biodegradable Porous Three-Dimensional Nanocatalyst in the One-Pot Synthesis of N- Containing Organic Scaffolds
  作者：N. Eskandari Sabzi、A. R. Kiasat

  DOI：10.1007/s10562-018-2484-3

  日期：2018.9

  porous three-dimensional nanocatalyst in the one-pot three component condensations of various aromatic aldehydes with activated methylene compounds such as dimedone, thiobarbituric acid, 4-hydroxycoumarin, 4-hydroxy-6-methyl-2-pyrone and nucleophiles including indole and amines. This nanosponge catalyst afforded the privileged N- containing organic scaffolds as key intermediates in pharmaceutical chemistry

  本研究背后的动机是开发具有微小网状结构的基于β-环糊精的纳米海绵作为多孔三维纳米催化剂在各种芳香醛与活化的亚甲基化合物如二甲酮的一锅三组分缩合反应中的应用。 、硫代巴比妥酸、4-羟基香豆素、4-羟基-6-甲基-2-吡喃酮和亲核试剂，包括吲哚和胺。这种纳米海绵催化剂在很短的反应时间内提供了作为药物化学关键中间体的特权含氮有机支架。
• Nano crystalline ZnO: a competent and reusable catalyst for one pot synthesis of novel benzylamino coumarin derivatives in aqueous media
  作者：Partha Pratim Ghosh、Asish R. Das

  DOI：10.1016/j.tetlet.2012.04.033

  日期：2012.6

  A green, efficient and facile protocol was developed for the synthesis of a series of benzylamino coumarin derivatives by the reaction of 4-hydroxycoumarin, cyclic secondary amine, and aromatic aldehyde in aqueous media in the presence of nano crystalline ZnO at room temperature. A wide range of functional groups were tolerated in the developed protocol. The target molecules were obtained in good to excellent yield applying the current method. The nano crystalline ZnO can be recycled five times with almost the same catalytic activity. (C) 2012 Elsevier Ltd. All rights reserved.
• InCl3 catalyzed three-component synthesis of α-benzylamino coumarins and diketones
  作者：Pallavi Rao、Saidulu Konda、Javed Iqbal、Srinivas Oruganti

  DOI：10.1016/j.tetlet.2012.07.098

  日期：2012.9

  A convenient and practical InCl3 catalyzed three-component reaction of 4-hydroxy coumarin/1,3 diones, aromatic aldehyde, and secondary amine for the synthesis of alpha-benzylamino coumarins and diketones in good yields has been reported. (c) 2012 Elsevier Ltd. All rights reserved.