4-hydroxy-3-((4-nitrophenyl)(piperidin-1-yl)methyl)-2H-chromen-2-one | 1380515-08-1

• 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)(piperidin-1-yl)methyl)-2H-chromen-2-one
• 英文别名: 4-hydroxy-3-[(4-nitro-phenyl)-piperidin-1-yl-methyl]-chromen-2-one；4-Hydroxy-3-[(4-nitrophenyl)-piperidin-1-ylmethyl]chromen-2-one；4-hydroxy-3-[(4-nitrophenyl)-piperidin-1-ylmethyl]chromen-2-one
• CAS: 1380515-08-1
• 化学式: C₂₁H₂₀N₂O₅
• 分子量: 380.4
• InChiKey: JJJRWODOWSQGKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  哌啶 、 4-羟基香豆素 、 对硝基苯甲醛 在 magnetic sulfated zirconia nanocatalyst 作用下， 以 乙腈 为溶剂， 反应 0.2h， 以90%的产率得到4-hydroxy-3-((4-nitrophenyl)(piperidin-1-yl)methyl)-2H-chromen-2-one
  参考文献：
  名称：

  Fe3O4 @ ZrO2 / SO42-：一种可回收的磁性多相纳米催化剂，用于通过曼尼希反应合成β-氨基羰基衍生物和苄基氨基香豆素衍生物

  摘要：

  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。

  DOI：

  10.1002/aoc.4147

文献信息

• 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.
• One-pot three-component synthesis of 3-(α-aminobenzyl)-4-hydroxycoumarin derivatives using nanocrystalline TiO2 as reusable catalyst
  作者：J. N. Sangshetti、F. A. K. Khan、C. S. Kute、Z. Zaheer、R. Z. Ahmed

  DOI：10.1134/s107042801501011x

  日期：2015.1

  An efficient nanocrystalline TiO2-catalyzed one-pot synthesis of 3-[(piperidin-1-yl)phenylmethyl]- and 3-[(morpholin-4-yl)phenylmethyl]-4-hydroxycoumarins has been developed via three-component Mannich type condensation of 4-hydroxycoumarin with aromatic aldehydes and secondary amines (piperidine or morpholine) in ethanol at room temperature. The catalyst can be easily recovered and reused with almost the same catalytic activity. The proposed method is advantageous due to its simplicity, short reaction time, catalyst reusability, good to excellent yield, and clean and easy work-up.
• 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。