4-hydroxy-3-(phenyl(piperidin-1-yl) methyl)-2H-chromen-2-one | 1330776-85-6

• 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-(phenyl(piperidin-1-yl) methyl)-2H-chromen-2-one
• 英文别名: 4-Hydroxy-3-[phenyl(piperidin-1-yl)methyl]-2h-chromen-2-one；4-hydroxy-3-[phenyl(piperidin-1-yl)methyl]chromen-2-one
• CAS: 1330776-85-6
• 化学式: C₂₁H₂₁NO₃
• 分子量: 335.403
• InChiKey: XQGCRRWXRDJPMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 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：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  哌啶 、 4-羟基香豆素 、 苯甲醛 在 magnetic sulfated zirconia nanocatalyst 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以87%的产率得到4-hydroxy-3-(phenyl(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

• An efficient non-ionic surfactant catalyzed multicomponent synthesis of novel benzylamino coumarin derivative via Mannich type reaction in aqueous media
  作者：Atul Kumar、Maneesh Kumar Gupta、Mukesh Kumar

  DOI：10.1016/j.tetlet.2011.06.040

  日期：2011.8

  An efficient non-ionic surfactant catalyzed multicomponent synthesis of novel benzylamino coumarin derivatives has been developed from secondary amines, aromatic aldehyde, and 4-hydroxy coumarin via Mannich type reaction in aqueous media. In this Mannich type reaction, surfactant forms stable colloidal medium to stabilize iminium ion which undergoes nucleophilic addition of 4-hydroxy coumarin to give

  已经通过仲胺，芳族醛和4-羟基香豆素在水介质中通过曼尼希型反应开发了一种有效的非离子表面活性剂催化的多组分合成新型苄基氨基香豆素衍生物的方法。在该曼尼希型反应中，表面活性剂形成稳定的胶体介质以稳定亚胺离子，该亚胺离子经过亲核加成4-羟基香豆素以非常好的收率得到苄基氨基香豆素。
• 3-Methylene-2,4-chromandione in situ trapping: introducing molecular diversity on 4-hydroxycoumarin
  作者：Adrien Montagut-Romans、Manon Boulven、Marc Lemaire、Florence Popowycz

  DOI：10.1039/c5ra22440c

  日期：——

  3-Methylene-2,4-chromandione trapped in a solid-state stable Mannich adduct, is released in solution.

  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。
• Development of novel ferrocene‐based MNP and its catalytic activity investigation in the synthesis of 3‐amino benzyl‐4‐hydroxycoumarin derivatives
  作者：Leila Pakjo、Shabnam Rahimpour、Reza Teimuri‐Mofrad

  DOI：10.1002/aoc.7176

  日期：2023.8

  magnetic nanoparticle were tested in the one-pot synthesis of hydroxycoumarin derivatives through the three-component reaction (t-CR) between 4-hydroxycoumarin, various aromatic aldehydes, and secondary amines at room temperature. Based on the obtained results, the prepared nano-catalyst has progressed through a t-CR due to the presence of acidic and basic segments in its structure. The short reaction time

  在本研究中，二氧化硅涂覆的 Fe 3 O 4负载纳米磁性双乙基二茂铁离子液体（IL） ，[Fe 3 O 4 @SiO 2 @CH 2 } 3 -咪唑鎓-FcH 2 PO 4}]，是使用简单的化学共沉淀程序设计和合成的新型催化剂。通过使用 EDX、FE-SEM、XRD 和 FT-IR 技术对合成的纳米颗粒进行了鉴定。通过室温下4-羟基香豆素、各种芳香醛和仲胺之间的三组分反应（t-CR），测试了新型磁性纳米粒子在羟基香豆素衍生物的一锅合成中的催化活性。根据所获得的结果，由于其结构中存在酸性和碱性链段，所制备的纳米催化剂已通过t-CR进行了发展。新型合成纳米磁性催化剂具有反应时间短、产率高、环境友好、易于后处理等优点。
• 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.
• 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.