4-hydroxy-3-[(morpholin-4-yl)(phenyl)methyl]-2H-chromen-2-one | 1380515-01-4

• 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-[(morpholin-4-yl)(phenyl)methyl]-2H-chromen-2-one
• 英文别名: 4-hydroxy-3-(morpholino(phenyl)methyl)-2H-chromen-2-one；4-hydroxy-3-(morpholin-4-yl-phenyl-methyl)-chromen-2-one；3-[(Morpholin-4-yl)phenylmethyl]-4-hydroxycoumarin；4-hydroxy-3-[morpholin-4-yl(phenyl)methyl]chromen-2-one
• CAS: 1380515-01-4
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: DXCJPAUVPHSEPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吗啉 、 4-羟基香豆素 、 苯甲醛 在 barium silicate 作用下， 以 水 为溶剂， 以93 %的产率得到4-hydroxy-3-[(morpholin-4-yl)(phenyl)methyl]-2H-chromen-2-one
  参考文献：
  名称：

  硅酸钡纳米颗粒，一锅绿色合成α-苄基氨基香豆素衍生物作为潜在化疗药物的高效催化剂

  摘要：

  通过芳香醛、胺和 4-羟基香豆素的一锅三组分缩合，描述了一种新的、简单的、高效的合成 α-苄基氨基香豆素及其衍生物 ( 1-24 ) 的方法。 ：水作为溶剂，BaSiO 3纳米粒子作为催化剂。BaSiO 3纳米粒子和所有合成的衍生物通过多种方法进行表征，包括：XRD、NMR 和 FE-SEM。与文献中的其他方法相比，该方法产量更高，成本更低，并且更环保。计算机模拟对所有合成的化合物进行了理化和药代动力学分析，表明这些 α-苄基氨基香豆素将成为未来化疗药物开发的有效支架。

  DOI：

  10.1039/d3ra00796k

文献信息

• 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。
• 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.