N-isopropyl-2-oxo-2H-chromene-3-carboxamide | 1846-82-8

• 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: N-isopropyl-2-oxo-2H-chromene-3-carboxamide
• 英文别名: Coumarin-3-carbonsaeure-N-isopropylamid；2-oxo-N-propan-2-ylchromene-3-carboxamide
• CAS: 1846-82-8
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: DYFRHCOMCPYXPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  475.6±45.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  水杨醛 在 哌啶 、 4-二甲氨基吡啶 、 氯化亚砜 、 sodium hydroxide 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 N-isopropyl-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  New coumarin derivatives: Design, synthesis and use as inhibitors of hMAO

  摘要：

  A series new 2H-chromene-3-carboxamides (4a-4i) and S-2H-chromene-3-carbothioates (5j-5t) were synthesized and evaluated as monoamine oxidase A and B inhibitors. Among them, compound 5k (IC50=0.21μM, IC50 iproniazid=7.65μM) showed the most activity and higher MAO-B selectivity (189.2-fold vs 1-fold) with respect to the MAO-A isoform. The need to clarify at a 3D level some important molecular aspects of discussed SAR, we undertaked a number of docking simulations to better assess. The steric effect was analyzed interms of both posing and scoring by investigating the nature of the binding interactions. The docking results of active compound 5k with hMAO-B complex indicated that conserved residue ILE 199 was important for ligand binding via Sigma-Pi interaction.

  DOI：

  10.1016/j.bmc.2014.05.002

文献信息

• An efficient three-component synthesis of coumarin-3-carbamides by use of Ni–NiO nanoparticles as magnetically separable catalyst
  作者：Nayim Sepay、Chayan Guha、Arpan Kool、Asok K. Mallik

  DOI：10.1039/c5ra13932e

  日期：——

  An efficient and ecofriendly synthesis of coumarin-3-carbamides has been developed by a three-component reaction of 2-hydroxybenzaldehydes, aliphatic amines (p-/s-) and diethyl malonate using Ni–NiO nanoparticles as catalyst.

  使用Ni-NiO纳米颗粒作为催化剂，通过2-羟基苯甲醛、脂肪胺（p-/s-）和二乙基丙二酸酯的三组分反应，开发了一种高效、环保的香豆素-3-氨基甲酰化合物的合成方法。
• Novel Functional Peptide Nucleic Acid Monomer and Process for Producing the Same
  申请人：Ikeda Hisafumi

  公开号：US20080138817A1

  公开（公告）日：2008-06-12

  A compound represented by general formula (I) below; (in the formula, A denotes B denotes R denotes H, NO 2 , NH 2 , NHCbz, Br, F, Cl or SO 3 Na 2 , and n is an integer of 1 to 4 ), and a process for producing the above compound characterised in that it includes a reaction between an activated ester and a t-butoxycarbonylaminoethylamine or an ω-amino acid derivative.

  以下是一种由通式（I）表示的化合物；（在公式中，A代表B代表R代表H，NO2，NH2，NHCbz，Br，F，Cl或SO3Na2，n是1到4的整数），以及一种生产上述化合物的过程，其特征在于它包括激活酯和t-丁氧羰基氨乙胺或ω-氨基酸衍生物之间的反应。
• Piperidine-Iodine as Efficient Dual Catalyst for the One-Pot, Three-Component Synthesis of Coumarin-3-Carboxamides
  作者：Manuel Velasco、Nancy Romero-Ceronio、Rosalía Torralba、Oswaldo Hernández Abreu、Miguel A. Vilchis-Reyes、Erika Alarcón-Matus、Erika M. Ramos-Rivera、David M. Aparicio、Jacqueline Jiménez、Eric Aguilar García、David Cruz Cruz、Clarisa Villegas Gómez、Cuauhtémoc Alvarado

  DOI：10.3390/molecules27144659

  日期：——

  efficient one-pot, three-component synthetic method for the preparation of coumarin-3-carboxamides was carried out by the reaction of salicylaldehyde, aliphatic primary/secondary amines, and diethylmalonate. The protocol employs piperidine-iodine as a dual system catalyst and ethanol, a green solvent. The main advantages of this approach are that it is a metal-free and clean reaction, has low catalyst loading

  通过水杨醛、脂肪族伯/仲胺和丙二酸二乙酯的反应，进行了一种简单、高效的一锅三组分合成香豆素-3-羧酰胺的制备方法。该协议采用哌啶碘作为双系统催化剂和乙醇，一种绿色溶剂。这种方法的主要优点是它是一种无金属且清洁的反应，催化剂负载量低，并且不需要繁琐的后处理。
• US7282575B2
  申请人：——

  公开号：US7282575B2

  公开（公告）日：2007-10-16