N,N-dimethyl-2-oxo-2H-chromene-3-carboxamide | 1846-89-5

• 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: N,N-dimethyl-2-oxo-2H-chromene-3-carboxamide
• 英文别名: 2H-1-Benzopyran-3-carboxamide, N,N-dimethyl-2-oxo-；N,N-dimethyl-2-oxochromene-3-carboxamide
• CAS: 1846-89-5
• 化学式: C₁₂H₁₁NO₃
• mdl: MFCD01181344
• 分子量: 217.224
• InChiKey: SUTFHRPLCUZXQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-2-oxo-2H-chromene-3-carboxamide 在 乙醇 、 铂 作用下， 生成 2-oxo-chroman-3-carboxylic acid dimethylamide
  参考文献：
  名称：

  Ito, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 149

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N,N’,N’-四甲基丙二酰胺 、 水杨醛 生成 N,N-dimethyl-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  DE679388

  摘要：

  公开号：

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。
• A New and Efficient Method for the Synthesis of 3,4-Disubstituted Pyrrolidine-2,5-diones
  作者：Eleonora D. Ilieva、Nevena I. Petkova、Rositca D. Nikolova

  DOI：10.3390/molecules17054936

  日期：——

  A newly found reaction for the synthesis of 3,4-disubstituted 1-hydroxy-pyrrolidine-2,5-diones from 3-substituted coumarins and nitromethane has been elaborated. The reaction involved a simple and convenient experimental procedure. The applicability of the rearrangement reaction is determined.

  一个新发现的用于从 3-取代香豆素和硝基甲烷合成 3,4-二取代 1-羟基-吡咯烷-2,5-二酮的反应已经详细说明。该反应涉及简单方便的实验程序。确定重排反应的适用性。
• Synthesis of benzopyranopyrrolidines via 1,3-dipolar cycloaddition of nonstabilized azomethine ylides with 3-substituted coumarins
  作者：Vladimir S. Moshkin、Vyacheslav Ya. Sosnovskikh、Gerd-Volker Röschenthaler

  DOI：10.1016/j.tet.2013.05.018

  日期：2013.7

  three-component reaction of 3-substituted coumarins with N-alkyl-α-amino acids and aldehydes gave 1-benzopyrano[3,4-c]pyrrolidines as a result of a 1,3-dipolar cycloaddition of an intermediate nonstabilized azomethine ylide at the double bond of the coumarin system in moderate to good yields. In most cases, high regio- and stereo-selectivity of the [3+2] cycloaddition was observed.

  3-取代的香豆素与N-烷基-α-氨基酸和醛类的三组分反应产生了1-苯并吡喃并[3,4- c ]吡咯烷，这是由于中间体非稳定的甲亚胺基内酯的1,3-偶极环加成反应的结果。在香豆素系统的双键上以中等至良好的产率。在大多数情况下，观察到[3 + 2]环加成反应的高区域选择性和立体选择性。
• 1,3-Dipolar cycloadditions of nonstabilised azomethine ylides at 3-substituted coumarins: synthesis of 1-benzopyrano[3,4-c]pyrrolidines
  作者：Vladimir S. Moshkin、Vyacheslav Ya. Sosnovskikh、Pavel A. Slepukhin、Gerd-Volker Röschenthaler

  DOI：10.1016/j.mencom.2012.01.011

  日期：2012.1

  Reaction of 3-substituted coumarins with N-alkyl-α-amino acids and aldehydes proceeds regio- and stereoselectively to give 1-benzopyrano[3,4-c]pyrrolidines as a result of 1,3-dipolar cycloaddition of the intermediate azomethine ylides at the Δ3-bond of the coumarins.

  3-取代的香豆素与N-烷基-α-氨基酸和醛的反应在区域和立体上进行，得到1-苯并吡喃并[3,4-c]吡咯烷，这是中间体偶氮甲亚胺的1,3-偶极环加成反应的结果在香豆素的Δ3键上
• 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。