2-amino-4-(2-chlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-amino-4-(2-chlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid ethyl ester
• 英文别名: ethyl 2-amino-4-(2-chlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate；ethyl 2-amino-4-(2-chlorophenyl)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3-carboxylate
• 化学式: C₂₀H₂₂ClNO₄
• 分子量: 375.852
• InChiKey: SWYXCLYZGVYLPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯苯甲醛 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 2-amino-4-(2-chlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Substituted Tetrahydrochromenes by the Reactions of α,β-Unsaturated Cyanoesters with Dimedone/1,3-Cyclohexanedione

  摘要：

  Ethyl esters of 2-cyano-3-arylacrylic acid 1a-d (a=4-CH3-C6H4-, b=4-N(CH3)(2)-C6H4-, c=2-CH3O-C6H4-, d=2-Cl-C6H4-) reacted with 5,5-dimethyl-1,3-cyclohexanedione (2p, Y=CH3), and 1e-g (e=4-CH3-C6H4-, f=2-CH3O-C6H4-, g=2-Cl-C6H4-) reacted with 1,3-cyclohexanedione (2q, Y=H) in the presence of alcoholic sodium ethoxide to give the corresponding ethyl esters of 2-amino-7,7-dimethyl-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid 4a-d and 2-amino-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid 4e-g. The structures of the compounds 4a-g were confirmed by their ultraviolet, infrared, H-1 NMR, C-13 NMR, and mass spectral data and elemental analyses.

  DOI：

  10.1080/00397911.2010.515346

文献信息

• Catalyst Free One-pot Three-component Synthesis of 2-Amino-4Hchromene Derivatives in Aqueous Deep Eutectic Mixture at Room Temperature
  作者：Atul Chaskar

  DOI：10.2174/1570178611666140210213413

  日期：2014.4

  Multifunctional chromenes have been efficiently synthesized in aqueous medium at room temperature using deep eutectic mixture of choline chloride:urea. In this one-pot synthesis, the benzylidenemalononitrile firstly formed by Knoevenagel condensation of aldehyde and malononitrile eventually underwent Michael addition-cyclization with dimedone and offered the chromenes in good to excellent yield.

  在室温下的水相介质中，通过氯化胆碱与尿素的低共熔混合物，已高效合成了多功能色烯类化合物。在这一步法合成过程中，首先由醛与丙二腈的Knoevenagel缩合反应生成苄叉丙二腈，进而通过与二甲双酮的迈克尔加成-环化反应，以良好至优异的产率获得了色烯类化合物。
• A nano-organo catalyzed route towards the efficient synthesis of benzo[b]pyran derivatives under ultrasonic irradiation
  作者：Ridaphun Nongrum、Geetmani Singh Nongthombam、Mattilang Kharkongor、Jims World Star Rani、Noimur Rahman、Chingrishon Kathing、Bekington Myrboh、Rishanlang Nongkhlaw

  DOI：10.1039/c6ra24108e

  日期：——

  reaction time and use of green solvents. Ultrasound energy has been meticulously exploited for the synthesis of a nano-organocatalyst as well as for the preparation of several benzo[b]pyran derivatives. The biological activity of the synthesized benzo[b]pyrans were investigated and one of the derivatives was found to demonstrate profound activity in suppressing the side-effects of chlorpyrifos, an insecticide

  本文报道了在超声条件下由维生素B 1官能化的Fe 2 O 3 @SiO 2 NPs催化的高效一锅合成苯并[ b ]吡喃。纳米有机催化剂的合成和表征通过FT-IR，TEM，EDS，粉末X射线衍射，等等若干苯并[ b以令人满意的产率制备了]吡喃衍生物，并且磁性回收和再循环了纳米催化剂。该方案的显着特征包括方便的后处理程序，温和的反应条件，容易的催化剂回收，较短的反应时间和绿色溶剂的使用。超声波能量已经被精心开发用于合成纳米有机催化剂以及制备几种苯并[ b ]吡喃衍生物。合成的苯并[生物活性b ]吡喃进行了调查和衍生物中的一种被发现表现出在抑制毒死蜱的副作用，对的外部鳃的形态杀虫剂深刻活性黑眶蟾蜍蝌蚪。
• 1,4-Diazabicyclo[2.2.2]octane as an Efficient Catalyst for a Clean, One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives via Multicomponent Reaction in Aqueous Media
  作者：Daryoush Tahmassebi、Jessica A. Bryson、Sophia I. Binz

  DOI：10.1080/00397911.2010.515345

  日期：2011.9.15

  mild and efficient catalyst for the synthesis of various tetrahydrobenzo[b]pyran derivatives via a one-pot, three component condensation of aromatic aldehydes, dimedone, and active methylene compounds. This method provides several advantages: a simple workup procedure, environmental friendliness, neutral conditions, and good yields. In addition, water or 50% aqueous ethanol was chosen as a green solvent

  摘要 1,4-二氮杂双环[2.2.2]辛烷 (DABCO) 已被用作一种温和高效的催化剂，通过芳香醛、二甲酮、和活性亚甲基化合物。这种方法提供了几个优点：简单的后处理程序、环境友好、中性条件和良好的收率。此外，选择水或 50% 乙醇水溶液作为绿色溶剂。
• Synthesis and applications of CoFe₂O₄nanoparticles for multicomponent reactions
  作者：Jaspreet Kaur Rajput、Gagandeep Kaur

  DOI：10.1039/c3cy00594a

  日期：——

  An efficient, simple, green protocol is developed for the synthesis of 2-amino-4-(phenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile derivatives and 2,2′-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives in the presence of CoFe2O4 nanoparticles in aqueous ethanol medium. CoFe2O4 nanoparticles have been synthesised by a co-precipitation method followed by

  开发了一种高效，简单的绿色方案，用于合成2-氨基-4-（苯基）-5,6,7,8-四氢-7,7-二甲基-5-氧代-4 H-色烯-3-乙醇水溶液中在CoFe 2 O 4纳米粒子存在下，腈衍生物和2,2'-芳基亚甲基双（3-羟基-5,5-二甲基-2-环己烯-1-酮）衍生物。CoFe 2 O 4纳米颗粒已经通过共沉淀法随后超声合成。合成的CoFe 2 O 4纳米颗粒具有高表面积（140.9 m 2 g -1）和小尺寸（2-8 nm）。当使用含水介质时，本发明的催化方法提供了可持续性，通过提供高产率的产物，反应在短的反应时间内进行，并且由于催化剂便宜并且可以从反应混合物中回收，因此是经济的。回收的催化剂可以用于多个循环而不会损失很多活性。该方案是绿色的，因为未使用色谱技术，因此消除了使用有害有机溶剂的可能性。CoFe 2 O 4成为一种高效，可持续，稳定和可回收的催化剂。
• Ionic Liquid Promoted Knoevenagel and Michael Reactions
  作者：Xuesen Fan、Xueyuan Hu、Xinying Zhang、Jianji Wang

  DOI：10.1071/ch04060

  日期：——

  The utilization of the ionic liquid [bmim][BF4] as both reaction medium and promoter for the Knoevenagel condensation and Michael addition reactions is described in this paper. Through these reactions, several useful electrophilic alkenes and chromene derivatives are obtained in high yields. The advantages of these two novel procedures include their environmentally benign nature, atom economy, simple operation process, and mild reaction conditions.

  本文介绍了利用离子液体 [bmim][BF4]作为反应介质和促进剂来进行克诺文纳格尔缩合反应和迈克尔加成反应的方法。通过这些反应，可以高产率地获得多种有用的亲电烯和色烯衍生物。这两种新方法的优点包括对环境无害、原子经济、操作过程简单和反应条件温和。