methyl 2-amino-7,7-dimethyl-4-(4-methylphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate

• 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: methyl 2-amino-7,7-dimethyl-4-(4-methylphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate
• 英文别名: methyl 2-amino-7,7-dimethyl-4-(4-methylphenyl)-5-oxo-6,8-dihydro-4H-chromene-3-carboxylate
• 化学式: C₂₀H₂₃NO₄
• 分子量: 341.407
• InChiKey: KOUZONRKPDKPHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  3
• 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：

  4-乙酰基-3-苄基-4H-1,4-苯并噻嗪 、 5,5-二甲基-1,3-环己二酮 在 aluminum oxide 、 potassium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到methyl 2-amino-7,7-dimethyl-4-(4-methylphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate
  参考文献：
  名称：

  A Convenient Synthesis of 5-Oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran Derivatives Catalyzed by KF-Alumina

  摘要：

  A series of 5-oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran derivatives were prepared by the reaction of arylmethylidenemalononitriles or 2-cyano-3-aryl-1-acrylate with 5,5-dimethyl- 1, 3-cyclohexanedione (dimedone) in DMF at room temperature catalyzed by KF-alumina. The structure of the product was confirmed by X-ray analysis.

  DOI：

  10.1081/scc-120015567

文献信息

• Uncatalyzed Reactions in Aqueous Media: Three-Component, One-Pot, Clean Synthesis of Tetrahydrobenzo[b]pyran Derivatives
  作者：Sunita B. Bandgar、Babasaheb P. Bandgar、Balaji L. Korbad、Jalinder V. Totre、Sachin Patil

  DOI：10.1071/ch06461

  日期：——

  The synthesis of various tetrahydrobenzo[b]pyran derivatives has been carried out by means of an uncatalyzed, three-component, one-pot clean condensation of aromatic aldehydes, reactive methylene compounds, and dimidone in aqueous medium. Simple workup, and mild and neutral conditions that give quantitative yields of products in pure form, are the attractive features of this method.

  各种四氢苯并[b]吡喃衍生物的合成是通过芳香醛、反应性亚甲基化合物和二米酮在水介质中的非催化、三组分、一锅清洁缩合进行的。简单的后处理，温和和中性的条件，可以定量获得纯产品的产量，是这种方法的吸引人的特点。
• One‐Pot Synthesis of 2‐Amino‐4‐aryl‐3‐carbalkoxy‐7,7‐dimethyl‐5,6,7,8‐tetrahydrobenzo[<i>b</i>]pyran Derivatives Catalyzed by KF/Basic Al₂O₃Under Ultrasound Irradiation
  作者：Ji‐Tai Li、Wen‐Zhi Xu、Li‐Chao Yang、Tong‐Shuang Li

  DOI：10.1081/scc-200043233

  日期：2004.1

  Synthesis of 2-amino-4-aryl-3-carbalkoxy-7,7-dimethyl-5-oxo-5,6,7,8-tertrahydrobenzo[b]pyran derivatives was carried out in 81-98% yields by one-pot condensation of aromatic aldehydes with cyanoacetic esters and 5,5-dimethyl-1,3-cyclohexanedione catalyzed by KF/basic Al2O3 at room temperature under ultrasound irradiation.
• Diammonium Hydrogen Phosphate: An Efficient and Versatile Catalyst for the One‐Pot Synthesis of Tetrahydrobenzo[<i>b</i>]pyran Derivatives in Aqueous Media
  作者：Saeed Balalaie、Morteza Bararjanian、Masoumeh Sheikh‐Ahmadi、Shohreh Hekmat、Peyman Salehi

  DOI：10.1080/00397910701196579

  日期：2007.4.1

  Diammonium hydrogen phosphate was used as a mild, efficient, neutral, and cheap catalyst for the synthesis of various 4H-benzo[b]pyran derivatives via a one-pot, three-component condensation of aromatic aldehydes, active methylene compounds, and dimedone in aqueous media.
• Efficient Synthesis of Tetrahydrobenzo[<i>b</i>]pyrans under Solvent‐Free Conditions at Room Temperature
  作者：Liangce Rong、Xiaoyue Li、Haiying Wang、Daqing Shi、Shujiang Tu、Qiya Zhuang

  DOI：10.1080/00397910600640230

  日期：2006.8

  A range of tetrahydrobenzo[b]pyrans have been synthesized in very good yields under solvent-free conditions by grinding alpha-cyanocinnamonitrils or beta-cyano-beta-carbethoxy styrene and 5,5-dimethyl-1,3-cyclohexanedione in the presence of TEBA as catalyst. The short reaction time, cleaner reaction, and easy workup make this protocol practical and economically attractive.
• A Convenient Synthesis of 5-Oxo-5,6,7,8-tetrahydro-4<b><i>H</i></b>-benzo-[b]-pyran Derivatives Catalyzed by KF-Alumina
  作者：Xiang-Shan Wang、Da-Qing Shi、Shu-Jiang Tu、Chang-Sheng Yao

  DOI：10.1081/scc-120015567

  日期：2003.3

  A series of 5-oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran derivatives were prepared by the reaction of arylmethylidenemalononitriles or 2-cyano-3-aryl-1-acrylate with 5,5-dimethyl- 1, 3-cyclohexanedione (dimedone) in DMF at room temperature catalyzed by KF-alumina. The structure of the product was confirmed by X-ray analysis.