2-Amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid methyl ester
• 英文别名: methyl 2-amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate；methyl 2-amino-7,7-dimethyl-5-oxo-4-phenyl-6,8-dihydro-4H-chromene-3-carboxylate
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: NBNOTWAEVQQITB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  苯甲醛 在 碳酸氢铵 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 2-Amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  杂合紫苏4H-吡喃的合成。对肝细胞癌HepG2 / C3A细胞系的细胞毒性评估

  摘要：

  通过结合多组分反应和铜催化的炔-叠氮化物环加成反应（CuAAC）的策略，直接合成了一系列15种新的perillyl-4 H-吡喃杂化物。含有炔部分的2-氨基-4 H-吡喃-3-腈是通过1,3-二羰基，炔丙氧基芳族醛和丙二腈或α-氰基乙酸乙酯之间的多组分反应制得的。炔烃衍生物通过铜催化的[3 + 2] Huisgen环加成反应顺序与紫苏叠氮化物组分反应。评价了杂交化合物对人肝癌HepG2 / C3A细胞系的抗增殖活性。

  DOI：

  10.1002/jhet.3977

文献信息

• Synthesis and X-ray crystal structures of polyfunctionalized 4H-chromene derivatives via tricomponent reaction with Knoevenagel adducts as intermediates in aqueous medium
  作者：Lucas Lima Zanin、David Esteban Quintero Jimenez、Matheus Pereira de Jesus、Luan Farinelli Diniz、Javier Ellena、André Luiz Meleiro Porto

  DOI：10.1016/j.molstruc.2020.129226

  日期：2021.1

  triethylamine as catalyst. Twenty 4H-chromene derivatives were synthesized with 50–95% yields from aromatic aldehydes, 5,5-dimethyl-1,3-cyclohexadione and malononitrile or methyl cyanoacetate, being further characterized by Fourier Transform Infrared and Nuclear Magnetic Resonance. We also report three crystal structures from the synthesized chromene derivatives, by single-crystal X-ray diffraction, showing

  摘要 Chromenes 及其衍生物是一类重要的化合物，以其生物学特性而闻名。在本研究中，描述了获得 4H-色烯衍生物的合成方法。研究了两种途径，第一种是使用 Knoevenagel 加合物作为试剂的双组分反应，第二种是使用一锅三组分反应，均在微波辐射下，使用 H2O 作为溶剂，三乙胺作为催化剂。从芳香醛、5,5-二甲基-1,3-环己二酮和丙二腈或氰基乙酸甲酯合成了 20 种 4H-色烯衍生物，产率 50-95%，进一步通过傅里叶变换红外和核磁共振进行表征。我们还通过单晶 X 射线衍射报告了合成色烯衍生物的三种晶体结构，
• 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.
• 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.