2-amino-4-(4-N,N-dimethylaminophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid ethyl ester | 401824-53-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-amino-4-(4-N,N-dimethylaminophenyl)-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-[4-(dimethylamino)phenyl]-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3-carboxylate
• CAS: 401824-53-1
• 化学式: C₂₂H₂₈N₂O₄
• 分子量: 384.475
• InChiKey: FYGKKWNXKYNZFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氰基-3-[4-(二甲基氨基)苯基]丙烯酸乙酯 、 5,5-二甲基-1,3-环己二酮 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以70%的产率得到2-amino-4-(4-N,N-dimethylaminophenyl)-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

• Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water
  作者：Hamzeh Kiyani、Fatemeh Ghorbani

  DOI：10.1007/s11164-014-1863-7

  日期：2015.10

  A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the three-component tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50 °C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in α,β-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyran-annulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up.

  合成了一系列4H-克罗梅、苯并克罗梅、4,5-二氢吡喃[3,2-c]克罗梅、4H-吡喃-3-羧酸盐以及3,4-二取代的异噁唑-5(4H)-酮，采用了氢钾邻苯二甲酸盐（KHP）作为廉价的商业可得催化剂，得到了高产率。研究发现，这种三组分串联反应使得在50°C的水相中合成了吡喃环接合的杂环化合物。3,4-二取代的异噁唑-5(4H)-酮是在室温下使用10 mol% KHP水相合成的。此外，在存在5 mol% KHP的情况下，采用含亚甲基的化合物（如马来腈或乙基氰乙酸酯）与芳香醛的反应，得到了α,β-不饱和腈。该方法是一种简单易行的合成多种吡喃环接合化合物、含异噁唑-5(4H)-酮的杂环化合物和Knoevenagel加成物的直截了当的方法。该反应安全、条件温和且环境友好。其他显著优点包括催化剂的重复使用、不使用有害有机溶剂以及简便的后处理。
• Preparation of nanomagnetic alginate modified by histidine as an antibacterial agent and a reusable green catalyst for the three-component synthesis of 2-amino-4H-chromenes and tetrahydropyrimidines
  作者：Moghadaseh Keshvari Kenari、Sakineh Asghari、Behrooz Maleki、Mojtaba Mohseni

  DOI：10.1007/s11164-023-05165-6

  日期：2024.2

  acid–base nanocatalyst (MNPs@Alg-Pr-His) was synthesized using available materials (nanomagnetic alginate core and histidine) via a facile strategy. After characterization, its efficiency was investigated in the synthesis of 2-amino-4H-chromene and 1,2,3,6-tetrahydropyrimidine derivatives. This nanobiocatalyst showed remarkable catalytic efficiency in both reactions (the reaction yields for the first

  使用现有材料（纳米磁性藻酸盐核心和组氨酸）通过简单的策略合成了一种新型酸碱纳米催化剂（MNPs@Alg-Pr-His）。经过表征后，研究了其在2-氨基-4H-色烯和1,2,3,6-四氢嘧啶衍生物合成中的效率。这种纳米生物催化剂在两个反应中都表现出显着的催化效率（第一个反应的反应产率：89-96%，第二个反应的反应产率：68-85%）。该催化剂可重复使用和回收，并且在五次运行后仍然表现出良好的活性。通过纸片扩散法评价组氨酸、藻酸盐和MNPs@Alg-Pr-His对革兰氏阳性菌（金黄色葡萄球菌）和革兰氏阴性菌（大肠杆菌）的抗菌效果。值得注意的是，与组氨酸和藻酸盐不同，MNPs@Alg-Pr-His 对革兰氏阴性菌 (28.0 ± 1.4) 的抗菌活性高于对革兰氏阳性菌 (19.0 ± 1.4) 的抗菌活性。 图形概要
• Green one-pot synthesis of 2-amino-4H-pyranes catalyzed by copper–arginine complex decorated on nano-NaY zeolite
  作者：Farzaneh Khoshlahjeh、Sakineh Asghari、Ghasem Firouzzadeh Pasha

  DOI：10.1007/s11164-024-05262-0

  日期：2024.5

  without a noticeable decrease in activity. The nanocatalyst activity was investigated in synthesizing 2-amino-4H-pyrans. These compounds were synthesized in good to high yields (72–95%) in ethanol as a green solvent at room temperature within 1 h. The structure of the products was identified and confirmed by measuring the melting points and their 1H NMR, 13C NMR, and FT-IR spectral data. Graphical abstract

  本研究通过用精氨酸对NaY纳米沸石进行功能化，然后在其表面固定铜金属离子，制备了一种新型多相纳米催化剂Cu@Zeo-Arg。合成的纳米催化剂的形成已通过各种分析（例如 TGA、FT-IR、CHN、BET、XRD、SEM、ICP、DLS 和 EDS 图谱）进行了彻底研究和证实。所制备的纳米催化剂具有易分离、稳定性高、可回收、可重复使用等独特优点。此外，催化剂被回收并重复使用长达七次连续运行，活性没有明显下降。研究了纳米催化剂在合成2-氨基-4H-吡喃中的活性。这些化合物在乙醇作为绿色溶剂中在室温下 1 小时内以良好到高产率 (72-95%) 合成。通过测量熔点及其1 H NMR、13 C NMR 和 FT-IR 光谱数据来鉴定和确认产物的结构。 图形概要
• Facile and Efficient Access to Tetrahydrobenzo[b]pyrans Catalyzed by N,N-Dimethylbenzylamine
  作者：Hamzeh Kiyani、Mozhgan Sadat Jalali

  DOI：10.3987/com-15-13360

  日期：——

  The N,N-dimethylbenzylamine (DMBA) has been used as an efficient, inexpensive, and commercially available organocatalyst for the one-pot, three-component synthesis of tetrahydrobenzo[b]pyrans in good to high yields. It was found that the one-pot Knoevenagel-Michael-Thorpe-Ziegler cyclization sequence of dimedone, malononitrile/ethyl cyanoacetate, and various aldehydes was efficiently implemented in ethanol at 45 degrees C. This procedure offers attractive several features: mild reaction conditions, use of ethanol as a green solvent, reusability the reaction media, shorter reaction times, and the ease of the work-up.
• Synthesis of Substituted Tetrahydrochromenes by the Reactions of α,β-Unsaturated Cyanoesters with Dimedone/1,3-Cyclohexanedione
  作者：M. Giasuddin Ahmed、U. K. R. Romman、Kawsari Akhter、Khorshada Jahan、M. Nazmul Hasan Bhuiyan、M. Ershad Halim

  DOI：10.1080/00397911.2010.515346

  日期：2011.10

  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.