1228377-92-1 ((1,2-Ethanedione, 1-(4-morpholinyl)-2-(2-naphthalenyl)-)

快速询单

结构式：

1,2-Ethanedione, 1-(4-morpholinyl)-2-(2-naphthalenyl)-MOL文件

CAS号：

1228377-92-1

英文名称：

1,2-Ethanedione, 1-(4-morpholinyl)-2-(2-naphthalenyl)-

分子式：

C₁₆H₁₅NO₃

分子量：

269.295204401016

1,2-Ethanedione, 1-(4-morpholinyl)-2-(2-naphthalenyl)-(1228377-92-1)名称与标识符

名称

英文别名：

1-(4-Morpholinyl)-2-(2-naphthalenyl)-1,2-ethanedione;1-Morpholino-2-(naphthalen-2-yl)ethane-1,2-dione;

标识符

InChIKey：

MROADJBMULNWBV-UHFFFAOYSA-N

Inchi：

1S/C16H15NO3/c18-15(16(19)17-7-9-20-10-8-17)14-6-5-12-3-1-2-4-13(12)11-14/h1-6,11H,7-10H2

SMILES：

C1=CC2C=C(C=CC=2C=C1)C(C(=O)N1CCOCC1)=O

1,2-Ethanedione, 1-(4-morpholinyl)-2-(2-naphthalenyl)-(1228377-92-1)合成路线

合成路线：1 步

反应条件：

1.1R:Bu4N+ •HSO4-, C:Cu(OAc)2, S:MeCN, 6 h, 80°C

参考文献：

Copper-Catalyzed Transamidation of Unactivated Secondary Amides via C-H and C-N Bond Simultaneous Activations

By Lv, Cong et al, Journal of Organic Chemistry, 2023, 88(4), 2140-2157

合成路线：2 步

反应条件：

1.1R:t-BuOK, S:THF, 2 h, reflux; reflux → 0°C
1.2S:THF, 0°C → rt; 3 h, rt
2.1R:O2, C:Cu, C:C5H5N, S:Dioxane, 12 h, 70°C, 1 atm

参考文献：

Copper-Catalyzed Synthesis of α-Keto Amides from Sulfoxonium Ylides

By Wang, Xinghua et al, Journal of Organic Chemistry, 2023, 88(13), 8268-8278

合成路线：3 步

反应条件：

1.1R:O2, C:Cu(OAc)2, S:ClCH2CH2Cl, 6 h, 80°C
2.1R:1-Benzotriazolol, R:EtN=C=N(CH2)3NMe2 •HCl, S:THF, overnight, 25°C
3.1R:Bu4N+ •HSO4-, C:Cu(OAc)2, S:MeCN, 6 h, 80°C

参考文献：

Copper-Catalyzed Transamidation of Unactivated Secondary Amides via C-H and C-N Bond Simultaneous Activations

By Lv, Cong et al, Journal of Organic Chemistry, 2023, 88(4), 2140-2157

合成路线：2 步

51583-97-2

110-91-8

1228377-92-1

反应条件：

1.1R:p-MeC6H4SO2N3, R:MeNH2, S:H2O, S:EtOH, 25 min, rt
2.1R:O2, C:CuI, S:MeCN, 10 min, 20-25°C, 1 atm
2.2S:MeCN, 3 h, 20-25°C

参考文献：

Copper-Catalyzed Oxidative Amidation for the Synthesis of α-Ketoamides from α-Diazoketones with Amines Using Oxygen as Oxidant

By Zhang, Jianlan et al, Asian Journal of Organic Chemistry, 2022, 11(8), e202200264

合成路线：3 步

反应条件：

1.1C:Cu(OAc)2, S:ClCH2CH2Cl, 6 h, rt
2.1R:1-Benzotriazolol, R:EtN=C=N(CH2)3NMe2 •HCl, S:THF, overnight, 25°C
3.1C:Cu(OAc)2, S:ClCH2CH2Cl, 6 h, rt

参考文献：

From amides to urea derivatives or carbamates with chemospecific C-C bond cleavage at room temperature

By Lv, Cong et al, Organic Chemistry Frontiers, 2022, 9(5), 1354-1363

合成路线：1 步

110-91-8

136415-67-3

_69%

1228377-92-1

反应条件：

1.1R:O2, C:Cu(OAc)2, S:DMF, 6 h, 80°C

参考文献：

Cu-Catalyzed aerobic oxidative cleavage of C(sp3)-C(sp3) bond: Synthesis of α-ketoamides

By Zhang, Jingming et al, Tetrahedron Letters, 2020, 61(47), 152555

合成路线：1 步

75681-34-4

110-91-8

_80%

1228377-92-1

反应条件：

1.1R:AcOH, R:H2O, C:Cu(OAc)2, S:MeCN, rt

参考文献：

Cu(OAc)2 and acids promoted oxidative cleavage of α-aminocarbonyl compounds with amines: efficient and selective synthesis of 2-t-amino-2-imino-carbonyl and 2-amino-2-oxocarbonyl compds.

By Chen, De et al, Tetrahedron Letters, 2020, 61(22), 151913

合成路线：1 步

反应条件：

1.1R:4-DMAP, R:O2, C:CuSC.tbd.N, S:PhMe, 10 h, 70°C

参考文献：

Chemoselective C(α)-C(β) bond cleavage of saturated aryl ketones with amines leading to α-ketoamides: a copper-catalyzed aerobic oxidation process with air

By Liu, Chengkou et al, Organic Chemistry Frontiers, 2017, 4(12), 2375-2379

合成路线：1 步

939-27-5

110-91-8

_71%

1228377-92-1

反应条件：

1.1R:t-BuOOH, R:H2O, C:I2, C:C5H5N, 10 h, 80°C
1.2R:t-BuOOH, R:NaI, R:H2O, 6 h, rt

参考文献：

One pot synthesis of α-ketoamides from ethylarenes and amines: a metal free difunctionalization strategy

By Ramanathan, Mani et al, Organic & Biomolecular Chemistry, 2016, 14(48), 11446-11453

合成路线：1 步

110-91-8

62550-65-6

_59%

1228377-92-1

反应条件：

1.1R:4-DMAP, R:O2, C:Cu2O, S:Xylene, 24 h, 140°C, 101 kPa

参考文献：

Copper-catalyzed oxidative amidation of aryl ketone and its derivatives to form α-keto amides

By Gong, Jiuhan et al, Youji Huaxue, 2015, 35(9), 1917-1922

合成路线：1 步

1485-07-0

110-91-8

_82%

1228377-92-1

反应条件：

1.1R:K2CO3, R:O2, C:CuBr, C:Me4-piperidoxyl, S:DMSO, 12 h, 70°C

参考文献：

Copper-TEMPO-catalyzed synthesis of α-ketoamides via tandem sp3C-H aerobic oxidation and amination of phenethyl alcohol derivatives

By Liu, Chengkou et al, Organic & Biomolecular Chemistry, 2016, 14(36), 8570-8575

合成路线：1 步

110-91-8

62244-84-2

_67%

1228377-92-1

反应条件：

1.1R:(PhCO2)2, R:O2, C:Cu(OAc)2, S:DMSO, 15 h, 110°C

参考文献：

Copper-Catalyzed C-N Bond Formation via Oxidative Cross-Coupling of Amines with α-Aminocarbonyl Compounds

By Liu, Xing-Xing et al, Advanced Synthesis & Catalysis, 2016, 358(15), 2385-2391

合成路线：1 步

7228-47-9

110-91-8

_98%

1228377-92-1

反应条件：

1.1R:H2O2, C:KI, C:H2SO4, S:DMF, S:H2O, 3 min, 60°C
1.2R:H2O2, S:DMF, S:H2O, 2 h, 60°C

参考文献：

A two-step continuous synthesis of α-ketoamides and α-amino ketones from 2° benzylic alcohols using hydrogen peroxide as an economic and benign oxidant

By Liu, Chengkou et al, RSC Advances, 2016, 6(30), 25167-25172

合成路线：1 步

93-08-3

110-91-8

_88%

1228377-92-1

反应条件：

1.1R:I2, R:O2, C:Dioxane, 16 h, 90°C; 90°C → rt
1.2R:Na2S2O3, S:H2O, rt

参考文献：

I2-promoted aerobic oxidative coupling of acetophenes with amines under metal-free conditions: facile access to α-ketoamides

By Guo, Shiyu et al, RSC Advances, 2016, 6(2), 1503-1507

合成路线：1 步

14289-45-3

110-91-8

_85%

1228377-92-1

反应条件：

1.1R:Cl(O=)CC(=O)Cl, C:DMF, S:CH2Cl2, > 1 h, rt; rt → 0°C
1.2R:Et3N, cooled; 1 h, rt
1.3R:H2O

参考文献：

Copper-Catalyzed Synthesis of Azaspirocyclohexadienones from α-Azido-N-arylamides under an Oxygen Atmosphere

By Chiba, Shunsuke et al, Journal of the American Chemical Society, 2010, 132(21), 7266-7267

791780-06-8(3-(3,4-二氯苯氧基)吖丁啶) 791778-53-5(trans-4-[2-[4-(2,3-Dichlorophenyl)piperazin-1-yl]ethyl]cyclohexanamine) 79201-37-9(4-N-叔丁氧羰基-4-N-甲基氨基哌啶) 787564-37-8((3R)-3-fluoropiperidine;hydrochloride) 78784-70-0(3-CHLORO-6-(2-PYRIDINYLMETHYL)PYRIDAZINE) 78789-65-8(butyl 3-(trichlorostannyl)propanoate compound with 2,2'-bipyridine (1:1) (en)) 792913-82-7((8-甲基-1,4-二氧杂螺[4.5]癸烷-8-基)氨基甲酸叔丁酯) 79324-78-0(1-(3-溴-4-(甲基硫代)苯基)乙酮)

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1228377-92-1 ((1,2-Ethanedione, 1-(4-morpholinyl)-2-(2-naphthalenyl)-)

1,2-Ethanedione, 1-(4-morpholinyl)-2-(2-naphthalenyl)-(1228377-92-1)名称与标识符

名称

标识符

1,2-Ethanedione, 1-(4-morpholinyl)-2-(2-naphthalenyl)-(1228377-92-1)合成路线

目录