3594-36-3|1,3-Di-p-tolylpropane-1,3-dione| Ambeed

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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1
[ 3594-36-3 ]
[ 6335-76-8 ]
[ 94104-37-7 ]

Reference： [1]Synthesis,1984,p. 663 - 664

2
[ 3594-36-3 ]
[ 105141-03-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium fluoride; 4-toluenesulfonyl azide
94%	With 4-acetamidobenzenesulfonyl azide; triethylamine In acetonitrile at 0 - 20℃;
87%	With potassium fluoride; dibenzo-18-crown-6; 4-toluenesulfonyl azide In dichloromethane for 5h; Ambient temperature;

Reference： [1]Korneev; Richter [Synthesis, 1995, # 10, p. 1248 - 1250]
[2]Chen, Xingpeng; Huang, Zhengshuo; Xu, Jiaxi [Advanced Synthesis and Catalysis, 2021, vol. 363, # 12, p. 3098 - 3108]
[3]Popic; Korneev; Nikolaev; Korobitsyna [Synthesis, 1991, # 3, p. 195 - 198]

3
[ 94-08-6 ]
[ 122-00-9 ]
[ 3594-36-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydroxide
80%	With sodium hydride In tetrahydrofuran; mineral oil at 0 - 40℃; for 17h; Inert atmosphere;
66%	With sodium hydride In benzene for 10h;

33%

With sodium hydride In tetrahydrofuran; mineral oil Inert atmosphere; Reflux;

Reference： [1]Ohta, Kazuchika; Muroki, Hiromitsu; Takagi, Akira; Yamamoto, Iwao; Matszaki, Kei [Molecular Crystals and Liquid Crystals (1969-1991), 1986, vol. 135, p. 247 - 264]
[2]Galán, Laura Abad; Reid, Brodie L.; Stagni, Stefano; Sobolev, Alexandre N.; Skelton, Brian W.; Cocchi, Massimo; Malicka, Joanna M.; Zysman-Colman, Eli; Moore, Evan G.; Ogden, Mark I.; Massi, Massimiliano [Inorganic Chemistry, 2017, vol. 56, # 15, p. 8975 - 8985]
[3]Choshi; horimoto; Wang; Nagase; Ichikawa; Sugino; Hibino [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 4, p. 1047 - 1049]
[4]Howard, Joseph L.; Sagatov, Yerbol; Repusseau, Laura; Schotten, Christiane; Browne, Duncan L. [Green Chemistry, 2017, vol. 19, # 12, p. 2798 - 2802]
[5]Yamada, Tohru; Nagata, Takushi; Sugi, Kiyoaki D.; Yorozu, Kiyotaka; Ikeno, Taketo; Ohtsuka, Yuhki; Miyazaki, Daichi; Mukaiyama, Teruaki [Chemistry - A European Journal, 2003, vol. 9, # 18, p. 4485 - 4509]

4
[ 99-75-2 ]
[ 122-00-9 ]
[ 3594-36-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 16h; Inert atmosphere; Reflux;
85%	With sodium hydride In dimethyl sulfoxide; mineral oil at 20 - 30℃; for 2h; Inert atmosphere; Sealed tube;
83.4%	With sodium hydride In tetrahydrofuran; dimethyl sulfoxide 1.) 3-5 to 20 deg C, 30 min, 2.) 30 deg C, 50 min;

64%	With sodium hydride In tetrahydrofuran; mineral oil at 20℃;
50%	With sodium hydride In tetrahydrofuran at 0℃; for 16h; Inert atmosphere; Reflux;	1,3-Bis(4-methylphenyl)propane-1,3-dione(37b). NaH (2.00 g, 50 mmol, 60% in oil) was washed free from oil with dryhexane (10 mL) at 0C under Ar. Dry THF (30 mL) was added, followed by methyl4-methylbenzoate (3.30 g, 22 mmol) in dry THF (10 mL) and 4-methyl-1-acetylbenzene (2.66 g, 20 mmol) in dry THF (10mL) at 0C under Ar. The suspension was stirred under reflux for 16 h. The mixturewas cooled and filtered (Celite). The solid was washed with EtOH(20 mL). The combined filtrates were poured into Et2O (20 mL) andaq. HCl (1 M, 20 mL). The aq. layer was extracted (Et2O, 2 ). The combinedextracts were washed (brine, 3 ) and dried. Evaporation and recrystallisation (EtOH) gave 37b(2.50 g, 50%) as yellow needles: mp 112-113C (lit.17 117-118C); 1HNMR (CDCl3) (enol) d 2.46 (6 H, s, 2 × Me), 6.84(1 H, s, CH), 7.31 (4 H, d, J = 8.0Hz, 2 × Ph 3,5-H2), 7.91 (4 H, d, J = 8.5 Hz, 2 × Ph 2,6-H2); 13C NMR (CDCl3)d 21.65 (2 × Me), 92.50(CH), 127.18 (2 × Ph 2,6-C2), 129.39 (2 × Ph 3,5-C2),132.94 (2 × Ph 1-C), 143.11 (2 × Ph 4-C), 185.50 (C=O, C-OH); MS m/z 527.2193 (2 M + Na)+ (C34H32NaO4requires 527.2188), 275.1055 (M + Na)+ (C17H16NaO2requires 275.1043).
17%	With sodium hydride In toluene Inert atmosphere; Reflux;
	With sodium methylate In methanol; 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 5h;	Synthesis of 1,3-diphenylpropane-1,3-dione (1a) General procedure: To the mixture of acetophenone (0.60 g, 5 mmol) and methyl benzoate (2.72 g,20 mmol) in 50 mL of xylene, sodium methoxide (0.43 g, 8 mmol) in 10 mL ofmethanol was added dropwise. Then the mixture was stirred at 120 oC, and themethanol was separated off continuously using a methanol knockout trap. After that,the mixture was further stirred for 5 h under refluxing condition. Then the reactionsystem was cooled to room temperature, 10 mL of water and 10 mL of 30% ofsulfuric acid were added. And the organic layer was separated out, washed with 2×10mL of 5% of sodium bicarbonate and 20 mL of water, dried by anhydrous sodiumsulfate, and evaporated under reduced pressure. The residue was subjected to thecolumn chromatography using ethyl acetate and petroleum ether (1:50) as eluent togive product in 62% yield. Other 1,3-diketones 1b-1n were prepared in similarmanner.
	Stage #1: para-methylacetophenone With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: 4-methyl-benzoic acid methyl ester In tetrahydrofuran at 0 - 20℃;
	With sodium hydride In tetrahydrofuran; mineral oil at 20℃;
	With sodium hydride In tetrahydrofuran; mineral oil Inert atmosphere; Reflux;
	Stage #1: para-methylacetophenone With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: 4-methyl-benzoic acid methyl ester In tetrahydrofuran at 25℃;
	With sodium hydride In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;
	With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Reflux;

Reference： [1]Martinez-Haya, Rebeca; Marzo, Leyre; König, Burkhard [Chemical Communications, 2018, vol. 54, # 82, p. 11602 - 11605]
[2]Zou, Liang-Hua; Priebbenow, Daniel L.; Wang, Long; Mottweiler, Jakob; Bolm, Carsten [Advanced Synthesis and Catalysis, 2013, vol. 355, # 13, p. 2558 - 2563]
[3]Franek [Monatshefte fur Chemie, 1996, vol. 127, # 8-9, p. 895 - 907]
[4]An, Zhenyu; Liu, Yafeng; Yan, Rulong; Zhao, Pengbo [Advanced Synthesis and Catalysis, 2021, vol. 363, # 13, p. 3240 - 3244]
[5]Kumpan, Katerina; Nathubhai, Amit; Zhang, Chenlu; Wood, Pauline J.; Lloyd, Matthew D.; Thompson, Andrew S.; Haikarainen, Teemu; Lehtiö, Lari; Threadgill, Michael D. [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3013 - 3032]
[6]Beck, Thorsten M.; Breit, Bernhard [Organic Letters, 2016, vol. 18, # 1, p. 124 - 127]
[7]Li, Zheng; Li, Tianpeng; Li, Jiasheng; He, Lili; Jia, Xianggui; Yang, Jingya [Synlett, 2015, vol. 26, # 20, p. 2863 - 2865]
[8]Qian, Jinlong; Yi, Wenbin; Huang, Xin; Jasinski, Jerry P.; Zhang, Wei [Advanced Synthesis and Catalysis, 2016, vol. 358, # 17, p. 2811 - 2816]
[9]Yoshidomi, Shohei; Abe, Manabu [Journal of the American Chemical Society, 2019, vol. 141, # 9, p. 3920 - 3933]
[10]He, Jian-Ping; Huang, Guo-Sheng; Luo, Nan; Zhan, Zhen-Zhen; Zhang, Ming-Ming [Organic and Biomolecular Chemistry, 2020, vol. 18, # 48, p. 9831 - 9835]
[11]Biswas, Rayhan G.; Ray, Sumit K.; Unhale, Rajshekhar A.; Singh, Vinod K. [Organic Letters, 2021, vol. 23, # 16, p. 6504 - 6509]
[12]Sadhu, Milon M.; Ray, Sumit K.; Unhale, Rajshekhar A.; Singh, Vinod K. [Organic and Biomolecular Chemistry, 2022, vol. 20, # 2, p. 410 - 414]
[13]Ning, Yongquan; Song, Qingmin; Sivaguru, Paramasivam; Wu, Lizuo; Anderson, Edward A.; Bi, Xihe [Organic Letters, 2022, vol. 24, # 2, p. 631 - 636]

5
[ 3594-36-3 ]
[ 240414-62-4 ]
[ 625096-39-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In methanol at 50℃; for 40h;
	With Tetrahydrofurfuryl alcohol; sodium tetrahydroborate; ethanol In chloroform at -20℃;

Reference： [1]Hu, Aiguo; Lin, Wenbin [Organic Letters, 2005, vol. 7, # 3, p. 455 - 458]
[2]Yamada, Tohru; Nagata, Takushi; Sugi, Kiyoaki D.; Yorozu, Kiyotaka; Ikeno, Taketo; Ohtsuka, Yuhki; Miyazaki, Daichi; Mukaiyama, Teruaki [Chemistry - A European Journal, 2003, vol. 9, # 18, p. 4485 - 4509]

6
[ 3594-36-3 ]
[ 27450-45-9 ]

Reference： [1]Yamada, Tohru; Nagata, Takushi; Sugi, Kiyoaki D.; Yorozu, Kiyotaka; Ikeno, Taketo; Ohtsuka, Yuhki; Miyazaki, Daichi; Mukaiyama, Teruaki [Chemistry - A European Journal, 2003, vol. 9, # 18, p. 4485 - 4509]

7
[ 3594-36-3 ]
[ 86396-75-0 ]
[ 625096-39-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In methanol at 50℃; for 5h;

Reference： [1]Hu, Aiguo; Lin, Wenbin [Organic Letters, 2005, vol. 7, # 3, p. 455 - 458]

9
[ 3594-36-3 ]
[ 17263-64-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With 4-toluenesulfonyl azide; methylamine In ethanol; water at 20℃; for 0.5h;
	Multi-step reaction with 2 steps 1: 96 percent / TsN₃, KF 2: 93 percent / Al₂O₃ / pentane; diethyl ether
	With 4-toluenesulfonyl azide; methylamine In ethanol; water at 23℃; Inert atmosphere;

With 4-acetamidobenzenesulfonyl azide; benzylamine In ethanol at 20℃;

Reference： [1]Zhang, Jianlan; Chen, Wenwen; Huang, Dayun; Zeng, Xiaobao; Wang, Xinyan; Hu, Yuefei [Journal of Organic Chemistry, 2017, vol. 82, # 17, p. 9171 - 9174]
[2]Korneev; Richter [Synthesis, 1995, # 10, p. 1248 - 1250]
[3]Suneja, Arun; Schneider, Christoph [Organic Letters, 2018, vol. 20, # 23, p. 7576 - 7580]
[4]Dong, Yirong; Tian, Yu; Zhang, Zunting; Wang, Tao [Advanced Synthesis and Catalysis, 2022, vol. 364, # 23, p. 4026 - 4030]

10
[ 5153-67-3 ]
[ 3594-36-3 ]
[ 1134100-06-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With (R)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanamine In diethyl ether at 23℃; for 24h; optical yield given as %ee; enantioselective reaction;
85%	In diethyl ether at 23℃; for 24h;	1 2-((S)-2-Nitro-1-phenylethyl)-1,3-dip-tolylpropane-1,3-dione (3p) 2-((S)-2-Nitro-1-phenylethyl)-1,3-dip-tolylpropane-1,3-dione (3p) To a solution of dione 1b (0.1 mmol, 1 eq) and trans-β-nitrostyrene 2a (0.2 mmol, 2 eq) in diethyl ether (0.2 mL) was added catalyst VI (Q-NH2) (0.015 mmol, 0.15 eq). The resulting mixture was stirred at room temperature (23° C.) for 24 hours. The product was purified by flash chromatography over silica gel (EtOAc:Hexane=1:10 to 1:5) to provide the title compound (85% yield). 1H-NMR (400 MHz, CDCl3) δ 7.80 (d, J=8.0 Hz, 2H), 7.73 (d, J=8.0 Hz, 2H), 7.28-7.16 (m, 9H), 5.80 (d, J=8.0 Hz, 1H), 5.01 (d, J=6.8 Hz, 2H), 4.64 (dd, J=7.6, 14.4 Hz, 1H), 2.39 (s. 3H), 2.37 (s, 3H). 13C-NMR (100 MHz, CDCl3) δ 193.8, 193.1, 145.2, 144.9, 137.0, 133.8, 133.3, 129.7, 129.5, 128.96, 128.93, 128.8, 128.3, 128.1, 59.7, 44.1, 21.7, 21.7.

Reference： [1]Tan, Bin; Zhang, Xuan; Chua, Pei Juan; Zhong, Guofu [Chemical Communications, 2009, # 7, p. 779 - 781]
[2]Current Patent Assignee: NANYANG TECHNOLOGICAL UNIVERSITY - US2012/4424, 2012, A1 Location in patent: Page/Page column 12

11
[ 3594-36-3 ]
[ 3457-48-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With iodine; dimethyl sulfoxide; copper(ll) bromide for 8h; Schlenk technique; Heating;
80%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; acetic acid; copper(I) bromide at 100℃; for 2h;
60%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(I) triflate In N,N-dimethyl-formamide at 120℃;	7 Example 7: Synthesis of 1,2-bis(4-methylphenyl)ethanedione 1,3-bis(4-methylphenyl)propane-1,3-dione as a starting material, the reaction procedure is as follows: Reaction flask was added 1,3-bis(4-methylphenyl)propane-1,3-dione (0.25g, 1mmol), 2,2,6,6-tetramethylpiperidine-N-oxide (0.16g, 1mmol), cuprous trifluoromethanesulfonate (0.021g, 0.1mmol) and dimethylformamide (2 ml), 120°C reaction; TLC until the reaction was followed completely finished; After completion of the reaction the crude product obtained was purified by column chromatography (petroleum ether: ethyl acetate = 40), To give the desired product (60% yield)

49%	With pyridine; oxygen; copper(I) bromide In toluene at 100℃; for 24h;	2): 1,2-Bis-p-tolylethane-1,2-dione. 2): 1,2-Bi-p-tolylethane-1,2-dione.2 The reaction of CuBr (3.6 mg, 0.025 mmol), pyridine (10.0 mg, 0.125 mmol), 1,3-di-p-tolylpropane-1,3-dione 1b (63.1 mg, 0.25 mmol) in toluene (2 mL), at 100 °C, under O2 (1 atm), for 24 h, afforded 29 mg (49%) of 2b. 2b: yellow solid; 1H NMR (CDCl3, 400 MHz): δ = 7.86 (d, J= 8.4 Hz, 4H), 7.30 (d, J= 8.0 Hz, 4H), 2.43 (s, 6H); 13C NMR (CDCl3, 100 MHz): δ = 194.5, 146.1, 130.7, 130.0, 129.7, 21.9 ppm; IR (neat): ν = 3451.2, 2919.0, 1662.7, 1172.5 cm-1; MW (EI): 238.4.
84 %Chromat.	With iodine; dimethyl sulfoxide at 150℃; for 27h;

Reference： [1]Chen, Li-Sha; Zhang, Lu-Bing; Tian, Yue; Li, Jin-Heng; Liu, Yong-Quan [European Journal of Organic Chemistry, 2020, vol. 2020, # 34, p. 5523 - 5526]
[2]Zhou, Peng-Jun; Li, Cheng-Kun; Zhou, Shao-Fang; Shoberu, Adedamola; Zou, Jian-Ping [Organic and Biomolecular Chemistry, 2017, vol. 15, # 12, p. 2629 - 2637]
[3]Current Patent Assignee: CHINASUN SPECIALTY PRODUCTS - CN105348060, 2016, A Location in patent: Paragraph 0023
[4]Zhang, Chun; Wang, Xiaoyang; Jiao, Ning [Synlett, 2014, vol. 25, # 10, p. 1458 - 1460]
[5]Location in patent: experimental part Yuan, Yu; Zhu, Haitao [European Journal of Organic Chemistry, 2012, # 2, p. 329 - 333]

12
[ 3594-36-3 ]
[ 832737-81-2 ]

Yield	Reaction Conditions	Operation in experiment
32%	With ruthenium trichloride; potassium peroxymonosulfate; ammonium chloride In water; ethyl acetate; acetonitrile at 20℃;

Reference： [1]Location in patent: experimental part Allpress, Caleb J.; Arif, Atta M.; Houghton, Dylan T.; Berreau, Lisa M. [Chemistry - A European Journal, 2011, vol. 17, # 52, p. 14962 - 14973]

13
[ 67-56-1 ]
[ 3594-36-3 ]
[ 21947-71-7 ]
[ 1449389-00-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 1,3-bis(p-methylphenyl)-1,3-propanedione; cinnamic anhydride With (2S,3R)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine In dichloromethane at 0 - 20℃; Stage #2: methanol enantioselective reaction;

Reference： [1]Robinson, Emily R. T.; Fallan, Charlene; Simal, Carmen; Slawin, Alexandra M. Z.; Smith, Andrew D. [Chemical Science, 2013, vol. 4, # 5, p. 2193 - 2200]

14
[ 110-18-9 ]
[ 3594-36-3 ]
[ 170647-13-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	With dipotassium peroxodisulfate In acetonitrile at 60℃; for 5h; Sealed tube;	General procedure for the methylene-bridged bis-1,3-dicarbonyl compounds 3a-t General procedure: K2S2O8 (270mg, 1.0mmol), dibenzoylmethane 1a (112mg, 0.5mmol) were added to a solution of N,N,N′,N′-tetramethylethylenediamine 2a (116mg, 1.0mmol) in CH3CN (2.0mL), the reaction mixture was stirred in a sealed tube at 60°C for 5h. The reaction was monitored by TLC. Once the reaction was completed, the reaction mixture was treated with H2O (5.0mL) and EtOAc (8.0mL). The organic and aqueous layers were then separated, and the aqueous layer was extracted with EtOAc (3×8mL). The combined organic extracts were dried (Na2SO4), then the solvent was removed under reduced pressure and the remaining residue was purified by column chromatography. Compound 3a (110.4mg, 96% yield) was obtained as a light yellow powder.

Reference： [1]Wang, Xiaohu; Wang, Yi; Yuan, Yu; Xing, Chun-Hui [Tetrahedron, 2014, vol. 70, # 12, p. 2195 - 2202]

15
[ 3594-36-3 ]
[ 75326-15-7 ]
[ 1644277-66-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In dichloromethane; water at 20℃; for 8h;
	With potassium carbonate In dichloromethane; water at 20℃; for 8h;
	With potassium carbonate In dichloromethane; water at 20℃; for 8h; Inert atmosphere; Schlenk technique;

With potassium carbonate In dichloromethane; water at 20℃; for 8h;

Reference： [1]Xia, Yong; Liu, Xiaohua; Zheng, Haifeng; Lin, Lili; Feng, Xiaoming [Angewandte Chemie - International Edition, 2015, vol. 54, # 1, p. 227 - 230][Angew. Chem., 2015, # 1, p. 4][Angewandte Chemie, 2015, # 1, p. 4]
[2]Xia, Yong; Lin, Lili; Chang, Fenzhen; Fu, Xuan; Liu, Xiaohua; Feng, Xiaoming [Angewandte Chemie - International Edition, 2015, vol. 54, # 46, p. 13748 - 13752]
[3]Zhang, Jingfang; Tang, Yuhai; Wei, Wen; Wu, Yong; Li, Yang; Zhang, Junjie; Zheng, Yuansuo; Xu, Silong [Organic Letters, 2017, vol. 19, # 12, p. 3043 - 3046]
[4]Wei, Wen; Tang, Yuhai; Zhou, Yan; Deng, Ge; Liu, Ziyu; Wu, Jun; Li, Yang; Zhang, Junjie; Xu, Silong [Organic Letters, 2018, vol. 20, # 20, p. 6559 - 6563]

16
[ 3594-36-3 ]
[ 1075-06-5 ]
[ 1691212-92-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium carbonate; toluene-4-sulfonic acid hydrazide In water; N,N-dimethyl-formamide at 100℃; for 2h; regioselective reaction;

Reference： [1]Shu, Wen-Ming; Zheng, Kai-Lu; Ma, Jun-Rui; Sun, Hui-Ying; Wang, Mei; Wu, An-Xin [Organic Letters, 2015, vol. 17, # 8, p. 1914 - 1917]

17
[ 35905-85-2 ]
[ 3594-36-3 ]
[ 1793105-56-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With caesium carbonate In acetonitrile for 10h; Reflux;	4.1.55. 7-(4-Methylphenyl)pyrano[4,3-b]pyridin-5-one (26b) Compound 38 (101.5 mg, 0.5 mmol) was boiled under refluxwith 37b (252 mg, 1.0 mmol) and Cs2CO3 (163 mg, 0.5 mmol) inMeCN (15 mL) for 10 h. The mixture was cooled and poured intowater (10 mL) and the mixture was extracted with CH2Cl2 (3).The combined extracts were dried. The evaporation residue wassuspended in petroleum ether (50 mL). The mixture was sonicatedand was filtered. The collected solid was washed (water, petroleumether) to give 26b (110 mg, 93%) as an off-white powder: mp 135-136 C; 1H NMR (CDCl3) d 2.41 (3H, s, Me), 7.16 (1H, s, 8-H), 7.28(2H, d, J = 8.0 Hz, Ph 3,5-H2), 7.38 (1H, dd, J = 7.9, 4.7 Hz, 3-H),7.80 (2H, d, J = 8.3 Hz, Ph 2,6-H2), 8.52 (1H, ddd, J = 7.9, 1.7,0.6 Hz 4-H), 8.92 (1H, dd, J = 4.7, 1.8 Hz, 2-H); 13C NMR (CDCl3) d21.0 (Me), 102.92 (8-C), 117.0 (4a-C), 123.0 (3-C), 125.55 (Ph 2,6-C2), 126.0 (Ph 1-C), 129.68 (Ph 3,5-C2), 137.52 (4-C), 141.0 (4-C),150.0 (7-C), 156.33 (5-C), 158.0 (2-C), 162.0 (8a-C); MS m/z238.0850 (M+Na)+ (C15H12NNaO2 requires 238.0863).

Reference： [1]Kumpan, Katerina; Nathubhai, Amit; Zhang, Chenlu; Wood, Pauline J.; Lloyd, Matthew D.; Thompson, Andrew S.; Haikarainen, Teemu; Lehtiö, Lari; Threadgill, Michael D. [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3013 - 3032]

18
[ 3594-36-3 ]
[ 15366-62-8 ]
3-(4-methylphenyl)pyrano[3,4-c]pyridin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With caesium carbonate; In acetonitrile; for 48h;Reflux;	Compound 39 (101.5 mg, 0.5 mmol) was heated under refluxwith 37b (252 mg, 1.0 mmol) and Cs2CO3 (163 mg, 0.5 mmol) inMeCN (15 mL) for 2 d. The mixture was cooled, poured into waterand extracted thrice with CH2Cl2. The combined extracts weredried. The evaporation residue was suspended in petroleum ether(50 mL) and sonicated. The solid was collected and washed (water,petroleum ether) to give 40b (38 mg, 32%) as an off-white powder:mp 120-123 C; 1H NMR (CDCl3) d 2.45 (3H, s, Me), 6.90 (1H, s, 4-H), 7.31 (2H, d, J = 8.0 Hz, Ph 3,5-H2), 7.33 (1H, d, J = 5.5 Hz, 5-H),7.83 (2H, d, J = 8.0 Hz, Ph 2,6-H2), 8.83 (1H, d, J = 5.5 Hz, 6-H),9.49 (1H, s, 8-H); 13C NMR (CDCl3) d 20.5 (Me), 100.0 (4-C), 118.0(4a-C), 118.5 (5-C), 121.5 (Ph 1-C), 125.80 (Ph 2,6-C2), 128.9 (Ph4-C), 129.79 (Ph 3,5-C2), 130.0 (3-C), 139.5 (8-C), 141.0 (8a-C),154.0 (6-C), 159.5 (1-C); MS m/z 238.0851 (M+H)+ (C15H12NO2requires 238.0863).

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3013 - 3032

19
[ 3594-36-3 ]
[ 15366-62-8 ]
3-(4-methylphenyl)-2,7-naphthyridin-1-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3013 - 3032

20
[ 3594-36-3 ]
[ 873396-38-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium fluoride; water; sodium hydroxide In N,N-dimethyl-formamide at 120℃; for 12h; Green chemistry;	The general procedure for 2-hydroxylation of 1,3-diketones General procedure: The mixture of 1,3-diketone (1.0 mmol), potassium fluoride (0.1 mmol), sodium hydroxide (0.2 mmol) in 4.8 mL of DMF and 0.2 mL of H2O was stirred at 120 oCunder air for 12 h. After the completion of the reaction monitored by TLC, the mixture was cooled to room temperature, diluted with ethyl acetate and washed withsaturated sodium carbonate solution. The resulting organic phase was dried overanhydrous magnesium sulfate, and concentrated under reduced pressure. The residuewas isolated by column chromatography using petroleum ether and ethyl acetate (20 :1) as eluent to give pure product. The analytical data for products are given below.

Reference： [1]Li, Zheng; Li, Tianpeng; Li, Jiasheng; He, Lili; Jia, Xianggui; Yang, Jingya [Synlett, 2015, vol. 26, # 20, p. 2863 - 2865]

21
[ 3594-36-3 ]
[ 100-58-3 ]
[ 1831158-21-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 1,3-bis(p-methylphenyl)-1,3-propanedione With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: phenylmagnesium bromide In tetrahydrofuran at 40℃; for 4h; Inert atmosphere; regioselective reaction;

Reference： [1]Yuan, Rui; Zhao, Dan; Zhang, Li-Yuan; Pan, Xiang; Yang, Yan; Wang, Pei; Li, Hong-Feng; Da, Chao-Shan [Organic and Biomolecular Chemistry, 2015, vol. 14, # 2, p. 724 - 728]

22
[ 614-45-9 ]
[ 3594-36-3 ]
[ 27450-45-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With copper(l) chloride In methanol at 80℃;	8 Example 8: Preparation of 1,3-bis(4-methylphenyl)-2-methylpropan-1,3-dione In order to 1,3-bis(4-methylphenyl)-propan-1,3-dione, tert-butyl peroxybenzoate is used as a raw material, the reaction steps are as follows:Added in the reaction bottle 1,3-bis(4-methylphenyl)-propan-1,3-dione (0.25g, 1mmol), tert-butyl peroxybenzoate (0.58g, 3mmol), CuCl (0.01g, 0 . 1mmol) and 2 ml methanol, 80 °C reaction;TLC until the complete end tracking of the reaction;After the reaction the crude product by column chromatography (petroleum ether: ethyl acetate = 40:1), to obtain the target product (yield 84%).
74%	With copper(l) chloride In acetic acid at 120℃; for 0.5h; chemoselective reaction;	3.5 4.2. General procedure for the methylation of 1,3-diketones (1 and 3) General procedure: To a solution of acetic acid (10 mL) containing 1,3-diphenylpropane-1,3-dione (1a) (0.224 g, 1.0 mmol) and CuCl (0.010 g, 0.1 mmol) was added tert-butyl peroxybenzoate (0.56 mL, 3.0 mmol), then the mixture was heated at 120 °C for 0.5 h, after completion of reaction (monitored by TLC), the solvent was removed under vacuum and the residue was neutralized by aqueous NaHCO3 solution and extracted with DCM (10 mL * 3). The combined organic fractions were dried over anhydrous MgSO4, and concentrated under vacuum to obtain the crude product, which was purified by column chromatography (silica gel, petroleum ether/EtOAc (95:5)) to give pure 2-methyl-1,3-diphenylpropane-1,3-dione (2a).

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN105254483, 2016, A Location in patent: Paragraph 0028
[2]Zhou, Zhi-Hao; Li, Cheng-Kun; Zhou, Shao-Fang; Shoberu, Adedamola; Zou, Jian-Ping [Tetrahedron, 2017, vol. 73, # 19, p. 2740 - 2746]

23
[ 3594-36-3 ]
[ 68-12-2 ]
[ 1912516-21-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With tert.-butylhydroperoxide; copper(l) iodide at 140℃;	5 Example 5: synthesis of 2-N, N- dimethyl-carbamoyl-1,3-di (4-methylphenyl) propan-1,3-dione 1,3-bis (4-methylphenyl) propan-1,3-dione, N, N- dimethylformamide as the raw material, the reaction procedure was as follows: In a reaction flask was added 1,3-bis (4-methylphenyl) propan-1,3-dione (0.252g, 1mmol), N, N- dimethylformamide (2 ml), cuprous iodide (0.019g, 0.1mmol) and t butylhydroperoxide (0.180g, 2mmol), at 140 deg C reaction; TLC until complete reaction was followed over; after the reaction, the crude product obtained was purified by column chromatography (petroleum ether: ethyl acetate = 4: 1) to give the target product(88% yield)
88%	With di-tert-butyl peroxide; copper(II) bis(trifluoromethanesulfonate) In N,N-dimethyl-formamide for 0.5h; Reflux;	4.3.5. N,N-Dimethyl-2-(4-methylbenzoyl)-3-oxo-3-(p-tolyl)propan-amide (3e) General procedure: Yellow oil (284 mg, 88% yield). 1H NMR (400 MHz, CDCl3): d 7.89(d, J 8.2 Hz, 2H), 7.62 (d, J 8.3 Hz, 2H), 7.29e7.23 (m, 4H), 7.15 (s,1H), 3.14 (s, 3H), 3.04 (s, 3H), 2.43 (s, 3H), 2.42 (s, 3H); 13C NMR(101 MHz, CDCl3): d 188.7, 157.9, 153.4, 143.2, 141.3, 136.6, 132.2,129.5, 129.2, 128.3, 126.3, 108.9, 36.8, 21.6, 21.5; HRMS (CI-TOF) m/z:M Calcd for C20H21NO3 323.1521, found 323.1543.

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN105503635, 2016, A Location in patent: Paragraph 0017
[2]Yan, Xu-Ping; Li, Cheng-Kun; Zhou, Shao-Fang; Shoberu, Adedamola; Zou, Jian-Ping [Tetrahedron, 2020, vol. 76, # 30]

24
[ 3594-36-3 ]
[ 121-45-9 ]
[ 1911593-46-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tert.-butylhydroperoxide; acetic acid; copper(l) chloride at 70℃;	3 Example 3: synthesis of 2-dimethylphosphonate-1,3-bis(4-methylphenyl)propan-1,3-dione In the reaction flask by adding 1,3-bis (4-methyl phenyl) - 1,3-propanedione (0.252g, 1 . 0mmol), trimethyl phosphite (0.372g, 3 . 0mmol), copper chloride (0.013g, 0 . 1mmol), T-butyl hydrogen peroxide (0.27g, 3mmol) and acetic acid (5 ml), 70 °C reaction;TLC until the complete end tracking of the reaction;After the reaction the crude product by column chromatography (petroleum ether: ethyl acetate = 4:1), to obtain the target product (yield 90%).
78%	With dilauryl peroxide; copper(I) bromide In acetic acid at 110℃; for 0.5h;

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN105503945, 2016, A Location in patent: Paragraph 0018
[2]Li, Cheng-Kun; Tao, Ze-Kun; Zhou, Zhi-Hao; Bao, Xiao-Guang; Zhou, Shao-Fang; Zou, Jian-Ping [Journal of Organic Chemistry, 2019, vol. 84, # 4, p. 2351 - 2357]

25
[ 3594-36-3 ]
[ 106-93-4 ]
[ 2098221-00-0 ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium carbonate In dimethyl sulfoxide at 20℃; for 34h; Inert atmosphere; Schlenk technique;
	With potassium carbonate In dimethyl sulfoxide at 20℃;

Reference： [1]Zhang, Jingfang; Tang, Yuhai; Wei, Wen; Wu, Yong; Li, Yang; Zhang, Junjie; Zheng, Yuansuo; Xu, Silong [Organic Letters, 2017, vol. 19, # 12, p. 3043 - 3046]
[2]Wei, Wen; Tang, Yuhai; Zhou, Yan; Deng, Ge; Liu, Ziyu; Wu, Jun; Li, Yang; Zhang, Junjie; Xu, Silong [Organic Letters, 2018, vol. 20, # 20, p. 6559 - 6563]

26
[ 1032818-12-4 ]
[ 3594-36-3 ]
[ 2098221-03-3 ]

Yield	Reaction Conditions	Operation in experiment
46%	With potassium carbonate In dichloromethane; water at 20℃; Inert atmosphere; Schlenk technique;
	With potassium carbonate In dichloromethane; water at 20℃; for 8h;

Reference： [1]Zhang, Jingfang; Tang, Yuhai; Wei, Wen; Wu, Yong; Li, Yang; Zhang, Junjie; Zheng, Yuansuo; Xu, Silong [Organic Letters, 2017, vol. 19, # 12, p. 3043 - 3046]
[2]Wei, Wen; Tang, Yuhai; Zhou, Yan; Deng, Ge; Liu, Ziyu; Wu, Jun; Li, Yang; Zhang, Junjie; Xu, Silong [Organic Letters, 2018, vol. 20, # 20, p. 6559 - 6563]

27
[ 3594-36-3 ]
[ 2136380-82-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 4-toluenesulfonyl azide; sodium carbonate; methylamine In water; N,N-dimethyl-formamide at 85℃; for 3h;	A typical procedure for preparation of 3,5-dibenzoyl-4-phenylpyrazole (4a) General procedure: To a stirred solution of 1,3-diphenylpropane-1,3-dione (1a, 269 mg, 1.2 mmol) and Na2CO3 (10.6 mg, 0.1 mmol) in DMF (2 mL) was added tosyl azide (98.6 mg, 0.5 mmol) and MeNH2 (40% aqueous solution, 46.6 mg, 0.6 mmol) successively. After the mixture was stirred at 85 C (oil bath) for 3 h (monitored by TLC), it was quenched with water. The resultant mixture was extracted with CH2Cl2 and the combined layers were dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the residue was purified by a flash chromatography [silica gel, 15% EtOAc in petroleum ether (60-90 C)] to give 164 mg (93%) of product 4a as a white solid.

Reference： [1]Zhang, Jianlan; Chen, Wenwen; Huang, Dayun; Zeng, Xiaobao; Wang, Xinyan; Hu, Yuefei [Tetrahedron Letters, 2017, vol. 58, # 43, p. 4133 - 4136]

28
[ 3594-36-3 ]
[ 67-64-1 ]
[ 2209100-45-6 ]

Yield	Reaction Conditions	Operation in experiment
73%	With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water at 50℃; for 2h; Schlenk technique; Green chemistry;	II. General procedure for the preparation of 3 and 5. 3a as an example General procedure: To a solution of the 1,3-diphenylpropane-1,3-dione 1a (67.2 mg, 0.3 mmol) in acetone (3.0 ml) was added TBHP (82 μL, 0.6 mmol, 70% in water) and nBu4NI (22.2 mg, 0.06 mmol) in a 25 mL Schlenk tube. The reaction was stirred for the 2.0 h at 50 C. After the reaction finished, the reaction mixture was cooled to room temperature and quenched by the addition of a saturated solution of Na2S2O3 (3.0 mL). The mixture was extracted with EtOAc (3 × 5.0 mL), the combined organic phases were dried over anhydrous Na2SO4 and the solvent was evaporated under vacuum. The residue was purified by column chromatography to give the corresponding products 3a (62.8 mg, 75%).

Reference： [1]Lv, Yunhe; Pu, Weiya; Niu, Jiejie; Wang, Qingqing; Chen, Qian [Tetrahedron Letters, 2018, vol. 59, # 15, p. 1497 - 1500]

29
[ 3594-36-3 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
80%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 4h; chemoselective reaction;

Reference： [1]Lad, Bapurao Sudam; Katukojvala, Sreenivas [ACS Catalysis, 2018, vol. 8, # 12, p. 11807 - 11814]

30
[ 3594-36-3 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
74%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 4h; chemoselective reaction;

Reference： [1]Lad, Bapurao Sudam; Katukojvala, Sreenivas [ACS Catalysis, 2018, vol. 8, # 12, p. 11807 - 11814]

31
[ 3594-36-3 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
68%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 4h; chemoselective reaction;

Reference： [1]Lad, Bapurao Sudam; Katukojvala, Sreenivas [ACS Catalysis, 2018, vol. 8, # 12, p. 11807 - 11814]

32
[ 3594-36-3 ]
[ 28383-65-5 ]
[ 1429514-89-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 12h; chemoselective reaction;

Reference： [1]Lad, Bapurao Sudam; Katukojvala, Sreenivas [ACS Catalysis, 2018, vol. 8, # 12, p. 11807 - 11814]

33
[ 3594-36-3 ]
[ 2361209-09-6 ]
[ 2361208-80-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With scandium tris(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 4.5h; Inert atmosphere;	6. General procedure D for C-H bond functionalization of 1,3-diketones General procedure: A mixture of Sc(OTf)3 (12.3 mg, 5 mol%) and 1,3-diphenylpropane-1,3-dione 2a (0.168 g, 0.75 mmol) was stirred in 2 mL DCE at room temperature in 25 mL two necked RB flask under inert atmosphere for 5 minutes. Then propargyl α-(4-methoxyphenyl)-α-diazoacetate 1a (0.115 g, 0.5 mmol) in 1 mL of DCE was added to the reaction mixture dropwise over 30 minutes and then the reaction mixture was stirred at room temperature* over 4h. The progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was removed under reduced pressure. The crude product obtained was purified by column chromatography over silica gel to furnish the desired product 3aa (0.205 g, 96% yield). The slightly excess 1,3-diketone 2a was recovered during the purification. (* - For the synthesis of compound 3ad and 3ae reaction mixture was stirred at 50 °C and ≠ - for the synthesis of compounds 3ha, 3hc and 3ia the reaction mixture was heated at 70 °C in presence of 10 mol% Sc(OTf)3.