[ CAS No. 120-46-7 ] {[proInfo.proName]}

Name: 120-46-7|1,3-Diphenylpropane-1,3-dione|98%
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Quality Control of [ 120-46-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 120-46-7 ]

Product Details of [ 120-46-7 ]

CAS No. :	120-46-7	MDL No. :	MFCD00003085
Formula :	C₁₅H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NZZIMKJIVMHWJC-UHFFFAOYSA-N
M.W :	224.25	Pubchem ID :	8433
Synonyms :		Chemical Name :	1,3-Diphenylpropane-1,3-dione

Calculated chemistry of [ 120-46-7 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.07
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	66.35
TPSA :	34.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.94
Log Po/w (XLOGP3) :	3.03
Log Po/w (WLOGP) :	3.14
Log Po/w (MLOGP) :	2.51
Log Po/w (SILICOS-IT) :	3.65
Consensus Log Po/w :	2.86

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.4
Solubility :	0.0898 mg/ml ; 0.0004 mol/l
Class :	Soluble
Log S (Ali) :	-3.41
Solubility :	0.0868 mg/ml ; 0.000387 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.22
Solubility :	0.00134 mg/ml ; 0.00000597 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.27

Safety of [ 120-46-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 120-46-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 120-46-7 ]
Downstream synthetic route of [ 120-46-7 ]

[ 120-46-7 ] Synthesis Path-Upstream 1~4

1
[ 855175-05-2 ]
[ 2678-54-8 ]
[ 120-46-7 ]

Reference： [1] Journal of the American Chemical Society, 1940, vol. 62, p. 1285

2
[ 120-46-7 ]
[ 2915-16-4 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 153 - 158
[2] Synthetic Communications, 1991, vol. 21, # 7, p. 901 - 906

3
[ 120-46-7 ]
[ 1576-35-8 ]
[ 14062-05-6 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1980, vol. 322, # 5, p. 816 - 820

4
[ 120-46-7 ]
[ 1576-35-8 ]
[ 14062-05-6 ]
[ 123909-09-1 ]
[ 1575-27-5 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1980, vol. 322, # 5, p. 816 - 820

[ 120-46-7 ] Synthesis Path-Downstream 1~88

1
[ 1004-38-2 ]
[ 120-46-7 ]
[ 20732-44-9 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 3449,3454

2
[ 593-85-1 ]
[ 120-46-7 ]
[ 40230-24-8 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 99

3
[ 2051-79-8 ]
[ 120-46-7 ]
[ 4754-96-5 ]

Reference： [1]Journal of the American Chemical Society,1957,vol. 79,p. 2919,2925
[2]Journal of the American Chemical Society,1957,vol. 79,p. 2919,2925

4
[ 120-46-7 ]
[ 95-54-5 ]
[ 716-79-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With gadolinium(III) chloride hexahydrate; at 80℃; for 5.5h;	General procedure: To a mixture of o-aromatic diamines (200 mg, 1.85 mmol) and 1,3-dicarbonyl compound (722 mg, 5.55 mmol), GdCl3*6H2O (25 mg, 0.09 mmol) was added and the mixture was stirred at 80°C for 3.0 hr. After completion of the reaction (TLC), the reaction mixture was poured into ice cold water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the corresponding 2-methyl benzimidazole. The crude material was further purified by through column chromatography by using 10percent ethyl acetate in hexane.
60%	With sodium iodide dichloride; In tetrahydrofuran; water; for 10h;Reflux; Sealed tube;	General procedure: To a mixture of o-substituted (?NH2 or ?SH or ?OH) anilines(1.0 mmol) and appropriate 1,3-diketones (1.1 mmol) in THF(5 mL) was added 30percentw/w aqueous NaICl2 (0.2 mmol, 20molpercent). The reaction was allowed to remain stirred at refluxtemperature for 2?3 h. After the reaction was complete, asindicated by TLC, the mixture was cooled to room temperature.The volatiles were removed under reduced pressureand treated successively with aqueous sodium thiosulphatesolution and saturated solution of NaHCO3, and extractedby ethylacetate (2×10 mL). The combined organic phaseswere washed with brine and dried over Na2SO4 and evaporatedunder vacuum. The crude reaction mixture was purifiedby column chromatography on silica gel using petroleumether/ethyl acetate as eluents.
45%	With benzoic acid; In ethanol; at 70℃; for 36h;Schlenk technique;	O-phenylenediamine (54.0 mg, 0.5 mmol), 1, 3-diphenyl-1,3-diacetone (134. 5 mg, 0. 6 mmol) and benzoic acid (6.1 mg, 0. 05 mmol) were added sequentially to a 25 mL Schlenk flask, In ethanol (6.OmL), placed in oil bath at 70 ° C for 36h. After completion of the reaction, the solvent was removed under reduced pressure, and petroleum ether / B was used Ethyl acetate as eluant. The yield of 2-phenylbenzimidazole was 45percent.

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2015,vol. 54B,p. 953 - 957
[2]Journal of Chemical Sciences,2018,vol. 130
[3]Organic Letters,2014,vol. 16,p. 764 - 767
[4]Patent: CN103910682,2016,B .Location in patent: Paragraph 0041-0043
[5]Gazzetta Chimica Italiana,1913,vol. 43 I,p. 302
[6]Synthetic Communications,2009,vol. 39,p. 175 - 188

5
[ 120-46-7 ]
[ 56-09-7 ]
[ 76-05-1 ]
2-amino-4-oxo-5,7-diphenyl-3,4-dihydro-pyrano[2,3-d]pyrimidinylium; trifluoroacetate [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1977,vol. 13,p. 1185 - 1187
Khimiya Geterotsiklicheskikh Soedinenii,1977,vol. 13,p. 1484 - 1486

6
[ 120-46-7 ]
[ 1979-98-2 ]
2-methylsulfanyl-5,7-diphenyl-pyrano[2,3-d]pyrimidin-4-one; perchlorate [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1977,vol. 13,p. 1185 - 1187
Khimiya Geterotsiklicheskikh Soedinenii,1977,vol. 13,p. 1484 - 1486

7
[ 120-46-7 ]
[ 17220-38-1 ]
[ 26261-74-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1970,vol. 7,p. 131 - 133

8
[ 28491-52-3 ]
[ 120-46-7 ]
3-oxo-4,6-diphenyl-2,3-dihydropyrazolo<3,4-b>pyridine [ No CAS ]
3-oxo-5,7-diphenyl-1,2-dihydropyrazolo<1,5-a>pyrimidine [ No CAS ]

Reference： [1]Polish Journal of Chemistry,1983,vol. 57,p. 1251 - 1261

9
[ 6855-64-7 ]
[ 120-46-7 ]
1,3-diphenyl-3-(2-phenyl-5-indolylamino)-2-propen-1-one [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 1299 - 1303
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 1520 - 1524

10
[ 6335-76-8 ]
[ 120-46-7 ]
[ 94104-34-4 ]

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

11
[ 120-46-7 ]
[ 1576-35-8 ]
[ 14062-05-6 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1980,vol. 322,p. 816 - 820

12
[ 120-46-7 ]
[ 1576-35-8 ]
[ 14062-05-6 ]
[ 123909-09-1 ]
[ 1575-27-5 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1980,vol. 322,p. 816 - 820

13
[ 120-46-7 ]
[ 1145-01-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With carbazic acid; at 90℃; for 5h;Green chemistry;	General procedure: A 10.0 mmol for alpha-keto acid compound or a 5.2 mmol for beta-diketones or alpha-keto acids was mixed with 0.40 g of hydrazinium carboxylate (1a, 5.2 mmol), respectively. (For solid di-carbonyl compound, the mixture was ground using a pestle and a mortar.) The mixture was stored in a closed vial, and then heated to 70 - 90 C until the reaction was complete. Complete conversion to related product was dependent upon the nature of di-carbonyl compounds. Typically, those di-carbonyl compounds take about <3 h to complete the reactions. CO2 and water were released during the reaction. All products obtained from the reactions of 1a with di-carbonyl compounds were basically characterized by 1H and 13C NMR spectroscopy. The products have over 97% of purity of reaction mixture based on 1H NMR spectroscopy and isolation yields are over 97% based on di-carbonyl compounds. The melting points, elemental analysis and UV-Vis spectra for all azines, pyrazoles and pyridazinones, were measured after purification using appropriate solvent.
98%	With carbazic acid; In neat (no solvent); at 90℃; for 5h;	1,3-diphenylpropane-1,3-dione using 11.22 g was 5 hours at 90 C, the rest is the same as in Example 1. The obtained compound was 3,5-diphenyl-1H-pyrazole, the selectivity was> 99%, and the yield was 98%.
88%	With hydrazine; In neat (no solvent); at 90℃; for 1h;	General procedure: A mixture of 1,3-diketone (1 mmol), hydrazine (1 mmol),and nano- SnCl4/SiO2 (0.06 g) was placed in a round bottom flask and heated at 90C for 1 hr. Progress of the reaction was followed by TLC using EtOAc/n-Hexane (ratio 2/1) as eluent. After completion of the reaction, the product was dissolved in chloroform and filtered to recover the catalyst.Then the solvent was evaporated, and the crude mixture was solidified from a mixture of ethanol and water. The pure product was obtained by recrystallization in ethanol.

79%	With titanium(IV) oxide; hydrazine; In neat (no solvent); at 60℃;Green chemistry;	General procedure: A mixture of 1,3-diketone (2 mmol), hydrazine derivatives (2mmol) and nano TiO2 (20%) was heated at 60 C. The progress of the reaction was monitored by TLC. After the completion of the reaction, the mixture was washed with chloroform and filtered to recover the catalyst. The filtrate was evaporated and the crude product was recrystallized from iso-propanol to afford the purepyrazoles derivatives in 75-92 % yields.
58%	With hydrazine hydrate; In ethanol; at 20 - 78℃; for 0.5h;	1,Dibenzoylmethane (1 eq) was added to a three-necked flask containing 50 ml of ethanol. After stirring and dissolving at room temperature, hydrazine hydrate (1 eq) was added.Then, the reaction was refluxed at 78 C for 0.5 hours. The reaction was detected by TCL, suction filtered, washed with 20 ml of ethanol, and the filter cake was recrystallized from a solvent system with a volume ratio of ethyl acetate: petroleum ether = 6: 1get3,5-diphenyl-1H-pyrazole(II-2-2),The yield is 58%,
28%	With hydrazine hydrate; In methanol; at 85℃; for 2h;	General procedure B: Preparation of a pyrazole from the requisite diketone under heated conditions The requisite diketone was dissolved in MeOH (20.0 mL) and hydrazinyl reagent added. The mixture was heated to 85 C, stirred for 2 hrs, cooled to RT then poured in H2O. EtOAc was added (50.0 mL), the aqueous and organic layers separated and the aqueous layer extracted three times with EtOAc (50.0 mL) The combined organic layers were then washed with brine (100 mL), dried over MgSO4 and concentrated in vacuo. Following standard procedure B diketone 21 (0.40 g, 1.79 mmol) and hydrazine hydrate (0.51 mL, 8.95 mmol) gave pyrazole 5. The crude product was recrystallized from DCM/heptane 4:1 (total volume 10.0 mL) to yield pyrazole 5 (0.11 g, 28%) as a white crystalline solid; 1H NMR (400 MHz, CDCl3): delta=6.85 (1H, s),7.30-7.44 (6H, m), 7.73 (4H, d, J=7.51).
	With hydrazine; In ethanol; at 60℃; for 2.5h;	Step 1: 3,5-diphenyl-1H-pyrazole, 22 is prepared as follows: Hydrazine monohydrate (2.16 mL) is added to a solution of 1,3-diphenylpropane-1,3-dione (10.0 g) in ethanol (100 mL) and the mixture is heated to 60 C. for 2.5 h forming a white precipitate over this time. Ethanol is removed in vacuo and the residue is taken up in ethyl acetate. The resulting suspension is filtered to give 3,5-diphenyl-1H-pyrazole, 22 (3.44 g) as a white powder. The filtrate is washed with water (2*100 mL), dried over magnesium sulfate and concentrated to give further 3,5-diphenyl-1H-pyrazole, 22 (5.90 g) as a solid. The compound obtained in this step shows the following mass spectral data: LC/MS: C15H12N2 requires 220.1; observed M/Z 221.3 [M-H]-, 219.4 [M-H]-. RT 4.84 min.
	With hydrazine hydrate; In ethanol; at 20℃; for 1h;	Reference Example 1 3,5-Diphenyl-1H-pyrazole To ethanol (22 mL, manufactured by Wako Pure Chemical Industries, Ltd.) solution of 1,3-diphenyl-1,3-propanedione (500 mg, manufactured by Tokyo Chemical Industry Co., Ltd.), hydrazine hydrate (228 mg, manufactured by Tokyo Chemical Industry Co., Ltd.) was added and stirred for one hour at room temperature. To the reaction solution, water (20 mL) was added followed by extraction with ethyl acetate (3*20 mL), washing with brine (20 mL) and drying over MgSO4. The solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give the title compound (480 mg). LC-MS: HPLC retention time 4.63 minutes, m/z 221(M+H), Condition A-1.
	With hydrazine hydrate; In methanol; for 2h;Reflux;	Take a 100ml round bottom flask, add magnetons, and add 1,3-diphenylpropane-1,3-dione inward. (4.49g, 20mmol, 1.0eq) And hydrazine hydrate (1.1g, 20mmol, 1.0eq), then add 50ml of methanol, Heated to reflux for 2 h, extracted with ethyl acetate and dried. Silica gel column chromatography to obtain 3,5-diphenyl 1-hydropyrazole

Reference： [1]Applied Organometallic Chemistry,2018,vol. 32
[2]Tetrahedron Letters,2013,vol. 54,p. 1384 - 1388
[3]Patent: KR101483445,2015,B1 .Location in patent: Paragraph 0290-0292
[4]Letters in Organic Chemistry,2020,vol. 17,p. 459 - 465
[5]Pakistan Journal of Scientific and Industrial Research,1993,vol. 36,p. 502 - 510
[6]Journal of the American Chemical Society,1992,vol. 114,p. 1277 - 1291
[7]Journal of the Chinese Chemical Society,2015,vol. 62,p. 17 - 20
[8]Revue Roumaine de Chimie,2016,vol. 61,p. 119 - 123
[9]Journal of Organic Chemistry,2008,vol. 73,p. 1354 - 1364
[10]Patent: CN110922359,2020,A .Location in patent: Paragraph 0039-0040; 0059-0060
[11]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2759 - 2764
[12]Chemistry Letters,1989,p. 421 - 424
[13]Journal of Organometallic Chemistry,2004,vol. 689,p. 3265 - 3274
[14]Justus Liebigs Annalen der Chemie,1899,vol. 308,p. 255
[15]Justus Liebigs Annalen der Chemie,1899,vol. 308,p. 255
[16]Patent: US2005/261354,2005,A1 .Location in patent: Page/Page column 71
[17]Patent: US2010/29690,2010,A1 .Location in patent: Page/Page column 39
[18]Inorganica Chimica Acta,2010,vol. 363,p. 1097 - 1101
[19]Dalton Transactions,2012,vol. 41,p. 3468 - 3473
[20]Molecules,2013,vol. 18,p. 4728 - 4738
[21]Organic Process Research and Development,2004,vol. 8,p. 28 - 32
[22]Journal of Coordination Chemistry,2016,vol. 69,p. 926 - 933
[23]Patent: CN108203408,2018,A .Location in patent: Paragraph 0016
[24]Catalysis Letters,2018,vol. 148,p. 2636 - 2642

14
[ 120-46-7 ]
[ 144-80-9 ]
N-acetyl-4-[N'-(1-benzoyl-2-oxo-2-phenyl-ethylidene)-hydrazino]-benzenesulfonamide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,2000,vol. 77,p. 42 - 43

15
[ 6752-16-5 ]
[ 120-46-7 ]
2,4-diphenylpyrido[2’,3’:3,4]pyrazolo[1,5-a]pyrimidine [ No CAS ]

Reference： [1]Archiv der Pharmazie,2001,vol. 334,p. 219 - 223

16
[ 120-46-7 ]
[ 104408-23-3 ]
3,5-dichloro-2-(3,5-diphenyl-pyrazol-1-yl)-pyridine [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2003,vol. 39,p. 749 - 755

17
[ 113-00-8 ]
[ 120-46-7 ]
[ 40230-24-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3134 - 3142

18
[ 84851-56-9 ]
[ 120-46-7 ]
methyl 4-(3-benzoyl-4-oxo-4-phenyl-2-butyl)benzoate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 5161 - 5167

19
[ 50-01-1 ]
[ 120-46-7 ]
[ 40230-24-8 ]

Reference： [1]Australian Journal of Chemistry,2007,vol. 60,p. 120 - 123

20
[ 403-41-8 ]
[ 120-46-7 ]
[ 960391-72-4 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sulfuric acid; In nitromethane; at 101℃; for 0.08333330000000001h;Microwave irradiation;	General procedure: beta-Dicarbonyl compound (3.0 mmol) and alcohol (1.0 mmol) were combined in 2 mL of nitromethane, and H2SO4 (2.7 muL, 0.05 mmol) was added, and the resulting mixture was stirred under 101 oC with the microwave irradiation (650 W, 70%) for 5 min. Then Na2CO3 (10 mg) was added to the reaction mixture to quench the reaction and the solvent of the reaction mixture was removed under reduced pressure and the residue was passed through the flash column chromatography on silica gel to afford the product.
97%	With silica bonded N-propylsulfamic acid; In nitromethane; at 100℃; for 0.25h;	General procedure: To a mixture of 1,3-dicarbonyl compound (2 mmol),alcohol or styrene derivatives (1 mmol), and 0.6 gSBNPSA, was added 2 cm3 nitromethane as solvent. Themixture was stirred under reflux conditions and the reactionwas followed by TLC. After completion, the mixture wasfiltered, and the remaining was washed with warm ethanolto separate catalyst and nitromethane was removed underreduced pressure. Then, the crude products were recrystallizedfrom mixture of dichloromethane and n-hexane.All the synthesized products were known and characterized by comparison of their spectral and physical data withthose reported in literature.

Reference： [1]Chinese Journal of Chemistry,2011,vol. 29,p. 2075 - 2080
[2]Tetrahedron Letters,2012,vol. 53,p. 2828 - 2832
[3]Monatshefte fur Chemie,2018,vol. 149,p. 2237 - 2244
[4]Chemistry - A European Journal,2007,vol. 13,p. 8610 - 8619
[5]Journal of Organic Chemistry,2010,vol. 75,p. 5017 - 5030

21
[ 14498-30-7 ]
[ 3264-82-2 ]
[ 120-46-7 ]
[ 58443-28-0 ]

Yield	Reaction Conditions	Operation in experiment
	In water; acetone;	EXAMPLE 1 Preparation of 2,4-diphenyl-3-benzoylpyrrole STR13 With stirring, 3.0 g of 2-phenylazirine are added dropwise to a solution of 5.6 g of dibenzoylmethane, 10 ml of acetone and 0.1 g of nickel acetylacetonate at 50° C. The mixture is then heated at reflux for 30 minutes, cooled to 20° C., and 25 ml of water are added. The precipitated crystals are filtered with suction, washed with water, and dried to constant weight. Yield: 7.8 g (96.3percent of theory) of yellow crystals. Melting point: 195°-196° C. (after recrystallisation from isopropanol).

Reference： [1]Patent: US5288776,1994,A

22
[ 120-46-7 ]
[ 454-15-9 ]
[ 1023002-49-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 547 - 550

23
[ 123-03-5 ]
[ 10025-76-0 ]
[ 120-46-7 ]
C₅H₅NC₁₆H₃₃⁽¹⁺⁾*Eu(C₁₅H₁₁O₂)4^(1-)=C₅H₅NC₁₆H₃₃{Eu(C₁₅H₁₁O₂)4} [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1964,vol. 86,p. 5125 - 5131
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Sc: MVol.D3, 5.1.15, page 192 - 210

24
[ 10099-58-8 ]
[ 120-46-7 ]
[ 1251-85-0 ]
La(C₁₅H₁₁O₂)3*C₂₃H₂₄N₄O₂ [ No CAS ]

Reference： [1]Doklady Akademii Nauk SSSR,1980,vol. 250,p. 122 - 125
C.A.,1980,vol. 92,p. 139945
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Sc: MVol.D3, 5.1.15, page 192 - 210

25
[ 10099-58-8 ]
[ 120-46-7 ]
[ 1251-85-0 ]
La{COC₆H₅NN(CH₃)C(CH₃)C}2CH₂(C₆H₅COCHCOC₆H₅)3 [ No CAS ]

Reference： [1]Doklady Chemistry,1980,vol. 250,p. 16 - 19
Dokl. Chem. (Transl. of Dokl. Akad. Nauk),1980,vol. 250,p. 122 - 125

26
[ 870-08-6 ]
[ 120-46-7 ]
[ 84887-57-0 ]

Reference： [1]Inorganic Chemistry,1982,vol. 21,p. 2283 - 2285

27
[ 123-03-5 ]
europium(III) [ No CAS ]
[ 120-46-7 ]
[Eu(PhC(O)CHC(O)Ph)4](cetylpyridinium) [ No CAS ]

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2003,vol. 59,p. 271 - 277

28
[ 4318-37-0 ]
nickel(II) nitrate hexahydrate [ No CAS ]
[ 120-46-7 ]
[nickel(II) (N-methyl-1,4-diazacycloheptane) (dibenzoylmethanate) (nitrate)] [ No CAS ]

Reference： [1]Polyhedron,2007,vol. 26,p. 1570 - 1578

29
[ 4318-37-0 ]
nickel(II) sulfate hexahydrate [ No CAS ]
[ 120-46-7 ]
[nickel(II) (N-methyl-1,4-diazacycloheptane) (dibenzoylmethanate)2] [ No CAS ]

Reference： [1]Polyhedron,2007,vol. 26,p. 1570 - 1578

30
[ 622-98-0 ]
[ 120-46-7 ]
[ 727401-27-6 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 4898 - 4903
[2]Journal of Organic Chemistry,2008,vol. 73,p. 7822 - 7825

31
[ 139756-22-2 ]
[ 120-46-7 ]
[ 876949-67-6 ]

Reference： [1]Journal of the Indian Chemical Society,2008,vol. 85,p. 1045 - 1049
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2010,vol. 49,p. 84 - 88

32
[ 86-86-2 ]
[ 120-46-7 ]
[ 1235999-34-4 ]

Reference： [1]Chinese Journal of Chemistry,2010,vol. 28,p. 670 - 672

33
[ 1004-40-6 ]
[ 555-16-8 ]
[ 120-46-7 ]
[ 1251466-51-9 ]

Reference： [1]Synthetic Communications,2010,vol. 40,p. 2788 - 2805

34
[ 623-76-7 ]
[ 120-46-7 ]
[ 98-86-2 ]
[ 1242143-88-9 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4026 - 4029

35
[ 1794-45-2 ]
[ 120-46-7 ]
[ 1313870-32-4 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 4080 - 4083

36
[ 2879-20-1 ]
[ 120-46-7 ]
2-benzoyl-4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-phenylbut-2-ene-1,4-dione [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 9865 - 9870,6

37
[ 2879-20-1 ]
[ 120-46-7 ]
[ 1403874-10-1 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 9865 - 9870,6

38
[ 120-46-7 ]
[ 118430-74-3 ]
[ 82-86-0 ]
[ 1398122-78-5 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 4894 - 4897,4

39
[ 831-81-2 ]
[ 120-46-7 ]
[ 1289648-64-1 ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 181 - 190

40
[ 2632-10-2 ]
[ 120-46-7 ]
2-benzoyl-4-(3,4-dichlorophenyl)-1-phenylbut-2-ene-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper(l) iodide; In dimethyl sulfoxide; at 20 - 90℃;Sealed tube;	General procedure: General procedure: A sealed tube was charged with alpha-iodide aromatic ketone 1a (123 mg, 0.5 mmol), dibenzoylmethane 2a (112 mg, 0.5 mmol), and CuI (47.6 mg, 0.25 mmol) at room temperature, and then dried solvent DMSO (3 mL) was added. The resulting mixture was stirred at 90 , after disappearance of the reactant (monitored by TLC), then added 50mL water to the mixture, extracted with EtOAc 3 times (3 × 50 mL). The extract was washed with 10% NaCl solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was puried by column chromatography on silica gel (petroleum ether/EtOAc = 8:1) to yield the desired product 3a as a yellow solid (85% yield).

Reference： [1]Tetrahedron,2013,vol. 69,p. 6392 - 6398

41
[ 4209-02-3 ]
[ 120-46-7 ]
[ 1434751-77-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With copper(l) iodide; In dimethyl sulfoxide; at 20 - 90℃;Sealed tube;	General procedure: General procedure: A sealed tube was charged with alpha-iodide aromatic ketone 1a (123 mg, 0.5 mmol), dibenzoylmethane 2a (112 mg, 0.5 mmol), and CuI (47.6 mg, 0.25 mmol) at room temperature, and then dried solvent DMSO (3 mL) was added. The resulting mixture was stirred at 90 , after disappearance of the reactant (monitored by TLC), then added 50mL water to the mixture, extracted with EtOAc 3 times (3 × 50 mL). The extract was washed with 10% NaCl solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was puried by column chromatography on silica gel (petroleum ether/EtOAc = 8:1) to yield the desired product 3a as a yellow solid (85% yield).

Reference： [1]Tetrahedron,2013,vol. 69,p. 6392 - 6398

42
[ 573-54-6 ]
[ 120-46-7 ]
5-nitro-3-phenyl-1H-isochromen-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium tert-butylate; copper; In tert-butyl alcohol; for 16h;Reflux;	Compound 1034 (5.0g, 20mmol) and Cu powder (150mg, 2.4mmol) were added to 17b (22.9g, 102mmol) and KOBut (4.6g, 41mmol) in ButOH (100mL). The mixture was boiled under reflux for 16h, then poured into water and acidified with aq HCl (2M). This suspension was extracted (Et2O). Evaporation and chromatography (hexane/EtOAc 10:1) gave 12b (4.2g, 78%) as yellow crystals, with data as above.
78%	With potassium tert-butylate; copper; In tert-butyl alcohol; for 16h;Reflux;	5-Nitro-3-phenylisocoumarin (3c). 1 ,3-Diphenylpropane-1 ,3-dione (22.9 g, 102 mmol) was boiled under reflux with <strong>[573-54-6]2-bromo-3-nitrobenzoic acid</strong> 285 (4.5 g, 20 mmol), potassium f-butoxide (4.6 g, 41 mmol) and copper powder (150 mg, 2.4 mmol) in 2- methylpropan-2-ol (100 mL) for 16 h. The mixture was poured into water (350 mL) and the mixture was acidified by addition of aqueous hydrochloric acid (2 M). The solution was extracted with diethyl ether. The solvent was evaporated from the extract and chromatography (hexane / ethyl acetate 10:1) gave 5-nitro-3-phenylisocoumarin 3c (4.2 g, 78%) as yellow crystals: mp 142-143C; IR vmax (KBr) 1739, 1626, 1525, 1341 cm"1; 1H NMR (CDCI3) delta 7.50-7.53 (3 H, m, Ph 3,4,5-H3), 7.62 (1 H, t, J = 7.8 Hz, 7-H), 7.89 (1 H, d, J = 0.8 Hz, 4-H), 7.93-7.97 (2 H, m, Ph 2,6-H2), 8.51 (1 H, dd, J = 8.2, 1.2 Hz, 6-H), 8.65 (1 H, ddd, J = 8.2, 1.2, 0.8 Hz, 8-H); 13C NMR (CDCI3) delta 117.18 4-C, 121.01 , 125.61 , 127.59, 127.90, 128.28, 128.77, 129.83, 131.18, 135.44, 148.42, 157.06, 165.07 (C=0); MS (electron impact) m/z 267.0532 (M)+ (C15H9N04 requires 267.0532).

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5218 - 5227
[2]Patent: WO2014/87165,2014,A1 .Location in patent: Page/Page column 48

43
[ 874-89-5 ]
[ 120-46-7 ]
4-cyanobenzyl 2-oxo-2-phenylacetate [ No CAS ]
[ 134838-29-2 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 15257 - 15262

44
dysprosium(III) chloride hexahydrate [ No CAS ]
[ 120-46-7 ]
[ 108-88-3 ]
[ 3060-50-2 ]
[Dy5(μ4-OH)(μ3-OH)4(2,2-diphenyl glycine(1-))4(dibenzoylmethanide)6]*5(C7H8)*0.5H2O [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 14794 - 14800

45
[ 7560-83-0 ]
[ 120-46-7 ]
[ 4727-98-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With oxygen; In water; dimethyl sulfoxide; at 20℃; under 760.051 Torr; for 24h;Irradiation;	General procedure: To a mixture of 1,3-diphenylpropane-1,3-dione 1a (0.5mmol) and 9/1 (v/v) DMSO/H2O (2mL) in a 10mL two-necked round-bottom flask was added N-methyl-dicyclohexanamine (0.25mmol). The resulting mixture was stirred under 1 atm of O2 (balloon) for 24 h at ambient temperature under the irradiation by three 45W white fluorescent bulbs (Arrow BHSL 45) at a distance of 5 cm. Then the reaction mixture was washed three times with dilute hydrochloric acid. Purification was done by column chromatography on silica gel (200-300 mesh) using petroleum ether and ethyl acetate (5:1-10:1) as the eluent to give the pure product 2a.

Reference： [1]Chinese Chemical Letters,2014,vol. 25,p. 545 - 548
[2]RSC Advances,2014,vol. 4,p. 26783 - 26786

46
[ 63071-10-3 ]
[ 120-46-7 ]
[ 1640100-23-7 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 29502 - 29508

47
[ 42330-59-6 ]
[ 120-46-7 ]
[ 1640100-24-8 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 29502 - 29508

48
[ 120-46-7 ]
[ 140-38-5 ]
[ 2866-82-2 ]

Reference： [1]RSC Advances,2015,vol. 5,p. 12387 - 12391

49
[ 13959-02-9 ]
[ 120-46-7 ]
[ 118160-04-6 ]

Yield	Reaction Conditions	Operation in experiment
7%	With potassium phosphate; copper(l) iodide; In N,N-dimethyl-formamide; at 100℃; for 144h;Inert atmosphere;	Compound 31 (101.5 mg, 0.5 mmol) was stirred with 37a(114 mg, 0.5 mmol), K3PO4 (212 mg, 1.0 mmol) and CuI (10 mg,50 lmol) in dry DMF (7 mL) at 100 C under Ar for 6 d. Water(7 mL) was added to the cooled mixture. The mixture was extractedEtOAc (3). The combined extracts were dried. Evaporation andchromatography (petroleum ether: EtOAc 5:1?3:1) gave 41a(7.6 mg, 7%) as a yellow powder: mp 171-173 C (lit.53 166-168 C); 1H NMR (CDCl3) d 7.02 (1H, s, 4-H), 7.48 (3H, m, Ph 3,4,5-H3), 7.89 (2H, m, Ph 2,6-H2), 8.06 (1H, d, J = 5.2 Hz, 8-H), 8.76 (1H,d, J = 5.1 Hz, 7-H), 8.97 (1H, s, 5-H); 13C NMR d 98.52 (4-C), 118.0(8-C), 125.42 (Ph 2,6-C2), 127.00 (8a-C), 129.01 (Ph 3,5-C2), 130.64(Ph 4-C), 131.00 (Ph 1-C), 132.00 (3-C), 148.44 (7-C), 149.00 (5-C),151.00 (1-C); MS m/z 224.0708 (M+H)+ (C14H10NO2 requires224.0712).

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

50
[ 13959-02-9 ]
[ 120-46-7 ]
[ 35968-87-7 ]

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

51
[ 326-91-0 ]
[ 7560-83-0 ]
[ 120-46-7 ]
2-benzoyl-1-phenyl-5-(thiophen-2-yl)pentane-1,5-dione [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 3076 - 3080

52
[ 2399-48-6 ]
[ 120-46-7 ]
(tetrahydrofuran-2-yl)methyl 5-oxo-5-phenylpentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; at 85℃; for 24h;	To the 20 mL reaction tube was added 112 mg (0.5 mmol) of compound dibenzoylmethane, 7 mg (0.025 mmol) of K2CO3, 147 muL (1 mmol) of tetrahydrofurfural acrylate and 0.5 mL of tetrahydrofurfuryl alcohol at a temperature of 85 C The reaction was stirred for 24 hours and cooled to room temperature (18-25 C) and transferred to a small flask of 10 mL. The solvent was distilled off under reduced pressure and then passed through a column of neutral alumina. The developing solvent used was petroleum ether: ethyl acetate= 13: 1 to 4: 1 to give compound III-16 126 mg in 91% yield

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 2390 - 2394
[2]Patent: CN105061125,2017,B .Location in patent: Paragraph 0090-0092

53
[ 2399-48-6 ]
[ 64-17-5 ]
[ 120-46-7 ]
[ 73172-56-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 2390 - 2394

54
[ 2495-37-6 ]
[ 120-46-7 ]
benzyl 2-methyl-5-oxo-5-phenylpentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium carbonate; In benzyl alcohol; at 85℃; for 15h;	To the 20 mL reaction tube was added 112 mg (0.5 mmol) of compound dibenzoylmethane, 7 mg (0.025 mmol) of K2CO3, 169 muL (1 mmol) of <strong>[2495-37-6]benzyl methacrylate</strong> and 0.5 mL of benzyl alcohol, and the mixture was stirred at 85 C The reaction was carried out for 15 hours and cooled to room temperature (18-25 C) and transferred to a small flask of 10 mL. The solvent was distilled off under reduced pressure and then passed through neutral alumina. The developing solvent used was petroleum ether: ethyl acetate =20: 1 to 6: 1 to give compound III-7 67 mg in 45% yield

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 2390 - 2394
[2]Patent: CN105061125,2017,B .Location in patent: Paragraph 0063-0065

55
[ 64-17-5 ]
[ 2495-37-6 ]
[ 120-46-7 ]
ethyl 2-methyl-5-oxo-5-phenylpentanoate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 2390 - 2394

56
[ 1123-86-0 ]
[ 120-46-7 ]
2-benzoyl-5-cyclohexyl-1-phenylpentane-1,5-dione [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 5623 - 5633

57
[ 1122-85-6 ]
[ 120-46-7 ]
phenyl-2-benzoyl-3-hydroxy-3-phenylacrylimidate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	In diethyl ether; at 20℃; for 40h;	General procedure: Compounds 2a-i were synthesized according to the reported method: a mixture of ethyl acetoacetate (6 mmol), <strong>[1122-85-6]phenyl cyanate</strong> (5 mmol) in diethyl ether (10 mL) at room temperature for 40 h. After completion of the reaction monitored by TLC, the volatile components were removed using a vacuum rotary evaporator. Purification by column chromatography on silica gel produced 3-hydroxybut-2-enimidates 2a-i.

Reference： [1]Tetrahedron,2016,vol. 72,p. 5749 - 5753

58
[ 2700-30-3 ]
[ 120-46-7 ]
2-(N,N-diisopropylaminoformyl)-1,3-diphenyl-propan-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With di-tert-butyl peroxide; copper(II) bis(trifluoromethanesulfonate); at 140℃;	Propan-1,3-diphenyl-1,3-dione, N, N- diisopropyl-carboxamide as a starting material, the reaction procedure was as follows:Reaction flask was added 1,3-diphenyl-propan-1,3-dione (0.224g, 1mmol), N, N- diisopropyl-formamide (2 ml), copper triflate (0.036 g, 0.1mmol) and di-t-butyl peroxide (0.292g, 2mmol), at 140 deg C reaction; TLC until complete reaction was followed over;After completion of the reaction the crude product obtained was purified by column chromatography (petroleum ether: ethyl acetate = 4: 1) to give the desired product(91% yield).

Reference： [1]Patent: CN105503635,2016,A .Location in patent: Paragraph 0043

59
[ 59194-26-2 ]
[ 120-46-7 ]
7-methoxy-4-phenylpyrrolo[1,2-a]quinoxaline [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 8529 - 8535

60
[ 120-46-7 ]
[ 1117-97-1 ]
[ 6919-61-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 3184 - 3187

61
[ 13421-00-6 ]
[ 120-46-7 ]
6-chloro-3-phenyl-1H-isochromen-1-one [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 2470 - 2473

62
[ 6962-92-1 ]
[ 120-46-7 ]
[ 100-63-0 ]
C₂₅H₂₄N₂O [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 8110 - 8113

63
[ 13275-42-8 ]
[ 120-46-7 ]
[ 21869-11-4 ]

Yield	Reaction Conditions	Operation in experiment
48%	With potassium phosphate; copper(l) iodide; In N,N-dimethyl-formamide; at 130℃; for 24h;	General procedure: To a 5mL screw-capped vial was added 1 (0.3mmol) and 1,3-diketone 2 (0.45mmol), together with CuI (0.006g, 0.03mmol), K3PO4 (0.127g, 0.6mmol), and DMF (3mL). The mixture was stirred at 130C for 24h. The mixture was then cooled to room temperature, and filtered through a short column of silica gel (ethyl acetate) to remove inorganic salts. Removal of the solvent left a crude mixture, which was separated by TLC [silica gel 60 GF254 (Merck), ethyl acetate-hexane (the reaction with acyclic ketones) or dichloromethane-methanol (the reaction with cyclic ketones)] to give desired products 3. Except for known 3o [11h], 3q [11c], 3s [11b] and 3t [10a], all new products prepared by the above procedure were characterized spectroscopically as shown below. Similar treatment of 6 with 2a and work-up (TLC, CH2Cl2/MeOH=99/1) shown above gives 7 in 56% yield.

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 5325 - 5331
[2]Journal of Organometallic Chemistry,2017,vol. 851,p. 136 - 142

64
[ 120-46-7 ]
[ 15068-35-6 ]
[ 155694-62-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate; In dimethyl sulfoxide; at 100℃; for 2h;Inert atmosphere; Sealed tube;	General procedure: 2-chlorobenzoic acids (1a, 0.2 mmol), pentane-2,4-dione (2a, 2 eq), Cu NPs (1.3 mg, 10 mol%), K2CO3 (2.0 equiv) and 1.5 mL of DMSO were added into a 5-mL sealed tube under N2. The mixture was stirred at 100 C for 2 h. The reaction mixture was then purified by flash column chromatography on silica gel (hexanes/EtOAc 15:1). Compound 3a was obtained in >92% of yield.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 3164 - 3167

65
[ 7697-25-8 ]
[ 120-46-7 ]
6-methoxy-3-phenyl-1H-isochromen-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate; In dimethyl sulfoxide; at 100℃; for 2h;Inert atmosphere; Sealed tube;	General procedure: 2-chlorobenzoic acids (1a, 0.2 mmol), pentane-2,4-dione (2a, 2 eq), Cu NPs (1.3 mg, 10 molpercent), K2CO3 (2.0 equiv) and 1.5 mL of DMSO were added into a 5-mL sealed tube under N2. The mixture was stirred at 100 °C for 2 h. The reaction mixture was then purified by flash column chromatography on silica gel (hexanes/EtOAc 15:1). Compound 3a was obtained in >92percent of yield.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 3164 - 3167

66
[ 354-64-3 ]
[ 456-14-4 ]
[ 120-46-7 ]
2-(4-fluorophenyl)-4-phenyl-5-benzoyl 6-trifluoromethylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 4h;	Put <strong>[456-14-4]4-fluorobenzamidine hydrochloride</strong> and sodium hydroxide into a 25 mL round bottom flask and inject 3 mL of N, N dimethyl Amide solvent, pretreatment and in addition to acid to give free amidine. then, Dibenzoylmethane is added at room temperature Pentafluoride iodine Ethane. Indoor lighting and room temperature reaction 4h, TLC to monitor the reaction end, stop the reaction, the mixture. [0159] molar ratio, dibenzoylmethane: pentafluoroiodoethane: 4-Fluorobenzamidine Hydrochloride: Sodium Hydroxide = 1.0: 1.1: 1.1: 4.1; [0160] 2. The mixture was extracted three times with water, the organic phases were combined, The organic solvent was removed by distillation under reduced pressure to give crude product; [0161] 3. The crude product was chromatographed on silica gel eluting with eluent (petroleum ether: ethyl acetate = 250: 1) to give A white solid was the product of 2- (4-fluorophenyl) -4-phenyl-5-benzoyl 6-trifluoromethylpyrimidine in a yield of 78percent

Reference： [1]Patent: CN106831603,2017,A .Location in patent: Paragraph 0157-0162

67
[ 4523-45-9 ]
[ 120-46-7 ]
6-methyl-2,4-diphenylbenzo[h]quinolone [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2017,vol. 35,p. 1595 - 1600

68
[ 578743-87-0 ]
[ 120-46-7 ]
1,3-bis(2,6-diisopropylphenylimidazol)-2-ylidene copper(I) dibenzoylmethanate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 9234 - 9237

69
[ 67-66-3 ]
[ 6638-05-7 ]
gadolinium(III) chloride hexahydrate [ No CAS ]
[ 120-46-7 ]
2C₇₈H₆₂Gd₂O₁₄*CHCl₃ [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2018,vol. 13,p. 1725 - 1734

70
[ 67-66-3 ]
[ 6638-05-7 ]
dysprosium(III) chloride hexahydrate [ No CAS ]
[ 120-46-7 ]
2C₇₈H₆₂Dy₂O₁₄*CHCl₃ [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2018,vol. 13,p. 1725 - 1734

71
[ 317-20-4 ]
[ 120-46-7 ]
(8-fluoro-3-phenyl-9H-[1,2]dioxino[3,4-b]indol-4-yl)(phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.2%	With dihydrogen peroxide; In N,N-dimethyl-formamide; toluene; at 110℃; for 8.5h;	132 mg (0.8 mmol) <strong>[317-20-4]7-fluoroisatin</strong>, 215.1 mg (0.96 mmol) 1,3-diphenyl-1,3-propanedione, 50 mL toluene and 5 mL DMF as solvent, 1 mL H2O2, and 20 mg strong acid ion exchange resin D001 as catalyst were added to a 100 mL round flask. The mixture was stirred and heated at 110 C. for 8.5 hours. The reaction was monitored with TLC. When TLC indicated that reaction was complete, heating was removed. The reaction mixture was concentrated, filtered, and purified by fresh chromatograph to obtain 190.6 mg desired product (compound 12), a yield of 64.2%. 1H-NMR (300 MHz, DMSO-d6) delta (ppm): 10.89 (1H, s), 7.68?7.85 (5H, m), 7.22?7.67 (5H, m), 7.14 (1H, d), 6.85 (1H, d), 6.75 (1H, t); 13C-NMR (75 MHz, DMSO-d6) delta (ppm): 169.2, 167.5, 153.2, 148.9, 136.5, 134.5, 132.7, 130.3, 129.2, 128.8, 127.9, 122.1, 118.4, 108.5, 100.9, 93.3; MS (ESI) for (M+Na)+: 394.1.
64.2%	With dihydrogen peroxide; In N,N-dimethyl-formamide; toluene; at 110℃; for 8.5h;	Is added to the reactor 132 mg (0.8 mmol) 7 - fluoro - isatin and 215.1 mg (0.96 mmol) 1, 3 - diphenyl - 1, 3 - c diketone, add 50 ml toluene and 5 ml DMF as the reaction solvent, adding 1 ml H2O2And the catalytic amount of the strong acid ion resin D001 as catalyst, electric jacket heated to 110 C, magnetic stirring reflux reaction for 8.5 hours. Thin-layer chromatographic trace to after the reaction is complete, evaporating the solvent under reduced pressure,, the resulting mixture by silica gel column chromatography separation and purification, drying to obtain the target compound 190.6 mg, total yield 64.2%.

Reference： [1]Patent: US10035808,2018,B1 .Location in patent: Page/Page column 12; 13
[2]Patent: CN108558895,2018,A .Location in patent: Paragraph 0049; 0050

72
[ 7335-06-0 ]
praseodymium (III) chloride heptahydrate [ No CAS ]
[ 120-46-7 ]
[C₄H₈NEtH][Pr(dibenzoylmethanate)₄] [ No CAS ]