[ CAS No. 611-73-4 ] {[proInfo.proName]}

Name: 611-73-4|2-Oxo-2-phenylacetic acid|95%
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Quality Control of [ 611-73-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 611-73-4 ]

Product Details of [ 611-73-4 ]

CAS No. :	611-73-4	MDL No. :	MFCD00002575
Formula :	C₈H₆O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FAQJJMHZNSSFSM-UHFFFAOYSA-N
M.W :	150.13	Pubchem ID :	11915
Synonyms :	Benzoylformic acid	Chemical Name :	2-Oxo-2-phenylacetic acid

Calculated chemistry of [ 611-73-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	38.41
TPSA :	54.37 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.91
Log Po/w (XLOGP3) :	1.33
Log Po/w (WLOGP) :	0.95
Log Po/w (MLOGP) :	0.7
Log Po/w (SILICOS-IT) :	1.08
Consensus Log Po/w :	0.99

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.88
Solubility :	1.98 mg/ml ; 0.0132 mol/l
Class :	Very soluble
Log S (Ali) :	-2.07
Solubility :	1.27 mg/ml ; 0.00845 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.7
Solubility :	2.99 mg/ml ; 0.0199 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.03

Safety of [ 611-73-4 ]

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

Application In Synthesis of [ 611-73-4 ]

* 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 [ 611-73-4 ]
Downstream synthetic route of [ 611-73-4 ]

[ 611-73-4 ] Synthesis Path-Upstream 1~10

1
[ 150-13-0 ]
[ 611-73-4 ]
[ 582-80-9 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 13, p. 3114 - 3117

2
[ 611-73-4 ]
[ 41394-05-2 ]

Reference： [1] Patent: CN106187929, 2016, A,

3
[ 424792-60-9 ]
[ 611-73-4 ]
[ 4335-77-7 ]

Reference： [1] Patent: US2003/13911, 2003, A1,

4
[ 55499-43-9 ]
[ 611-73-4 ]
[ 2571-39-3 ]

Reference： [1] RSC Advances, 2014, vol. 4, # 89, p. 48698 - 48702

5
[ 586-96-9 ]
[ 611-73-4 ]
[ 304-88-1 ]

Reference： [1] Journal of Organic Chemistry, 1989, vol. 54, # 18, p. 4449 - 4453

6
[ 611-73-4 ]
[ 21210-43-5 ]

Reference： [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 20, p. 3665 - 3673
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 20, p. 3665 - 3673

7
[ 611-73-4 ]
[ 7322-88-5 ]
[ 51019-43-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 20, p. 3665 - 3673
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 20, p. 3665 - 3673

8
[ 611-73-4 ]
[ 7322-88-5 ]
[ 51019-43-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 20, p. 3665 - 3673
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 20, p. 3665 - 3673

9
[ 56-89-3 ]
[ 7732-18-5 ]
[ 611-73-4 ]
[ 3342-78-7 ]

Reference： [1] Journal of the American Chemical Society, 1936, vol. 58, p. 2241

10
[ 611-73-4 ]
[ 521284-19-5 ]

Reference： [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 20, p. 3665 - 3673

[ 611-73-4 ] Synthesis Path-Downstream 1~88

1
[ 110-89-4 ]
[ 939-79-7 ]
[ 611-73-4 ]
[ 61599-55-1 ]

Reference： [1]Chemische Berichte,1911,vol. 44,p. 1122
[2]Chemische Berichte,1911,vol. 44,p. 1122

2
[ 939-79-7 ]
[ 611-73-4 ]
[ 61599-55-1 ]

Reference： [1]Chemische Berichte,1911,vol. 44,p. 1122

3
[ 25148-68-9 ]
[ 611-73-4 ]
[ 2048-37-5 ]

Reference： [1]Helvetica Chimica Acta,1952,vol. 35,p. 2301,2308

4
[ 611-73-4 ]
[ 33240-34-5 ]
[ 427-49-6 ]

Yield	Reaction Conditions	Operation in experiment
36.4%	In diethyl ether; at 0 - 20℃; for 24.5h;	Cyclopentylmagnesium bromide ether solution (100 ml, 2M; 0.2 mol) was added drop-wise to benzoylformic acid (15 g, 0.1 mol) in 330 ml of anhydrous ethyl ether at 0 C. The mixture was stirred at 0 C. for 30 min and at room temperature for 24 h. The reaction mixture was treated with 1 N HCl, and the aqueous solution was extracted with ether. The combined ether solution was treated with K2CO3 solution. The potassium carbonate solution was acidified with HCl and extracted with ether twice. The ether solution was dried with anhydrous sodium sulfate and evaporated to give a crude product. The crude product was washed with water to get pure racemic cyclopentylmandelic acid 1 (8.0 g, 36.4%). Needle-like crystal, m.p.: 153-154 C. 1H NMR (CDCl3,300 MHz): 1.28-1.39, 1.42-1.50, 1.51-1.61, 1.63-1.72 [8H, m, (CH2)4], 2.93 [1H, p, CHC(OH)], 7.26-7.30, 7.33-7.36, 7.65-7.67(5H, m, Ph) ppm.; Cyclopentylmagnesium bromide ether solution (100 ml, 2M; 0.2 mol) was added drop-wise to benzoylformic acid (15 g, 0.1 mol) in 330 ml of anhydrous ethyl ether at 0 C. The mixture was stirred at 0 C. for 30 min and at room temperature for 24 h. The reaction mixture was treated with 1 N HCl, and the aqueous solution was extracted with ether. The combined ether solution was treated with K2CO3 solution. The potassium carbonate solution was acidified with HCl and extracted with ether twice. The ether solution was dried with anhydrous sodium sulfate and evaporated to give a crude product. The crude product was washed with water to get pure racemic cyclopentylmandelic acid 1 (8.0 g, 36.4%). Needle-like crystals, m.p.: 153-154 C. 1H NMR (CDCl3, 500 MHz): 1.28-1.39, 1.42-1.50, 1.51-1.61, 1.63-1.72 [8H, m, (CH2)4], 2.93 [1H, p, CHC(OH)], 7.26-7.30, 7.33-7.36, 7.65-7.67(5H, m, Ph) ppm.

Reference： [1]Patent: US2007/123557,2007,A1 .Location in patent: Page/Page column 9; 12; 15-16
[2]Pharmazie,2008,vol. 63,p. 200 - 209
[3]Journal of the American Chemical Society,1959,vol. 81,p. 2214,2218

5
[ 25911-65-3 ]
[ 611-73-4 ]
2-amino-6-benzoyl-3-cyanopyrazine [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1992,vol. 29,p. 1685 - 1688

6
[ 68817-71-0 ]
[ 611-73-4 ]
[ 74769-98-5 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 17 1-(4-Chlorophenyl)-1,2-dihydro-3-phenylquinoxalin-2-one To a solution of N-(4-chlorophenyl)benzene-1,2-diamine (12.0 g) in a minimum quantity of ether was added benzoylformic acid (7.5 g) dissolved in ether and the mixture was stirred for 8 hours. The resulting precipitate was filtered, dried, and recrystallized from ethanol giving the title compound (11.0 g) mp 214.5-216.5 C. Analysis: 71.9%C; 4.2%H; 8.3%N; Requires: 72.2%C; 3.9%H; 8.4%N.

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 1341 - 1344
[2]Patent: US4296114,1981,A

7
[ 33305-75-8 ]
[ 611-73-4 ]
[ 97409-49-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 769 - 772

8
[ 611-73-4 ]
[ 17231-51-5 ]
2-amino-6-benzoyl-5-bromo-3-cyanopyrazine [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1992,vol. 29,p. 1685 - 1688

9
[ 699-12-7 ]
[ 611-73-4 ]
[ 197861-98-6 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 7827 - 7831

10
[ 52-90-4 ]
[ 7664-41-7 ]
[ 611-73-4 ]
[ 56-89-3 ]
[ 2835-06-5 ]

Reference： [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1927,vol. 170,p. 199

11
[ 63038-27-7 ]
[ 611-73-4 ]
(S)-3,3-Dimethyl-2-(2-oxo-2-phenyl-acetylamino)-butyric acid methyl ester [ No CAS ]

Reference： [1]Synlett,2002,p. 131 - 133

12
[ 88333-03-3 ]
[ 13949-93-4 ]
[ 146651-75-4 ]
[ 611-73-4 ]
2-{benzylcarbamoyl-[(2-<i>tert</i>-butoxycarbonylamino-phenyl)-(oxo-phenyl-acetyl)-amino]-methyl}-cyclopropanecarboxylic acid ethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 1637 - 1639

13
[ 15799-79-8 ]
[ 122775-35-3 ]
[ 611-73-4 ]
(3,4-dimethoxy-phenyl)-(4-dimethylamino-2-methoxy-phenyl)-phenyl-acetic acid [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 5819 - 5821

14
[ 931-53-3 ]
[ 611-73-4 ]
[ 110-20-3 ]
N-cyclohexyl-2-[N'-carbamoyl-N-(2-oxo-2-phenylacetyl)hydrazino]isobutyramide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 4578 - 4584

15
methyl (S)-2-(benzoylformyloxy)propionate [ No CAS ]
[ 424792-60-9 ]
[ 611-73-4 ]
[ 4335-77-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide;palladium-carbon; titanium tetrachloride; In methanol; water; hydrogen; chlorobenzene; toluene; cyclohexene;	The obtained methyl (S)-2-(benzoylformyloxy)propionate (7.4 g) was dissolved in monochlorobenzene (74 ml), and cyclohexene (5.2 g) and titanium tetrachloride (7.8 g) were added. The reaction mixture was stirred at 20-25 C. for 15 h. The reaction mixture was poured into 6N hydrochloric acid (74 ml) and extracted with toluene (37 ml). The extract was washed with 6N hydrochloric acid (37 ml). To the organic layer were added 25% aqueous sodium hydroxide solution (20 g) and methanol (74 ml) and the reaction mixture was stirred at 60-65 C. for 2 h. Water (74 ml) and toluene (74 ml) were added to the reaction mixture and the partitioned organic layer was combined with the extract obtained by extracting the aqueous layer again with toluene (74 ml) and concentrated. 6N Hydrochloric acid (29 g) was added to the concentrated residue and the mixture was extracted with ethyl acetate (74 ml). The organic layer was washed with water and concentrated to give a diastereomer mixture (5.2 g) of crude optically active 2-(2'-cyclohexen-1'-yl)-2-hydroxy-2-phenylacetic acid. This (4.1 g) was dissolved in methanol (40 ml) and 5% palladium carbon (Kawaken Fine Chemicals Co., Ltd., type M, 3 g) was added. The mixture was stirred at atmospheric pressure in a hydrogen gas for 15 min. The catalyst was filtered off and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate) to give the title compound (3.3 g, yield from benzoylformic acid: 31%). This was amidated with (S)-phenylethylamine by a conventional method and the optical purity was measured by HPLC, which was found to be 22% e.e.

Reference： [1]Patent: US2003/13911,2003,A1

16
[ 32202-61-2 ]
[ 611-73-4 ]
[ 1046786-77-9 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 6506 - 6512

17
[ 59434-19-4 ]
[ 611-73-4 ]
[ 1207455-13-7 ]

Yield	Reaction Conditions	Operation in experiment
66%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In dichloromethane; at 20℃;	To a solution of <strong>[59434-19-4]4-aminoisobenzofuran-1(3H)-one</strong> (4.0 g, 26.8 mmol), 2-oxo-2-phenylacetic acid (4.1 g, 26.8 mmol), and HBTU (15.2 g, 40.2 mmol) in dichloromethane (240 mL) was added TEA (8 mL). The reaction mixture was stirred at room temperature overnight. The resulting mixture was added water and adjusted to pH=6-7 with 1% aq. HCl, and then was filtered. The filtrate was extracted with ethyl acetate. The ethyl acetate layer was evaporated and the crude product was purified by gradient chromatography (silica gel, petroleum ether/ethyl acetate 6:1 to 3:1) to give the title compound (5.0 g, yield 66%). LC-MS (ESI) m/z: 282(M+1)+.
66%		Example 1 18A2-Oxo-N-(l-oxo- l,3-dihydroisobenzofuran-4-yl)-2-phenylacetamide[00735] To a solution of 4-aminoisobenzofuran-l(3H)-one (4.0 g, 26.8 mmol), 2-oxo-2-phenylacetic acid (4.1 g, 26.8 mmol), and HBTU (15.2 g, 40.2 mmol) in dichloromethane (240 mL) was added TEA (8 mL). The reaction mixture was stirred at room temperature overnight. The resulting mixture was added water and adjusted to pH 6-7 with 1% aq. HCl, and then was filtered. The filtrate was extracted with ethyl acetate. The ethyl acetate layer was evaporated and the crude product was purified by gradient chromatography (silica gel, petroleum ether / ethyl acetate 6: 1 to 3: 1) to give the title compound (5.0 g, yield 66%). LC-MS (ESI) m/z: 282(M+1)+.

Reference： [1]Patent: US2010/35883,2010,A1 .Location in patent: Page/Page column 87
[2]Patent: WO2011/130661,2011,A1 .Location in patent: Page/Page column 169-170

18
[ 611-73-4 ]
potassium trifluoro(3-chlorophenyl)borate [ No CAS ]
[ 1016-78-0 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 2062 - 2064

19
[ 3418-21-1 ]
[ 611-73-4 ]

Reference： [1]Asian Journal of Chemistry,2012,vol. 24,p. 4979 - 4985

20
[ 27257-15-4 ]
[ 611-73-4 ]
[ 1426654-57-0 ]

Reference： [1]Green Chemistry,2016,vol. 18,p. 1201 - 1205
[2]Chemical Communications,2013,vol. 49,p. 2368 - 2370

21
[ 4783-68-0 ]
[ 611-73-4 ]
[ 1173294-85-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1517 - 1522

22
[ 4783-68-0 ]
[ 611-73-4 ]
[ 117-99-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1517 - 1522

23
[ 5193-03-3 ]
[ 611-73-4 ]
C₁₃H₉ClN₃O₂^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Derivatives 8a-g (45.4 mmol) were dissolved in EtOH (30.0 mL). Arylhydrazine derivatives 9a-g (45.4 mmol) were added, and the mixture was stirred at 25 C for 1-8 h (Table 5) (TLC monitoring, n-hexanes-EtOAc, 7:3). Then Na2CO3 (2.4 g, 22.7 mmol) was added and the mixture was stirred at 25 C for 2 h. The solid precipitate was filtered off, washed with EtOH, and dried in a vacuum drier. Compounds 10a-g were obtained as yellow solids and used in the next step without purification.

Reference： [1]Synthesis,2013,vol. 45,p. 2447 - 2457

24
[ 611-73-4 ]
[ 501-60-0 ]
[ 1421276-37-0 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 14432 - 14436

25
[ 611-73-4 ]
[ 501-60-0 ]
(E)-[5-methyl-2-(para-tolyldiazenyl)phenyl](phenyl)methanone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 10414 - 10420

26
[ 132244-31-6 ]
[ 611-73-4 ]
[ 1598429-83-4 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 8720 - 8722

27
[ 10531-80-3 ]
[ 611-73-4 ]
[ 62103-88-2 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 16705 - 16709
[2]RSC Advances,2014,vol. 4,p. 8720 - 8722

28
[ 611-73-4 ]
[ 62173-99-3 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 4489 - 4491
[2]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3991 - 3997

29
[ 10531-80-3 ]
[ 611-73-4 ]
[ 1530878-10-4 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 7241 - 7244
[2]Journal of Organic Chemistry,2015,vol. 80,p. 11065 - 11072

30
[ 375369-14-5 ]
[ 611-73-4 ]
[ 1638125-48-0 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 11065 - 11072
[2]Chemistry - A European Journal,2014,vol. 20,p. 7241 - 7244

31
[ 132244-31-6 ]
[ 611-73-4 ]
[ 1638125-49-1 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 11065 - 11072
[2]Chemistry - A European Journal,2014,vol. 20,p. 7241 - 7244

32
[ 611-73-4 ]
[ 118994-89-1 ]
ethyl 2-benzoyloxazole-5-carboxylate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 7241 - 7244
[2]Journal of Organic Chemistry,2015,vol. 80,p. 11065 - 11072

33
[ 70886-33-8 ]
[ 611-73-4 ]
[ 7653-47-6 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 16705 - 16709

34
[ 1267217-46-8 ]
[ 611-73-4 ]
[ 1602493-36-6 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 16705 - 16709

35
[ 16078-30-1 ]
[ 611-73-4 ]
[ 28748-93-8 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 14249 - 14252

36
[ 16078-30-1 ]
[ 611-73-4 ]
(E)-butyl 3-(2-(1-acetylindoline-7-carbonyl)phenyl)acrylate [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 14249 - 14252

37
[ 768-52-5 ]
[ 611-73-4 ]
[ 84711-83-1 ]

Yield	Reaction Conditions	Operation in experiment
35.4%		To a CH2Cl2 solution (20mL) of benzoylformic acid (3.00g, 30.0mmol) prepared from methyl benzoylformate by basic hydrolysis with aqueous NaOH solution (quantitative) was added catalytic amount of DMF (1 drop) and oxalyl chloride (1.9mL, 22.0mmol). The reaction mixture was stirred for 4h at room temperature until generation of gases stopped and then cooled to 0C. To this was added a solution of <strong>[768-52-5]N-isopropylanilin</strong> (3.2mL, 29.9mmol) and Et3N (7.0mL, 50.2mmol). The reaction mixture was stirred at room temperature for 1h and then quenched by adding water. Organic materials were extracted 3 times with ethyl acetate, and then the combined extracts were washed successively with a 5% HCl aqueous solution and saturated NaCl solution, dried over anhydrous MgSO4, evaporated to give the corresponding product, and recrystallized from ethyl acetate to give colorless crystals. Yield: 35.4%. lH NMR (300MHz, CDCl3): delta 1.22-1.24 (d, 6H, J=6.0Hz), 5.01-5.15 (m, 1H, J=6.0Hz), 7.05-7.78 (m, 10H). 13C NMR (300MHz, CDCl3): delta 21.2, 47.0, 128.8, 129.1, 129.4, 131.2, 133.8, 134.2, 135.7, 166.8, 190.0. Anal. calcd. for C17H17NO2: C, 76.38; H, 6.41; N, 5.24%. Found: C, 75.89; H, 6.50; N, 5.16.

Reference： [1]Chinese Chemical Letters,2015,vol. 26,p. 21 - 25

38
[ 939-57-1 ]
[ 611-73-4 ]
[ 22966-01-4 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 3586 - 3596

39
[ 20595-30-6 ]
[ 611-73-4 ]
[ 1608-52-2 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 3586 - 3596

40
[ 13026-23-8 ]
[ 611-73-4 ]
[ 36047-01-5 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 3586 - 3596

41
[ 1074-12-0 ]
[ 88333-03-3 ]
[ 69409-98-9 ]
[ 611-73-4 ]
C₃₁H₂₁F₄N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%		General procedure: General procedures for compounds 10 and 15 are as follows:a solution of aldehyde (0.50 mmol) and amine (0.50 mmol)in MeOH (1 mL) was stirred at room temperature for 10min in a 5 mL microwave vial. Next, acid (0.50 mmol) andisonitrile (0.50 mmol) were added separately. The mixturewas stirred at room temperature overnight. The reaction wasmonitored by TLC and the solvent was removed under nitrogenblowing. The residue was dissolved in AcOH (3 mL)and NH4AcO (2.5 mmol, 193 mg) was added and thentreated in microwave (MW) at 150 C for 10 min. The solventwas removed under reduced pressure and the residuewas diluted with EtOAc (15 mL) and washed with sat. sodiumcarbonate and brine. The organic layer was dried overMgSO4 and concentrated. The residue was purified by silicagel column chromatography using a gradient of ethylacetate/hexane (1%-100%) to afford the relative products 9and 14a-14h.

Reference： [1]Science China Chemistry,2015,vol. 58,p. 1239 - 1242

42
[ 1074-12-0 ]
[ 88333-03-3 ]
[ 69409-98-9 ]
[ 611-73-4 ]
C₃₁H₂₀F₃N₃O₂ [ No CAS ]

Reference： [1]Science China Chemistry,2015,vol. 58,p. 1239 - 1242

43
[ 931-53-3 ]
[ 1074-12-0 ]
[ 69409-98-9 ]
[ 611-73-4 ]
C₃₀H₂₅F₄N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%		General procedure: General procedures for compounds 10 and 15 are as follows:a solution of aldehyde (0.50 mmol) and amine (0.50 mmol)in MeOH (1 mL) was stirred at room temperature for 10min in a 5 mL microwave vial. Next, acid (0.50 mmol) andisonitrile (0.50 mmol) were added separately. The mixturewas stirred at room temperature overnight. The reaction wasmonitored by TLC and the solvent was removed under nitrogenblowing. The residue was dissolved in AcOH (3 mL)and NH4AcO (2.5 mmol, 193 mg) was added and thentreated in microwave (MW) at 150 C for 10 min. The solventwas removed under reduced pressure and the residuewas diluted with EtOAc (15 mL) and washed with sat. sodiumcarbonate and brine. The organic layer was dried overMgSO4 and concentrated. The residue was purified by silicagel column chromatography using a gradient of ethylacetate/hexane (1%-100%) to afford the relative products 9and 14a-14h.

Reference： [1]Science China Chemistry,2015,vol. 58,p. 1239 - 1242

44
[ 931-53-3 ]
[ 1074-12-0 ]
[ 69409-98-9 ]
[ 611-73-4 ]
C₃₀H₂₄F₃N₃O₂ [ No CAS ]

Reference： [1]Science China Chemistry,2015,vol. 58,p. 1239 - 1242

45
[ 611-73-4 ]
[ 436799-33-6 ]
phenyl(5-(trifluoromethyl)pyridin-3-yl)methanone [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 7929 - 7933
Angew. Chem.,2015,vol. 127,p. 8040 - 8044,5

46
[ 5093-70-9 ]
[ 611-73-4 ]
[ 59576-38-4 ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 7929 - 7933
Angew. Chem.,2015,vol. 127,p. 8040 - 8044,5

47
[ 19806-17-8 ]
[ 611-73-4 ]
[ 104595-15-5 ]

Reference： [1]New Journal of Chemistry,2016,vol. 40,p. 113 - 121

48
[ 21745-41-5 ]
[ 611-73-4 ]
[ 71635-98-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 1975 - 1981

49
[ 150-13-0 ]
[ 611-73-4 ]
[ 582-80-9 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 3114 - 3117

50
[ 4139-61-1 ]
[ 611-73-4 ]
8-bromo-3-[2-(5-bromo-2-hydroxyphenyl)-2-oxoethyl]-3-phenyl-2H-furo[3,2-c]chromene-2,4(3H)-dione [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 4907 - 4915

51
[ 455-67-4 ]
[ 611-73-4 ]
1-(3-fluorophenyl)-1-oxopropan-2-yl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In ethyl acetate; at 80℃; for 24h;Sealed tube;	General procedure: The mixture of phenylglyoxylic acid (0.2mmol), propiophenone (0.2mmol), TBHP (0.4mmol), TBAI (0.04mmol) and ethyl acetate (2mL) was stirred at 80C for 24h in a 15mL sealed tube successively. After cooling down, the reaction mixture was washed with Na2S2O3 solution, and extracted by ethyl acetate for three times. The obtained top organic layer was dried with anhydrous MgSO4. After drying, the mixture was concentrated under vacuum, and the crude product was purified by column chromatography on silica gel with petroleum ether-ethyl acetate (50:1) as eluent.

Reference： [1]Tetrahedron,2016,vol. 72,p. 7003 - 7007

52
[ 17408-16-1 ]
[ 611-73-4 ]
1-(3-nitrophenyl)-1-oxopropan-2-yl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In ethyl acetate; at 80℃; for 24h;Sealed tube;	General procedure: The mixture of phenylglyoxylic acid (0.2mmol), propiophenone (0.2mmol), TBHP (0.4mmol), TBAI (0.04mmol) and ethyl acetate (2mL) was stirred at 80C for 24h in a 15mL sealed tube successively. After cooling down, the reaction mixture was washed with Na2S2O3 solution, and extracted by ethyl acetate for three times. The obtained top organic layer was dried with anhydrous MgSO4. After drying, the mixture was concentrated under vacuum, and the crude product was purified by column chromatography on silica gel with petroleum ether-ethyl acetate (50:1) as eluent.

Reference： [1]Tetrahedron,2016,vol. 72,p. 7003 - 7007

53
[ 387-44-0 ]
[ 611-73-4 ]
(7-fluoro-1H-indol-3-yl)(phenyl)methanone [ No CAS ]

Reference： [1]Green Chemistry,2016,vol. 18,p. 4916 - 4923

54
[ 611-73-4 ]
[ 41394-05-2 ]

Reference： [1]Patent: CN106187929,2016,A

55
[ 2065-37-4 ]
[ 611-73-4 ]
2-benzoyl-3-bromonaphthalene-1,4-dione [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 8309 - 8316

56
[ 84964-24-9 ]
[ 611-73-4 ]
7-(3-bromophenyl)-3-phenyl-5,6,7,7a-tetrahydrofuro[2,3-b]pyridin-2(4H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With dmap; iron(III) chloride; di-tert-butyl peroxide; oxygen; In acetonitrile; at 60℃; for 24h;	In the reaction tube by sequentially adding a 1 e (0.5 mmol, 120 mg), 2 a (0.5 mmol, 75 mg), acetonitrile (3 ml), ferric chloride (0.05 mmol, 8.1 mg), di-tert-butyl peroxide (0.5 mmol, 92 mul) and 4 - dimethylamino pyridine (0.05 mmol, 6.1 mg), in oxygen (1 atm) atmosphere at 60 C stirring reaction 24 h. Then, by adding 10 ml saturated salt water quenching reaction, extracted with ethyl acetate (10 ml × 3), combined with the organic phase, dried with anhydrous sodium sulfate. Filtering, turns on lathe does, too separating by silica gel column (petroleum ether/ethyl acetate=10/1) to obtain white solid product 3 e (101 mg, 55%). The compound of the characterization data are as follows:

Reference： [1]Patent: CN107501278,2017,A .Location in patent: Paragraph 0071; 0072; 0073
[2]Advanced Synthesis and Catalysis,2018,vol. 360,p. 261 - 266

57
[ 43038-36-4 ]
[ 611-73-4 ]
[ 1874-33-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate; In N,N-dimethyl-formamide; at 25℃; for 24h;Sealed tube; Irradiation;	General procedure: A sealed tube equipped with a magnetic stir bar was charged with acylhydrazine 1 (0.5 mmol), alpha-keto acid 2 (0.5 mmol), K2CO3 (1 mmol), PANI-g-C3N4-TiO2 (40 mg) and DMF (5.0 mL). The mixture was then irradiated with a 14 W CFL and stirred at room temperature (25 C) for 24 h. The distance of the reaction vial from the light is about 5 centimeters. After reaction, the mixture was diluted with EtOAc (10 mL) and H2O (5 mL), and the solid catalyst was recovered by centrifugation. The aqueous phase was extracted with EtOAc (5 mL × 3). The collected organic extracts were dried on Na2SO4, filtered and evaporated to dryness. The crude was purified by flash chromatography on silica gel using a mixture of PE/EA (20:1) to give the pure product 3.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 1489 - 1492
[2]European Journal of Organic Chemistry,2020

58
[ 84964-24-9 ]
[ 611-73-4 ]
(1-(3-bromophenyl)-1,4,5,6-tetrahydropyridin-3-yl)(phenyl)-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With di-tert-butyl peroxide; copper(ll) bromide; In acetonitrile; at 60℃; under 760.051 Torr; for 24h;	In the reaction tube by sequentially adding a 1 e (0.5 mmol, 120 mg), 2 a (0.6 mmol, 90 mg), acetonitrile (3 ml), copper bromide (0.05 mmol, 11 mg) and di-tert-butyl peroxide (1 mmol, 183 mul), in air (1 atm) atmosphere at 60 C stirring reaction 24 h. Then add 10 ml saturated salt water quenching reaction, extracted with ethyl acetate (10 ml × 3), combined with the organic phase, dried with anhydrous sodium sulfate. Filtering, turns on lathe does, too separating by silica gel column (petroleum ether/ethyl acetate=5/1) to get the yellow solid product 3 e (109 mg, 64%).

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 6524 - 6533
[2]Patent: CN108516952,2018,A .Location in patent: Paragraph 0068-0070

59
[ 92-53-5 ]
[ 611-73-4 ]
phenyl(4-phenyl-3,4-dihydro-2H-1,4-oxazin-6-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With di-tert-butyl peroxide; copper(ll) bromide; In acetonitrile; at 60℃; under 760.051 Torr; for 24h;	In the reaction tube by sequentially adding a 1aa (0.5 mmol, 82 mg), 2a (0.6 mmol, 90 mg), acetonitrile (3 ml), copper bromide (0.05 mmol, 11 mg) and di-tert-butyl peroxide (1 mmol, 183 mul), in air (1 atm) atmosphere at 60 C stirring reaction 24 h. Then add 10 ml saturated salt water quenching reaction, extracted with ethyl acetate (10 ml × 3), combined with the organic phase, dried with anhydrous sodium sulfate. Filtering, turns on lathe does, too separating by silica gel column (petroleum ether/ethyl acetate=5/1) to get the yellow solid product 3aa (86 mg, 65%).

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 6524 - 6533
[2]Patent: CN108516952,2018,A .Location in patent: Paragraph 0116-0118

60
[ 611-73-4 ]
[ 3964-04-3 ]
(4-bromoquinolin-2-yl)(phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With ammonium peroxydisulfate; [Ir(2-(2,4-difluorophenyl)-5-methylpyridine)2(4,4?-di-tert-butyl-2,2?-bipyridine)]PF6; In dimethyl sulfoxide; at 20℃; for 12h;Inert atmosphere; Irradiation; Green chemistry;	General procedure: Heterocycle (0.10mmol, 1 equiv)ammonium persulfate (0.20 mmol, 2equiv),[Ir{dF(CF3ppy)}2(dtbbpy)]PF6 ( 0.2 mol%),alpha-keto acids(1.0mmol10equiv)wereplaced in a dry glass tube.Then, anhydrous DMSO1mLwereinjected into the tubeby syringe under a N2 atmosphere.The solution was then stirred at roomtemperatureunder the irradiation of 15W blue LEDs strip for 12h.After completion of thereaction,then saturated Na2CO3solution was added to adjust pH to basic.Thecombined organic layer was washed with brine and then dried overanhydrousNa2SO4.The desired products were obtained in thecorresponding yields afterpurification by flashchromatography on silica gel eluting with petroleum andethylacetate.

Reference： [1]Organic Letters,2018,vol. 20,p. 4686 - 4690
[2]Synlett,2018,vol. 29,p. 1881 - 1886

61
[ 34784-07-1 ]
[ 611-73-4 ]
(8-chloroisoquinolin-1-yl)(phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With ammonium peroxydisulfate; [Ir(2-(2,4-difluorophenyl)-5-methylpyridine)2(4,4?-di-tert-butyl-2,2?-bipyridine)]PF6; In dimethyl sulfoxide; at 20℃; for 12h;Inert atmosphere; Irradiation; Green chemistry;	General procedure: Heterocycle (0.10mmol, 1 equiv)ammonium persulfate (0.20 mmol, 2equiv),[Ir{dF(CF3ppy)}2(dtbbpy)]PF6 ( 0.2 mol%),alpha-keto acids(1.0mmol10equiv)wereplaced in a dry glass tube.Then, anhydrous DMSO1mLwereinjected into the tubeby syringe under a N2 atmosphere.The solution was then stirred at roomtemperatureunder the irradiation of 15W blue LEDs strip for 12h.After completion of thereaction,then saturated Na2CO3solution was added to adjust pH to basic.Thecombined organic layer was washed with brine and then dried overanhydrousNa2SO4.The desired products were obtained in thecorresponding yields afterpurification by flashchromatography on silica gel eluting with petroleum andethylacetate.

Reference： [1]Synlett,2018,vol. 29,p. 1881 - 1886

62
[ 27104-73-0 ]
[ 611-73-4 ]
methyl 1-benzoylisoquinoline-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With ammonium peroxydisulfate; [Ir(2-(2,4-difluorophenyl)-5-methylpyridine)2(4,4?-di-tert-butyl-2,2?-bipyridine)]PF6; In dimethyl sulfoxide; at 20℃; for 12h;Inert atmosphere; Irradiation; Green chemistry;	General procedure: Heterocycle (0.10mmol, 1 equiv)ammonium persulfate (0.20 mmol, 2equiv),[Ir{dF(CF3ppy)}2(dtbbpy)]PF6 ( 0.2 mol%),alpha-keto acids(1.0mmol10equiv)wereplaced in a dry glass tube.Then, anhydrous DMSO1mLwereinjected into the tubeby syringe under a N2 atmosphere.The solution was then stirred at roomtemperatureunder the irradiation of 15W blue LEDs strip for 12h.After completion of thereaction,then saturated Na2CO3solution was added to adjust pH to basic.Thecombined organic layer was washed with brine and then dried overanhydrousNa2SO4.The desired products were obtained in thecorresponding yields afterpurification by flashchromatography on silica gel eluting with petroleum andethylacetate.

Reference： [1]Synlett,2018,vol. 29,p. 1881 - 1886

63
[ 611-73-4 ]
[ 53458-16-5 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 12318 - 12322
Angew. Chem.,2018,vol. 130,p. 12498 - 12502,5

64
[ 5193-03-3 ]
[ 611-73-4 ]
5-chloro-3-phenyl-[1,2,4]triazolo[4,3-a]pyridine [ No CAS ]

Reference： [1]RSC Advances,2018,vol. 8,p. 32597 - 32600
[2]Patent: CN108299426,2018,A .Location in patent: Paragraph 0123-0126

65
[ 13220-33-2 ]
[ 611-73-4 ]
1-methylpyrrolidin-3-yl 2-oxo-2-phenylacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 25℃;Inert atmosphere;	To a stirred solution of N-methyl pyrrol i din- 3-ol (2, 1 equiv) and Et3N (1.2 equiv) in dichloromethane was added a solution of 2- oxo-2- phenyl acetyl chloride (1.1 equiv) in dichloromethane at 0 °C under nitrogen atmosphere for 15 min. The resulting solution was allowed to stir at room temperature over 12h. After completion, the mixture was quenched with water and extracted with diethyl ether to afford the pure product (3B). (0044) Similarly, the product 3B is also obtained by reaction of 2 with other reagents, phenyl oxalic acid, methyl phenyl oxalate, and phenyl hemi-oxaldehyde respectively as shown in Scheme 2.

Reference： [1]Patent: WO2018/154597,2018,A1 .Location in patent: Page/Page column 7; 8

66
[ 22864-65-9 ]
[ 611-73-4 ]
N-(2-benzoyl-4-(trifluoromethyl)phenyl)-N-methylnitrous amide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7737 - 7747

67
[ 22864-65-9 ]
[ 611-73-4 ]
[ 844-87-1 ]

Yield	Reaction Conditions	Operation in experiment
35%		N-methyl-4-trifluoromethylaniline (1d, 0.5mmol, 88mg) and 1,2-dichloride were sequentially added to a 25mL pressure tube.Ethane (2 mL), tert-butyl nitrite (2a, 1.5 mmol, 180 muL), palladium acetate (0.025 mmol, 5.6 mg)And benzoylformic acid (3a, 1 mmol, 150 mg), the pressure-resistant tube was sealed and placed in a reactor, and the reaction was stirred at 40 C for 20 hours.Then, iron powder (2 mmol, 112 mg) and ammonium chloride (1.5 mmol, 80 mg) were directly added to the above reaction system, and reacted at 80 C for 10 hours.After completion of the reaction, it was diluted with a saturated sodium chloride solution (5 mL) and ethyl acetate (8 mL), and then filtered.(5mL × 2) extraction, the organic phase was combined, dried over anhydrous sodium sulfate, distilled solvent under reduced pressure, the residue was purified by silica gel column chromatography(petroleum ether/ethyl acetate = 30/1, v/v),The product was obtained as a yellow oil 4 m (49 mg, 35%).

Reference： [1]Patent: CN109232282,2019,A .Location in patent: Paragraph 0077-0079
[2]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7737 - 7747

68
[ 768-52-5 ]
[ 611-73-4 ]
[ 25082-61-5 ]

Yield	Reaction Conditions	Operation in experiment
55%		<strong>[768-52-5]N-isopropylanilin</strong>e (1h, 0.5mmol, 68mg) and 1,2-dichloroethane were sequentially added to a 25mL pressure tube.(2 mL), tert-butyl nitrite (2a, 1.5 mmol, 180 muL), palladium acetate (0.025 mmol, 5.6 mg)And benzoylformic acid (3a, 1 mmol, 150 mg), the pressure-resistant tube was sealed and placed in a reactor, and the reaction was stirred at 40 C for 20 hours.Then, iron powder (2 mmol, 112 mg) and ammonium chloride (1.5 mmol, 80 mg) were directly added to the above reaction system, and reacted at 80 C for 10 hours.After completion of the reaction, it was diluted with a saturated sodium chloride solution (5 mL) and ethyl acetate (8 mL), and then filtered.(5mL × 2) extraction, the organic phase was combined, dried over anhydrous sodium sulfate, distilled solvent under reduced pressure, the residue was purified by silica gel column chromatography(petroleum ether/ethyl acetate = 30/1, v/v),The yellow solid product 4q (66 mg, 55%).

Reference： [1]Patent: CN109232282,2019,A .Location in patent: Paragraph 0089-0091
[2]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7737 - 7747

69
[ 3119-02-6 ]
[ 611-73-4 ]
C₂₃H₂₂N₂O₃S [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7797 - 7800

70
[ 3119-02-6 ]
[ 611-73-4 ]
N-((4-cyanophenyl)sulfonyl)-2-oxo-2-phenylacetamide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7797 - 7800

71
[ 830-43-3 ]
[ 611-73-4 ]
(E)-5-hexylidene-3-phenyl-1-((4-(trifluoromethyl)phenyl)sulfonyl)-1,5-dihydro-2H-pyrrol-2-one [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7797 - 7800

72
[ 830-43-3 ]
[ 611-73-4 ]
N-((4-(trifluoromethyl)phenyl)sulfonyl)-2-oxo-2-phenylacetamide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7797 - 7800

73
[ 611-73-4 ]
[ 2901-80-6 ]
3-isopropyl-9b-phenyloxazolo[2,3-a]isoindole-2,5(3H,9bH)-dione [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 161 - 172

74
o-(trifluoromethyl)benzenediazonium tetrafluoroborate [ No CAS ]
[ 611-73-4 ]
[ 727-99-1 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 12609 - 12618

75
[ 114046-25-2 ]
[ 611-73-4 ]
4-(1-((4-methoxyphenyl)amino)-2-keto-2-phenylethyl)benzonitrile [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 3711 - 3715

76
[ 4596-92-3 ]
[ 611-73-4 ]
N-(4-chloro-2-formylphenyl)-2-oxo-2-phenylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With triphenylphosphine; copper(I) bromide; In 1,2-dichloro-ethane; at 110℃; for 12.0h;Schlenk technique; Inert atmosphere;	The preparation method is:0.3 mmol of <strong>[4596-92-3]5-<strong>[4596-92-3]chlorobenzo[c]isoxazole</strong></strong> (46 mg), 0.6 mmol benzoylformic acid (90.1 mg), 0.015 mmol of copper bromide (3.3 mg) and 0.06 mmol of triphenylphosphine (15.7 mg) were added to a 25 ml schlenk tube under reduced pressure. The reaction tube was replaced with argon three times. 1,2-dichloroethane (3 ml) was added, and the mixture was stirred at 110 C for 12 hours. At the end of the reaction, 100-200 mesh column chromatography silica gel was added. The solvent was distilled off under reduced pressure, and the crude product was separated by silica gel column chromatography. And eluted with a mixture of petroleum ether and ethyl acetate (petroleum ether: ethyl acetate = 20:1). The TLC elution tracking test is used to collect the eluate containing the target product. Combining the target product eluates, evaporation and concentration gave the ortho-aldehyde group of the alpha-ketoamide compound of the formula III. This material was a yellow solid with a yield of 75%.

Reference： [1]Patent: CN109776488,2019,A .Location in patent: Paragraph 0041; 0042; 0043; 0044; 0045; 0046
[2]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5902 - 5907

77
[ 719-64-2 ]
[ 611-73-4 ]
N-(2-benzoyl-4-chlorophenyl)-2-oxo-2-phenylacetamide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5902 - 5907

78
[ 19012-02-3 ]
[ 611-73-4 ]
1-(4-benzoyl-1-methyl-1H-indol-3-yl)ethanone [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 8102 - 8105

79
[ 698-70-4 ]
[ 611-73-4 ]
N-(4-iodophenyl)-N-methyl-2-oxo-2-phenylacetamide [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4048 - 4054

80
[ 116-02-9 ]
[ 611-73-4 ]
[ 16623-22-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3991 - 3997

81
[ 116-02-9 ]
[ 611-73-4 ]
[ 456-59-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3991 - 3997

82
[ 611-73-4 ]
[ 446065-11-8 ]
[ 4335-77-7 ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 16237 - 16242

83
[ 63-91-2 ]
[ 611-73-4 ]
[ 2566-22-5 ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 15504 - 15507

84
[ 2017-68-7 ]
[ 611-73-4 ]
C₂₀H₁₇NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a mixture of benzoyl formic acid (1.3 mmol) and Et3N (2.3 mmol) in 30 ml of dichloromethane, thionyl chloride (2.3 mmol) was added dropwise with stirring. The reaction was carried out at 0 C in an argon atmosphere for 20 minutes. A solution of beta-naphthylethylamine (1 mmol) in dichloromethane was added dropwise to the reaction mixture at 0C under argon atmosphere. The reaction was completed after stirring at room temperature for 2 days. The reaction progress was monitored by TLC (Sorbfil, 1:3 EtOAc - hexane). The organic layer was washed twice with water and saturated solution NaHCO3. Then the organic layer was again washed with a small amount of water, dried over Na2SO4, the solvent was evaporated, the residue was crystallized from Et2O. The corresponding amide (1 mmol) was dissolved in freshly distilled POCl3 (25 mmol) at 0 C. The reaction was heated at 50 C for 6 days under argon. The progress of reaction was monitored by TLC (Sorbfil, 1:3 EtOAc - hexane). Then the reaction mass was poured on ice, neutralized with 60% KOH solution and extracted with ethyl acetate, the organic layer was dried over Na2SO4. After removing the solvent, the residue was crystallized from Et2O. 3,4-Dihydrobenzo[h]isoquinolin-1-yl(phenyl)methanone (1a). Beige solid, 191 mg (67%), mp 111-113C. 1H NMR (600 MHz, CDCl3) delta (ppm): 8.21 (d, J = 7.6 Hz, 2H), 7.95 (d, J = 8.3 Hz, 1H), 7.86 (d, J = 8.3 Hz, 1H), 7.67 (t, J = 7.3 Hz, 1H), 7.61 (d, J = 8.6 Hz, 1H), 7.56 (t, J = 7.6 Hz, 2H), 7.44-7.41 (m, 2H), 7.33 (t, J = 7.3 Hz, 1H), 3.97 (t, J = 7.3 Hz, 2H), 2.95 (t, J = 7.3 Hz, 2H). 13C NMR (150 MHz, CDCl3) delta (ppm): 193.9, 165.9, 139.3, 135.1, 133.8, 133.2, 132.1, 130.7 (s, 2C), 128.9, 128.7 (s, 2C), 127.1, 126.2, 125.7, 125.4, 124.5, 124.3, 47.0, 27.2. m/z =286 [M + H]+. Anal calcd for C20H15NO (%): C, 84.19; H, 5.30; N, 4.91. Found (%): C, 84.31; H, 5.43; N, 4.89.

Reference： [1]Tetrahedron Letters,2019,vol. 60

85
[ 6344-72-5 ]
[ 611-73-4 ]
C₁₆H₁₂N₂O [ No CAS ]
C₁₆H₁₂N₂O [ No CAS ]

Reference： [1]Journal of Catalysis,2020,vol. 381,p. 38 - 43

86
[ 13708-12-8 ]
[ 611-73-4 ]
C₁₆H₁₂N₂O [ No CAS ]
C₁₆H₁₂N₂O [ No CAS ]

Reference： [1]Journal of Catalysis,2020,vol. 381,p. 38 - 43

87
[ 611-73-4 ]
[ 55687-23-5 ]
3-benzoyl-6-fluoroquinoxalin-2(1H)-one [ No CAS ]

Reference： [1]Advanced synthesis and catalysis,2020

88
[ 2427-71-6 ]
[ 611-73-4 ]
3-benzoyl-6-chloroquinoxalin-2(1H)-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2020,vol. 362,p. 2178 - 2182

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P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 611-73-4 ] {[proInfo.proName]}

Quality Control of [ 611-73-4 ]

Related Doc. of [ 611-73-4 ]

Product Details of [ 611-73-4 ]

Calculated chemistry of [ 611-73-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 611-73-4 ]

Application In Synthesis of [ 611-73-4 ]

[ 611-73-4 ] Synthesis Path-Upstream 1~10

[ 611-73-4 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 611-73-4 ]

Aryls

Ketones

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 611-73-4 ]