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[ CAS No. 99-92-3 ] {[proInfo.proName]}

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Chemical Structure| 99-92-3
Chemical Structure| 99-92-3
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Product Details of [ 99-92-3 ]

CAS No. :99-92-3 MDL No. :MFCD00007896
Formula : C8H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :GPRYKVSEZCQIHD-UHFFFAOYSA-N
M.W : 135.16 Pubchem ID :7468
Synonyms :
p-Aminoacetophenone
Chemical Name :1-(4-Aminophenyl)ethanone

Calculated chemistry of [ 99-92-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.04
TPSA : 43.09 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.28
Log Po/w (XLOGP3) : 0.83
Log Po/w (WLOGP) : 1.48
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 1.44
Consensus Log Po/w : 1.23

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.58
Solubility : 3.56 mg/ml ; 0.0264 mol/l
Class : Very soluble
Log S (Ali) : -1.32
Solubility : 6.51 mg/ml ; 0.0482 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.34
Solubility : 0.615 mg/ml ; 0.00455 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 99-92-3 ]

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 [ 99-92-3 ]

* 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 [ 99-92-3 ]
  • Downstream synthetic route of [ 99-92-3 ]

[ 99-92-3 ] Synthesis Path-Upstream   1~37

  • 1
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Reference: [1] Angewandte Chemie - International Edition, 2007, vol. 46, # 12, p. 2074 - 2077
  • 2
  • [ 154078-59-8 ]
  • [ 19155-24-9 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1995, # 2, p. 337 - 342
  • 3
  • [ 99-92-3 ]
  • [ 95-54-5 ]
  • [ 2963-77-1 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 8, p. 4422 - 4428
  • 4
  • [ 99-92-3 ]
  • [ 334-22-5 ]
  • [ 51639-48-6 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 39, p. 6875 - 6876
  • 5
  • [ 75-15-0 ]
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  • [ 61700-72-9 ]
Reference: [1] Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1976, vol. 283, p. 319 - 321
  • 6
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  • [ 14401-73-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 2014, vol. 72, p. 146 - 159
  • 7
  • [ 99-92-3 ]
  • [ 33720-71-7 ]
Reference: [1] Agricultural and Biological Chemistry, 1984, vol. 48, # 11, p. 2883 - 2888
[2] Arzneimittel-Forschung/Drug Research, 1984, vol. 34, # 11 A, p. 1612 - 1624
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 2016, vol. 59, # 13, p. 546 - 551
  • 8
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  • [ 1788-10-9 ]
YieldReaction ConditionsOperation in experiment
55% With hydrogenchloride; acetic acid; sodium nitrite In water EXAMPLE 24
5-p-Dimethylaminosulphonylphenyl-2-(1-normon-2-yl)oxazole A
The diazonium salt prepared from p-aminoacetophenone (27 g, 0.2 mmol), concentrated hydrochloric acid (140 ml), water (30 ml) and sodium nitrite (14 g, 0.2 mol) was added to a mixture of acetic acid (250 ml), sulphur dioxide (80 g), and cuprous chloride (3 g) at 20° C.
After 40 min the mixture was cooled to 0° C. and water (1 l) added.
Filtration, and drying of the residue followed by recrystallisation from carbon tetrachloride then gave p-acetylbenzenesulphonyl chloride as off-white needles (24 g, 55percent); m.p. 70°-72° C., lit mp=85° C.; δH (CDCl3) 8.1 (4H, S, aryl), 2.6 (3H, S, Me).
Reference: [1] Patent: US4812470, 1989, A,
  • 9
  • [ 99-92-3 ]
  • [ 1788-10-9 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 26, p. 9103 - 9113
[2] Bollettino chimico farmaceutico, 1964, vol. 103, p. 48 - 64
  • 10
  • [ 99-92-3 ]
  • [ 1788-10-9 ]
Reference: [1] Patent: US5859036, 1999, A,
  • 11
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  • [ 124-63-0 ]
  • [ 5317-89-5 ]
YieldReaction ConditionsOperation in experiment
95% at 0 - 20℃; for 2 h; A cooled solution of 4'-aminoacetophenon (10 mmol) in pyridine (10 mL) at 0 °C was treated with METHANESULFONYL chloride (15 mmol) and stirred at room temperature for 2 h. The reaction mixture was diluted with HZ0 and extracted with EtOAc several times. The combined organic layers were washed with H20 and brine, dried over MGS04, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc: hexanes to afford 4'- (Methylsulfonylamino) acetophenone (13-5, LJO-298). 95percent yield, mp = 161 °C 1H NMR (CDC13) 8 7.97 (dd, 2 H, J= 2,6. 8 Hz, ), 7.26 (dd, 2 H, J= 2, 6.8 Hz), 6. 87 (bs, 1 H), 3.10 (s, 3 H), 2.59 (s, 3 H)
66% With pyridine In tetrahydrofuran at 20℃; for 12 h; General procedure: To a solution of 4-aminoacetophenone (0.68g, 5mmol) and pyridine (1.6mL, 20mmol) in THF (10mL) was slowly added the substituted sulfonyl chloride (5mmol). The reaction mixture was stirred at room temperature for 12h. Water (50mL) was added and the mixture was extracted with ethyl acetate (10mL×3), the combined organic phase was washed with 1N hydrochloric acid (30mL×2) and water (30mL×2), dried over anhydrous Na2SO4 and concentrated under vacuum to afford the product.
Reference: [1] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 6, p. 846 - 867
[2] Organic Process Research and Development, 1998, vol. 2, # 2, p. 71 - 77
[3] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 18, p. 6043 - 6053
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2685 - 2688
[5] Patent: WO2005/3084, 2005, A1, . Location in patent: Page 79
[6] Journal of Organic Chemistry, 1987, vol. 52, # 19, p. 4377 - 4379
[7] Journal of Organic Chemistry, 2001, vol. 66, # 25, p. 8293 - 8296
[8] Journal of the American Chemical Society, 2015, vol. 137, # 11, p. 3731 - 3734
[9] Arkivoc, 2016, vol. 2016, # 4, p. 227 - 245
[10] Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1316 - 1318
[11] Chemistry - A European Journal, 2016, vol. 22, # 47, p. 16998 - 17005
[12] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 48 - 65
[13] Journal of medicinal chemistry, 1966, vol. 9, # 1, p. 88 - 97
[14] Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 1982, vol. 38, # 7, p. 791 - 796
[15] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 2, p. 1056 - 1061
[16] Synthesis, 2012, vol. 44, # 9, p. 1329 - 1338
[17] Medicinal Chemistry Research, 2014, vol. 23, # 10, p. 4383 - 4394
[18] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2685 - 2688
  • 12
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  • [ 7143-01-3 ]
  • [ 5317-89-5 ]
Reference: [1] Patent: US2003/153596, 2003, A1,
  • 13
  • [ 937-31-5 ]
  • [ 14235-81-5 ]
  • [ 99-92-3 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 35, p. 4807 - 4810
  • 14
  • [ 110-91-8 ]
  • [ 99-92-3 ]
  • [ 1197-55-3 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2335,2338
[2] Journal of Organic Chemistry, 1946, vol. 11, p. 798,800
  • 15
  • [ 99-92-3 ]
  • [ 14401-72-0 ]
Reference: [1] Journal of Organic Chemistry, 1947, vol. 12, p. 617,680
  • 16
  • [ 99-92-3 ]
  • [ 56759-32-1 ]
YieldReaction ConditionsOperation in experiment
100% With N-Bromosuccinimide In acetonitrile at 20℃; for 20 h; Cooling with ice Example 23 4-acetyl-2-{4-[2-(tetrahydropyran-4-yloxy)ethoxy]phenylamino}benzonitrile (23a) 1-(4-amino-3-bromophenyl)ethanone 1-(4-Aminophenyl)ethanone (10.0 g, 74.0 mmol) was dissolved in acetonitrile (50 mL) and, under ice-cooling, a solution (30 mL) of N-bromosuccinimide (13.8 g, 77.7 mmol) in acetonitrile was added dropwise, and the mixture was stirred at room temperature for 20 hr. The solvent of the reaction mixture was evaporated under reduced pressure, and the obtained residue was dissolved in ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title object compound as a yellow powder (15.8 g, yield 100percent). 1H-NMR (CDCl3, 400 MHz) δ: 2.49 (3H, s), 4.52-4.70 (2H, br), 6.73 (1H, d, J=8.5 Hz), 7.73 (1H, dd, J=8.5, 1.9 Hz), 8.05 (1H, d, J=1.9 Hz).
85% With N-Bromosuccinimide In acetonitrile at 0 - 20℃; To a solution of 4-aminoacetophenone (5.67 g, 0.0419 mol) in 30 mL of CH3CN at 0° C. was added N-bromosuccinimide (7.83 g, 0.0439 mol) in 20 mL of CH3CN dropwise. The reaction was allowed to warm to room temperature and concentrated in vacuo after stirring 16 h. The crude residue was dissolved in EtOAc (100 mL), washed with saturated aqueous NaHCO3 (1.x.100 mL), brine (1.x.100 mL) and dried (Na2SO4). The solvent was removed under vacuum to afford the title compound (7.62 g, 85percent) as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C8H8BrNO, 213.9 (M+H), found 214.0.
71% With N-Bromosuccinimide In toluene at 40℃; for 0.75 h; j00122j Step 1. To a suspension of 1-(4-aminophenyl)-ethanone (14.7 g, 109 mmol) in toluene (150 mL) at 40 °C was added N-bromosuccinimide (19.4 g, 109 mmol) in several portions over 30 mm. After the addition was complete, the mixture was stirred at 40 °C for 15 mm. Water (30 mL) was added and the organic layer was separated, washed with water (3 x 30 mL), dried over magnesium sulfate and evaporated to give the title compound (16.5 g, 77 mmol, 71percent) as a brown crystalline solid. The crude product was used without further purification. LCMS: 97percent, Rt 1.188 mill, ESMS m/z 214 (M+H).
Reference: [1] Patent: US2016/207883, 2016, A1, . Location in patent: Paragraph 0644-0646
[2] Synthetic Communications, 2009, vol. 39, # 2, p. 215 - 219
[3] Chemistry - A European Journal, 2017, vol. 23, # 69, p. 17463 - 17468
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2016, vol. 59, # 13, p. 552 - 556
[5] Agricultural and Biological Chemistry, 1984, vol. 48, # 11, p. 2883 - 2888
[6] Journal of Labelled Compounds and Radiopharmaceuticals, 2016, vol. 59, # 13, p. 546 - 551
[7] Patent: US2007/249649, 2007, A1, . Location in patent: Page/Page column 77-78
[8] Journal of Chemical Research, Synopses, 1995, # 11, p. 457
[9] Patent: WO2015/50471, 2015, A1, . Location in patent: Paragraph 00121; 00122
[10] Patent: US4404222, 1983, A,
[11] Patent: US4407819, 1983, A,
[12] Patent: WO2007/124345, 2007, A2, . Location in patent: Page/Page column 8-9
[13] Chemistry - A European Journal, 2011, vol. 17, # 49, p. 13665 - 13669
[14] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7360 - 7377
[15] Patent: WO2015/20553, 2015, A1, . Location in patent: Paragraph 00128
[16] Patent: WO2015/50472, 2015, A1, . Location in patent: Paragraph 00125; 00126
[17] Journal of the American Chemical Society, 2016, vol. 138, # 40, p. 13147 - 13150
[18] Advanced Synthesis and Catalysis, 2017, vol. 359, # 7, p. 1144 - 1151
[19] Chinese Journal of Chemistry, 2018, vol. 36, # 9, p. 815 - 818
  • 17
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  • [ 107-21-1 ]
  • [ 56759-32-1 ]
Reference: [1] Synthesis, 2007, # 10, p. 1471 - 1474
  • 18
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  • [ 90434-58-5 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5265 - 5270
[2] European Journal of Organic Chemistry, 2014, vol. 2014, # 31, p. 7034 - 7038
  • 19
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  • [ 51529-96-5 ]
Reference: [1] Journal of the Chemical Society, 1930, p. 252,255
  • 20
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  • [ 99-92-3 ]
  • [ 23600-83-1 ]
YieldReaction ConditionsOperation in experiment
53.4% With copper; potassium carbonate In <i>N</i>-methyl-acetamide 368.1
1-(4-anilinophenyl)ethanone
4-amino-acetophenone (4.87 g; 36.0 mmol) is dissolved in dimethylformamide (75 ml).
15 g (0.108 mol) of potassium carbonate (previously dried at 170° C. under an argon atmosphere), 7.236 g (36.0 mmol) of iodobenzene, 0.4 g of copper in powder form and a catalytic quantity of copper iodide are added.
The reaction mixture is taken to reflux for 12 hours.
After leaving the reaction medium to return to ambient temperature, it is filtered on celite and poured into ice-cold water.
After extraction with ethyl acetate, the organic phase is washed with water before being dried over magnesium sulphate, filtered and concentrated under vacuum.
The product obtained is purified by crystallization from heptane in order to produce a yellow solid with a yield of 53.4percent.
Melting point: 105° C.
Reference: [1] Organometallics, 2012, vol. 31, # 21, p. 7336 - 7338
[2] Patent: US2004/132788, 2004, A1,
[3] Patent: US2005/38087, 2005, A1,
  • 21
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  • [ 99-92-3 ]
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YieldReaction ConditionsOperation in experiment
53.4% With potassium carbonate In <i>N</i>-methyl-acetamide 335.1
1-(4-anilinophenyl)ethanone
4-amino-acetophenone (4.87 g; 36.0 mmol) is dissolved in dimethylformamide (75 ml).
15 g (0.108 mol) of potassium carbonate (previously dried at 170° C. under an argon atmosphere), 7.236 g (36.0 mmol) of iodobenzene, 0.4 g of copper powder and a catalytic quantity of copper iodide are added.
The reaction mixture is taken to reflux for 12 hours.
After leaving the reaction medium to return to ambient temperature, the latter is filtered on celite and poured into ice-cooled water.
After extraction with ethyl acetate, the organic phase is washed with water before being dried over magnesium sulphate, filtered and concentrated under vacuum.
The product obtained is purified by crystallization from heptane in order to produce a yellow solid with a yield of 53.4percent.
Melting point: 105° C.
Reference: [1] Patent: US2004/132788, 2004, A1,
[2] Patent: US2005/38087, 2005, A1,
  • 22
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  • [ 108-90-7 ]
  • [ 23600-83-1 ]
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  • 23
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  • [ 23600-83-1 ]
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  • 24
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  • [ 88284-48-4 ]
  • [ 23600-83-1 ]
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  • 25
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  • [ 98-80-6 ]
  • [ 23600-83-1 ]
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  • 26
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  • 27
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  • 28
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  • [ 100-58-3 ]
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  • [ 23600-83-1 ]
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  • 30
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[2] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1959, vol. 17, p. 33,37,41
  • 31
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  • [ 37148-48-4 ]
Reference: [1] Journal of Organic Chemistry, 1947, vol. 12, p. 617,680
  • 32
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  • [ 64-19-7 ]
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  • [ 634-93-5 ]
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  • 33
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  • [ 118727-34-7 ]
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  • 34
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  • [ 149104-90-5 ]
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  • 35
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  • [ 149104-90-5 ]
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  • 36
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  • [ 157014-41-0 ]
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[2] Patent: WO2011/12577, 2011, A1,
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  • [ 343564-14-7 ]
YieldReaction ConditionsOperation in experiment
61% With tris[2-phenylpyridinato-C2,N]iridium(III) In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Irradiation Under nitrogen or argon, 0.4 mmol, 0.2mmol, Ir(ppy) 3(2 mg) was added to the reaction and DMF1 ml flask, and irradiated with a blueLED strip (7W) at room temperature until complete conversion of trivalent iodine reagentcompletion of the reaction. Add 10 ml of saturated Na 2CO 3Aqueous solution, andextracted three times with ethyl acetate, the organic layer was washed with water andonce with saturated brine, dried over anhydrous Na 2SO 4The organic layer was dried.Column chromatography (eluent: petroleum ether 60-90: ethyl acetate = 15: 1-8: 1) to give the product in 61percent yield.
56% With potassium carbonate; nickel(II) hydroxide In dimethyl sulfoxide at 35℃; for 2 h; In the preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is p-aminoacetophenone, and other reactions and post- treatment processes are the same as in the embodiment 28.
The preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is aniline, and the nickel compound is nickel hydroxide.The base is potassium carbonate, and the reaction process parameters are: 1-trifluoromethyl-1,2-phenyliodo-3(H)-one (0.5 mmol, 1.0 eq).Aromatic amine (1.5 mmol, 3.0 eq), nickel hydroxide 10 molpercent, potassium carbonate (1.5 mmol, 3.0 eq),DMSO (2 mL) was reacted at 35 ° C for 2 h, and the other reactions and workup procedures were the same as in Example 1.
Reference: [1] Patent: CN103553857, 2016, B, . Location in patent: Paragraph 0025-0026
[2] Organic Letters, 2014, vol. 16, # 6, p. 1768 - 1771
[3] Organic Letters, 2018, vol. 20, # 13, p. 3732 - 3735
[4] Patent: CN108503552, 2018, A, . Location in patent: Paragraph 0150-0154
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