Name: 874-23-7|2-Acetyl-1-cyclohexanone|98%
Brand: Ambeed
SKU: A109905
Price: 9.0 USD
Availability: InStock
Rating: 93 (28 reviews)

1
[ 874-23-7 ]
[ 141-52-6 ]
[ 506-93-4 ]
[ 58544-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	reagiert analog mit 1-Methyl-3-acetyl-cyclohexanon-⁽²⁾;

Reference： [1]Mitter; Bhattacharya [Journal of the Indian Chemical Society, 1927, vol. 4, p. 156][Chemisches Zentralblatt, 1927, vol. 98, # II, p. 1703]
[2]Mitter; Bhattacharya [Quarterly Journal of the Indian Chemical Society, vol. 4, p. 152,153][Chemisches Zentralblatt, 1927, vol. 98, # II, p. 1703]

2
[ 874-23-7 ]
[ 506-93-4 ]
[ 58544-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate

Reference： [1]Mitter; Bhattacharya [Journal of the Indian Chemical Society, 1927, vol. 4, p. 156][Chemisches Zentralblatt, 1927, vol. 98, # II, p. 1703]

3
[ 874-23-7 ]
[ 14112-98-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With iron(III) trifluoromethanesulfonate; In water; at 80℃; for 12h;	7-Oxooctanoic acid (1d) To a solution of 2-acetylcyclohexanone (1.0 g, 10 mmol) in H2O (10 mL), Fe(OTf)3 (0.25 g, 0.5 mmol) was added. The reaction mixture was vigorously stirred at 80 C for 12 h and the progress of reaction was monitored by TLC. The resulting mixture was warmed to room temperature and extracted with EtOAc (100 mL). The collected organic layer was washed with H2O (100 mL) and brine solution (100 mL).The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification was performed with flash chromatography on silica gel (petroleum ether: diethyl ether 6:4, Rf = 0.3) to afford keto carboxylic acid 1d as a colorless oil. Yield: 0.85 g, 85%; IR (cm-1): 3296 (O-H); 2948 (C-H); 2871 (C-H); 1702 (C=O). 1H NMR (ppm): 1.40-1.32 (m, 2H, CH2); 1.70-1.57 (m, 4H, CH2); 2.16 (s, 3H, CH3); 2.37 (t, 2H, J = 7.5 Hz, CH2); 2.46 (t, 2H, J = 7.4 Hz, CH2). 13C NMR (ppm): 23.4 (CH2); 24.5 (CH2); 28.5 (CH3); 30.0 (CH2); 33.8 (CH2); 43.5 (CH2); 177.4 (C=O); 209.0 (C=O). HRMS (ESI-) m/z calcd for C8H14O3H+ 157.0870, found 157.0874.

Reference： [1]European Journal of Organic Chemistry,2010,p. 2861 - 2866
[2]Chemical Papers,2021,vol. 75,p. 3575 - 3586
[3]Journal of the Chemical Society. Perkin transactions I,1990,p. 1423 - 1427
[4]Journal of Medicinal Chemistry,1983,vol. 26,p. 492 - 499
[5]Advanced Synthesis and Catalysis,2015,vol. 357,p. 4063 - 4068
[6]Journal of the American Chemical Society,1948,vol. 70,p. 4023,4025
[7]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1905,vol. 141,p. 1033
Annales de Chimie (Cachan, France),1912,vol. <8> 26,p. 234
[8]Journal of the American Chemical Society,1963,vol. 85,p. 3752 - 3753
[9]Journal of the American Chemical Society,1988,vol. 110,p. 5203 - 5205
[10]Tetrahedron Asymmetry,1992,vol. 3,p. 1523 - 1524

4
[ 874-23-7 ]
[ 64229-97-6 ]

Yield	Reaction Conditions	Operation in experiment
98%Chromat.	With N-chloro-succinimide; O,O-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) hydrazine-1,2-bis(carbothioate); In methanol; at 25℃; for 0.25h;	General procedure: Fluorous hydrazine-1,2-bis(carbothioate) C1 (0.042 g,0.05 mmol) with NCS (0.013 g, 1.2 mmol) was added inMeOH (3 mL) was stirred at 25 C for 10 min. Thenketone 1 (1 mmol) was added and the resulting mixturewas stirred at 25 C for 1 h. After the reaction completed,the mixture was concentrated and then loaded onto a FluoroFlash silica gel cartridge (5 g), eluted by 80 %methanol at first for non-fluorous components. Then driedover Na2SO4 and evaporated for GC analysis. Ether was then added onto the fluorous gel column to wash out thefluorous hydrazine-1,2-bis(carbothioate) C1. After removalthe ether, compound C1 was dried in vacuo at 40 C for8 h and could be directly used in the next run.

Reference： [1]Tetrahedron,2008,vol. 64,p. 5191 - 5199
[2]Synthesis,2005,p. 1136 - 1140
[3]Synthesis,2011,p. 347 - 351
[4]Chemical Communications,2009,p. 6991 - 6993
[5]Organic Letters,2014,vol. 16,p. 600 - 603
[6]Tetrahedron Letters,2009,vol. 50,p. 473 - 475
[7]Organic and Biomolecular Chemistry,2012,vol. 10,p. 4327 - 4329
[8]Journal of the Chemical Society,1957,p. 4419,4423
[9]Bulletin of the Chemical Society of Japan,1977,vol. 50,p. 1831 - 1835
[10]Catalysis Letters,2016,vol. 146,p. 570 - 574

5
[ 108-94-1 ]
[ 108-24-7 ]
[ 874-23-7 ]

Yield	Reaction Conditions	Operation in experiment
54.4%		Method B. A two-necked heart-shaped flask, equipped with backflow condenser and mechanical stirrer, was charged with cyclohexanone (5.2 mL; 4.9 g; 0.05 mole) and acetic anhydride (9.5 mL); 10.2 g; 0.1 mole). The reaction mixture was chilled and added BF32CH3COOH complex (13.9 mL; 18.8 g; 0.1 mole) at once. The reaction was stirred at room temperature for a period of day. Then, round-bottom flask equipped with backflow condenser and mechanical stirrer was charged with sodium acetate trihydrate (27.2 g; 0.2 mole) and water (150 mL). To the solution obtained, the reaction mixture from heart-shaped flask was transferred, and emulsion was refluxed under vigorous stirring for 3 h. The reaction mixture was further extracted with ether (380 mL). The combined ethereal extract was washed with saturated solution of sodium hydrocarbonate until gas evolution ceased, and dried over magnesium sulphate (MgSO4). Ether was removed and the residue was fractionated under vacuum and nitrogen flow. Fraction having Bp= 105-108C/17 mm Hg was drawn to obtain 2-acetylcyclohexanone (compound 2) yield of 3.8 g (54.4%). 1H- NMR (CDCl3), delta (ppm): 1.69 (4H, m, 4-CH2, 5-CH2); 2.13 (3H, s, 2-COCH3); 2.33 (4H, m, 3-CH2, 6-CH2); 15.8 (1H, s, 2-CH)

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2005,vol. 180,p. 109 - 116
[2]Patent: EP2157088,2010,A1 .Location in patent: Page/Page column 38-39
[3]Journal of the American Chemical Society,1945,vol. 67,p. 284

6
[ 108-94-1 ]
[ 75-36-5 ]
[ 874-23-7 ]

Yield	Reaction Conditions	Operation in experiment
95%		1) 3.4 mL of cyclohexanone was added to 25 mL of re-distilled tetrahydrofuran, cooled to 0-5 C with an ice-water bath, 20 mL of lithium diisopropylamide at a concentration of 2 mol / L was added dropwise,And then remove the ice bath, stirring at room temperature for 1.5h;(2) 9.8 mL of 8 mol / L acetyl chloride in chloroform was added dropwise to the reaction system of step (1) under ice-water bath condition, and then the ice-water bath was removed and stirred for 2 h at room temperature.(3) The product in step (2) was washed twice with water, and then the chloroform in the separated oil phase was spin-dried using a rotary evaporator, and then vacuum distilled under reduced pressure, vacuum degree of vacuum distillation Was -0.960 MPa, the fraction of 118-136 C was collected in 3.2 mL, and the resulting fraction was 2-acetylcyclohexanone in a yield of 95%.

Reference： [1]Patent: CN106083554,2016,A .Location in patent: Paragraph 0009; 0024-0027
[2]Journal of the Chemical Society,1957,p. 1718,1725
[3]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1951,vol. 233,p. 876
[4]Synthetic Communications,1996,vol. 26,p. 2901 - 2904

7
[ 874-23-7 ]
[ 23645-69-4 ]

Yield	Reaction Conditions	Operation in experiment
52%	With ammonium acetate; In benzene;Reflux; Dean-Stark;	IR spectra were recorded on an FT-801 FTIR spectrometer in HCl3 (compounds 2a-c) and in KBr pellets (the rest of the compounds). 1H and 13C NMR spectra were acquired on a Bruker DRX-400 spectrometer (400 and 100 MHz, respectively). The internal standard was TMS. Elemental analysis was performed on a Carlo Erba 1106 CHN elemental analyzer. Melting points were determined on a Kofler bench. The reaction progress and the purity of the obtained compounds was controlled by TLC on Sorbfil AF-A-UV plates. The enamino ketones 1a- were obtained by heating benzene solutions of the 1,3-dicarbonyl compounds 6- with ammonium acetate, while using a flask with a Dean-Stark trap [13]. The yield of compound 1a was 78%, compound 1b - 43%, compound 1c - 52%. The IR and NMR spectra of compounds 2, 4, 5 fully matched those of the previously described compounds [10, 12].

Reference： [1]Chemistry of Heterocyclic Compounds,2014,vol. 50,p. 217 - 224
[2]Chemistry of Heterocyclic Compounds,2014,vol. 50,p. 217 - 224
Khim. Geterotsikl. Soedin.,2014,vol. 50,p. 241 - 249,9
[3]Journal of Organic Chemistry,1970,vol. 35,p. 1632 - 1641

8
[ 874-23-7 ]
[ 3580-37-8 ]

Yield	Reaction Conditions	Operation in experiment
74%	With hydrogenchloride; SULFAMIDE In methanol for 1h; Ambient temperature;
	With hydrogenchloride; SULFAMIDE In ethanol

Reference： [1]Castro, Ana; Martinez, Ana [Journal of the Chemical Society. Perkin transactions II, 1994, # 7, p. 1561 - 1564]
[2]Wright,J.B. [Journal of Organic Chemistry, 1964, vol. 29, p. 1905 - 1909]

9
[ 874-23-7 ]
[ 74-89-5 ]
[ 4492-50-6 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1966,p. 1732 - 1735
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1966,p. 1795 - 1799

10
[ 874-23-7 ]
[ 74-88-4 ]
[ 1195-75-1 ]

Yield	Reaction Conditions	Operation in experiment
74.7%	With sodium hydroxide; In methanol; water; at 20℃;Cooling with ice; Reflux;	Example 3. Preparation of 2-acetyl-2-methylcyclohexanone (compound 3) A three-necked round-bottom flask equipped with backflow condenser, mechanical stirrer, and thermometer, on cooling with ice, was charged with methyl alcohol (83 mL), <strong>[874-23-7]2-acetylcyclohexanone</strong> (compound 2) (29.0 g; 26.9 mL; 0.21 mole), and methyl iodide (44.0 g; 19.3 mL; 0.31 mole). Under stirring, the solution of sodium hydroxide (8.27 g, 0.21 mole) in water (41.4 mL) was added dropwise to the reaction mixture. The reaction was stirred at room temperature for 20 h and, then, refluxed for 2 h. After chilling, the reaction mixture was transferred to a separating funnel, water (85 mL) was added, and the mixture was extracted with chloroform (2*85 mL). Combined chloroform extracts were washed with 2M sodium hydroxide (200 mL), saturated solution of sodium chloride (100 mL), and dried over MgSO4. The solvent was removed and the residue was fractionated under vacuum and nitrogen flow. Fraction having Bp= 123-128C/32 mm Hg was drawn to obtain 2-acetyl-2-methylcyclohexanone (compound 3) yield of 23.8 g (74.7%). 1H- NMR (CDCl3), delta (ppm): 1.23 (3H, s, 2-CH3); 1.41-1.48 (1H, m, 4-CH2); 1.61-1.69 (3H, m, 4-CH2, 5-CH2); 1.93-1.99 (1H, m, 3-CH2); 2.09 (3H, s, 2-COCH3); 2.25-2.34 (1H, m, 3-CH2); 2.42-2.48 (2H, m, 6-CH2)

Reference： [1]Russian Chemical Bulletin,2008,vol. 57,p. 608 - 611
[2]Patent: EP2157088,2010,A1 .Location in patent: Page/Page column 39
[3]Synthesis,1977,p. 113 - 116

11
[ 75-77-4 ]
[ 874-23-7 ]
[ 62269-46-9 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 1395 - 1402
[2]Synlett,2000,p. 497 - 500
[3]Tetrahedron,1982,vol. 38,p. 1413 - 1416
[4]Tetrahedron Letters,1999,vol. 40,p. 985 - 988
[5]Chemistry - A European Journal,2000,vol. 6,p. 3204 - 3214

12
[ 7357-70-2 ]
[ 874-23-7 ]
[ 95546-96-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine In ethanol at 40 - 45℃; for 4h;
78%	With piperidine In ethanol for 4h; Heating;

Reference： [1]Sharanin, Yu. A.; Shestopalov, A. M.; Promonenkov, V. K.; Rodinovskaya, L. A. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 2216 - 2224][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 11, p. 2432 - 2441]
[2]Al-Omran, Fatima; Elassar, Abdel-Zaher A; El-Khair, Adel A [Tetrahedron, 2001, vol. 57, # 51, p. 10163 - 10170]

13
[ 6829-40-9 ]
[ 874-23-7 ]
[ 37945-37-2 ]
ethyl 3-methyl-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3986 - 3993

14
[ 6829-41-0 ]
[ 874-23-7 ]
[ 37945-37-2 ]
ethyl 3-methyl-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3986 - 3993

15
[ 874-23-7 ]
[ 74279-75-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With 1-methyl-3-(propyl-3-sulfonyl)imidazolium trifluoromethanesulfonate; 1-butyl-3-ethylimidazolium hexafluorophosphate; Selectfluor; at 80℃; for 7h;Inert atmosphere; Schlenk technique;	General procedure: The carbonyl compound (0.25mmol) and Selectfluor (0.25mmol) were added to [BMIM][PF6] (25equiv) in a Schlenk tube, and [PMIM(SO3H)][OTf] (?0.5mmol) was introduced at rt with stirring under a nitrogen atmosphere. The reaction mixture was stirred at 80C for the specified period of time (see Tables). After completion of the reaction (TLC monitoring), the reaction mixture was extracted several times with diethyl ether (4×10mL), and the combined organic extracts were washed with aqueous saturated NaHCO3 followed by water, dried (MgSO4), and the solvent was evaporated under vacuum. The crude product was purified by silica gel column chromatography using 3-6% diethyl ether in hexane as eluent.

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 3379 - 3385
[2]Tetrahedron Letters,2007,vol. 48,p. 2671 - 2673
[3]Tetrahedron Letters,2015,vol. 56,p. 5495 - 5499
[4]European Journal of Organic Chemistry,2015,vol. 2015,p. 3779 - 3786
[5]Tetrahedron Letters,1980,vol. 21,p. 277 - 280
[6]Journal of Organic Chemistry,1995,vol. 60,p. 6563 - 6570
[7]Journal of Fluorine Chemistry,2003,vol. 120,p. 173 - 183

16
[ 874-23-7 ]
[ 137-07-5 ]
[ 120-75-2 ]
[ 78840-22-9 ]
2-methyl-2-(5-benzothiazol-2-ylpentyl)-2,3-dihydrobenzothiazole [ No CAS ]
[ 182-53-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 26% 2: 23.5% 3: 20% 4: 33%	With toluene-4-sulfonic acid In toluene for 10h; Heating;

Reference： [1]Trapani, Giuseppe; Reho, Antonia; Latrofa, Andrea; Morlacchi, Flaviano; Liso, Gaetano [Journal of Chemical Research, Miniprint, 1986, # 3, p. 954 - 976]

17
[ 874-23-7 ]
[ 107-91-5 ]
[ 17012-30-5 ]

Yield	Reaction Conditions	Operation in experiment
59.6%	With piperidine; In ethanol; at 70℃; for 12h;	Example 1:1 -Methyl-3-oxo-2,3,5,6,7,8-hexahydroisoqu inol ine-4-carbonitri leTo a solution of <strong>[874-23-7]2-acetylcyclohexanone</strong> (20 g, 143 mmol) in 150 mL of ethanol were added 2-cyanoacetamide (12.00 g, 143 mmol) and piperidine (70.6mL, 713 mmol) and the reaction mixture was heated for 12 h at 70 C. After the reaction was complete, the reaction mixture was cooled to room temperature and filtered, followed by an ethanol wash to obtain the title compound.Yield: 16 g (59.6 %); 1H NMR (DMSO-d6, 300 MHz): 6 12.11 (5, 1H), 2.71 (5, 2H), 2.36 (5, 2H), 2.20 (5, 3H) 1.66 (br 5, 4H); MS (ES 1+) m/z 189.1 (M+H).
	In ethanol;	(1) 4-Cyano-2,3,5,6,7,8-hexahydro-1-methyl-3-oxoisoquinoline <strong>[874-23-7]2-Acetylcyclohexanone</strong> (5 g) and cyanoacetamide (3 g) were added to 25 ml of ethanol and a small amount of piperidine was also added. The mixture was heated under reflux for 2 hours. After cooling, deposited crystals were filtered out and washed with ethanol. There was obtained 4.5 g of 4-cyano-2,3,5,6,7,8-hexahydro-1-methyl-3-oxoisoquinoline. mp: 271 C. (decomposition). NMR deltaTMSCF3COOH: 1.8-2.1 (4H, m); 2.56 (3H, s); 2.6-3.2 (4H, m).
	With 1,4-diaza-bicyclo[2.2.2]octane; In ethanol; at 90℃; for 8h;	The <strong>[874-23-7]2-acetyl cyclohexanone</strong> (1.4g, 10mmol), Cyanothioacetamide (8.4g, 10mmol) and three ethylene diamidogen six hydrate (2.2g, 10mmol) is added to the anhydrous alcohol, 90 C stirring 8h, cessation of the reaction, is dropped to the room temperature, the precipitate filtered, and ethanol or methanol or ethyl acetate for recrystallization.

Reference： [1]Patent: WO2015/110999,2015,A1 .Location in patent: Page/Page column 58
[2]Journal of Medicinal Chemistry,1989,vol. 32,p. 351 - 357
[3]Patent: US4639521,1987,A
[4]RSC Advances,2015,vol. 5,p. 25967 - 25978
[5]Patent: CN105037360,2016,B .Location in patent: Paragraph 0230; 0231; 0232

18
[ 72179-84-1 ]
[ 874-23-7 ]
1,4-dimethyl-5,6,7,8-tetrahydro-1H-2,1,3-benzothiadiazine 2,2-dioxide [ No CAS ]
3,4-dimethyl-5,6,7,8-tetrahydro-3H-2,1,3-benzothiadiazine 2,2-dioxide [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1994,p. 1561 - 1564

19
[ 670-80-4 ]
[ 75-36-5 ]
[ 874-23-7 ]

Yield	Reaction Conditions	Operation in experiment
72%		To a 0.65 M solution of 4-cyclohex-l-enyl-morpholine (82.64 g, 0.50 mol, 1 eq.), obtained in Example 1, in toluene (770 ml) is added triethylamine (71.33 g, 0.70 mol, 1.41 eq). Acetyl chloride (55.34 g, 0.70 mol, 1.41 eq)) is then added dropwise and the reaction mixture is further stirred at 350C for 20 hours and then at room temperature overnight.After completion of the reaction (followed by GC), a 20% HCl aqueous solution (250 mL) is added and the mixture is stirred under reflux for 1 hour.After cooling down, the organic phase is washed twice with water, once with saturated aqueous NaHCO3 solution and with brine. The organic phase is then dried over magnesium sulphate and the solvents are evaporated. The crude oil is then purified by distillation to give compound IVa as a colourless oil (49.95 g, 0.36 mol, 72% yield).Bp: 48C / 0.6 torr
55%		Method A. A three-necked flask equipped with backflow condenser, mechanical stirrer, thermometer, and dropping funnel was charged with anhydrous chloroform (475 mL), 1-morpholinocyclohexene (compound 1) (63.0 g; 0.38 mole), and triethylamine (56.7 mL; 41.28 g; 0.41 mole) rectified over sodium. To the reaction mixture chilled to 0C, the solution of acetyl chloride (27.7 mL; 30.61 g; 0.39 mole) in anhydrous chloroform (140 mL) was added dropwise at such a rate to maintain the reaction temperature not higher than 0C. The reaction mixture was further stirred on cooling with ice for 1 h, then, it was kept at room temperature for 12 h. Next, the reaction mixture was transferred to round-bottom flask equipped with backflow condenser and mechanical stirrer, the solution of concentrated hydrochloric acid (50.4 mL) in water (126 mL) was added thereto, and the reaction was refluxed under continuous stirring for 5 h. After chilling, the chloroform layer was separated, washed with water portions by 200 mL (up to pH 5-6), saturated solution of sodium chloride, and dried over sodium sulphate. Chloroform was removed and the residue was fractionated under vacuum. Fraction having Bp= 102-104C/10 mm Hg was drawn to obtain 2-acetylcyclohexanone (compound 2) yield of 29.0 g (55%). 1H- NMR (CDCl3), delta (ppm): 1.67 (4H, m, 4-CH2, 5-CH2); 2.1 (3H, s, COCH3); 2.31 (4H, m, 3-CH2, 6-CH2); 15.9 (1H, s, 2-CH)

Reference： [1]Patent: WO2011/13077,2011,A1 .Location in patent: Page/Page column 10
[2]Patent: EP2157088,2010,A1 .Location in patent: Page/Page column 38
[3]Bulletin de la Societe Chimique de France,1970,p. 2678 - 2685

20
[ 3775-29-9 ]
[ 874-23-7 ]
4-Methylene-spiro[5.5]undecane-1,7-dione [ No CAS ]
1-Acetyl-3-methylene-bicyclo[3.3.1]nonan-9-one [ No CAS ]
Acetic acid 2-(1-acetyl-2-oxo-cyclohexylmethyl)-allyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 13% 2: 10% 3: 16%	With triphenylphosphine In acetonitrile at 40℃; for 6h;

Reference： [1]Buono, Frédéric; Tenaglia, Alphonse [Synlett, 1998, # 10, p. 1153 - 1155]

21
[ 874-23-7 ]
[ 106675-70-1 ]
3-hydroxy-5-(2-oxo-cyclohexylidene)-5H-furan-2-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,1999,vol. 38,p. 1803 - 1805

22
[ 874-23-7 ]
[ 106675-70-1 ]
3-hydroxy-5-(2-oxo-cyclohexylidene)-5H-furan-2-one [ No CAS ]
7-acetyl-3-hydroxy-5,6-dihydro-4H-benzofuran-2-one [ No CAS ]

Reference： [1]Chemistry - A European Journal,2000,vol. 6,p. 3204 - 3214

23
[ 874-23-7 ]
[ 17339-96-7 ]

Yield	Reaction Conditions	Operation in experiment
30%	With (Z/E)-2-bromo-2-[4-oxothiazolidin-2-ylidene]-N-phenylacetamide; dimethyl sulfoxide; for 7.5h;Reflux;	General procedure: A mixture of a substrate (0.6 mmol), vinyl bromide 2a (0.06 mmol) in DMSO (1.1 mL) was heated in an open flask (the temperature of an oil bath and the reaction time are specified in refPreviewPlaceHolderTable 2). After the completion of the reaction (checked by TLC), the reaction mixture was diluted with water (11 mL), saturated with NaCl and extracted with ethyl acetate (5×4 mL). Only in the case of the synthesis of arylglyoxals the organic layer was additionally washed with Na2CO3 (0.12 mmol in 2 mL of water), with saturated aq NaCl and dried with anhydrous Na2SO4. Column chromatography (eluent: gradient petrolether/ethyl acetate) of the extract gave the pure products.

Reference： [1]European Journal of Organic Chemistry,2010,p. 7020 - 7026
[2]Journal of Organic Chemistry,2013,vol. 78,p. 11584 - 11589
[3]Chemistry - A European Journal,2009,vol. 15,p. 10713 - 10717
[4]Angewandte Chemie - International Edition,2014,vol. 53,p. 548 - 552
Angew. Chem.,2014,vol. 53,p. 558 - 562,5
[5]Synlett,2002,p. 119 - 121
[6]European Journal of Organic Chemistry,2003,p. 425 - 431
[7]Tetrahedron,2011,vol. 67,p. 8000 - 8008

24
[ 874-23-7 ]
[ 28329-46-6 ]

Reference： [1]Russian Chemical Bulletin,2009,vol. 58,p. 392 - 394
[2]Synlett,2003,p. 493 - 496

25
[ 2497-18-9 ]
[ 874-23-7 ]
(S)-2-acetyl-2-[(E)-2-hexenyl]cyclohexanone [ No CAS ]
(R)-2-acetyl-2-[(E)-2-hexenyl]cyclohexanone [ No CAS ]

Reference： [1]Organic Letters,2003,vol. 5,p. 2177 - 2179

26
[ 874-23-7 ]
[ 67-63-0 ]
hexanedioic acid isopropyl ester [ No CAS ]
[ 6938-94-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 43% 2: 40%	With potassium peroxomonosulfate at 20℃; for 18h;

Reference： [1]Yan, Jun; Travis, Benjamin R.; Borhan, Babak [Journal of Organic Chemistry, 2004, vol. 69, # 26, p. 9299 - 9302]

27
[ 874-23-7 ]
[ 536-74-3 ]
2-(1-oxoethyl)-2-(1-phenylethenyl)cyclohexanone [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 4823 - 4825
[2]Journal of the American Chemical Society,2007,vol. 129,p. 5264 - 5271
[3]European Journal of Organic Chemistry,2019,vol. 2019,p. 4101 - 4104
[4]Journal of Organometallic Chemistry,2012,vol. 716,p. 6 - 10

28
[ 673-32-5 ]
[ 874-23-7 ]
2-trans-cinnamyl-2-acetylcyclohexanone [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2006,p. 4211 - 4213
[2]Journal of Organic Chemistry,2004,vol. 69,p. 6478 - 6481
[3]Green Chemistry,2017,vol. 19,p. 1861 - 1865

29
[ 874-23-7 ]
[ 536-74-3 ]
4-acetyl-3-phenyl-cyclooct-3-enone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 11368 - 11369

30
[ 874-23-7 ]
[ 1817-49-8 ]
2-acetyl-2-(1,3-diphenyl-2-propynyl)cyclohexanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With bismuth (III) nitrate pentahydrate; 3-butyl-1-ethyl-4-nitroimidazolium bis(trifluoromethylsulfonyl)imide; at 20 - 40℃; for 3.16667h;Inert atmosphere;	General procedure: The desired ionic liquid (2 mL if the reactants were liquids and 3.00-3.5 mL for solids) was charged into an oven-dried Schlenk tube under a nitrogen atmosphere, The Lewis acid (10 mol%) was then introduced and was dissolved or immobilized in the IL upon sonication (for about 15 min). No catalyst was used in entries 1 and 9 in Table 1. The respective 1,3-diketone or the 4-hydroxycoumarin was then introduced into the Schlenk tube under a nitrogen atmosphere followed by the desired propargylic alcohol. The reaction mixture was magnetically stirred, initially at r. t. for about 10 minutes followed by stirring in a pre-heated oil bath at 30 to 60 C (as specified; refer to Tables 1-3), until completion (monitored by TLC). Once the reaction was over, the contents were cooled to r. t. and extracted with dry diethyl ether or with EtOAc-Hexane (2:3 vol/vol), until the final extraction did not show a spot corresponding to the starting material or to the product). The combined organic extracts were washed with DI water, dried with MgSO4 and concentrated to give the crude product, which upon purification through column chromatography furnished the desired products. In some cases the crude reaction mixture obtained upon evaporation of the combined organic extracts was directly charged onto a column for purification without a water wash.

Reference： [1]Synthetic Communications,2011,vol. 41,p. 243 - 254
[2]Chemistry Letters,2008,vol. 37,p. 878 - 879
[3]Tetrahedron Letters,2011,vol. 52,p. 6859 - 6864
[4]Organic Letters,2007,vol. 9,p. 727 - 730

31
[ 35466-83-2 ]
[ 874-23-7 ]
[ 67679-11-2 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 3288 - 3290
[2]Advanced Synthesis and Catalysis,2013,vol. 355,p. 973 - 980

32
[ 874-23-7 ]
[ 104-21-2 ]
2-acetyl-2-[(4-methoxyphenyl)methyl]cyclohexanone [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 6109 - 6112

33
[ 874-23-7 ]
[ 88267-97-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: conc. HCl / ethanol / 4 h / Heating 2: 10percent NaOH / H₂O / 8 h / Heating

Reference： [1]Sekiya; Hiranuma; Kanayama; Hata; Yamada [Chemical and pharmaceutical bulletin, 1983, vol. 31, # 7, p. 2254 - 2261]

34
[ 874-23-7 ]
[ 83939-60-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: conc. HCl / ethanol / 4 h / Heating 2: 10percent NaOH / H₂O / 8 h / Heating 3: 52 percent / POCl₃ / 4 h / Heating

Reference： [1]Sekiya; Hiranuma; Kanayama; Hata; Yamada [Chemical and pharmaceutical bulletin, 1983, vol. 31, # 7, p. 2254 - 2261]

35
[ 27277-03-8 ]
[ 874-23-7 ]
[ 623931-72-6 ]

Yield	Reaction Conditions	Operation in experiment
49%	In 2-methoxy-ethanol for 18h; Heating / reflux;	25.1 Example 25 Preparation of (5R, 6Z)-6-r [(5-methyl-6,7,8,9-tetrahydro[1,2,4]triazolo[1,5- alquinazolin-2-yl) methylenel-7-oxo-4-thia-1-azabicyclo [3. 2. Olhept-2-ene-2- carboxylic acid, sodium salt Step 1: Preparation of (5-Methvl-6, 7, 8, 9-tetrahYdro-r1, 2, 41triazolor1, 5- a]quinazolin-2-yl)-methanol : To a round bottomed flask was loaded 4.2 grams of 2-acetylcyclohexanone, 3.52 grams of (5-Amino-1H-[1, 2,4] triazol-3-yl)-methanol and 50ml 2-methoxyethanol. The mixture was refluxed for 18 hours. Then it was cooled down to 23°C and concentrated to 5mi. Then 50moi ethyl ether was added and the precipitate was filtered and vacuum dried to yielded 3.32 grams of product Yield. 49%. This compound was used directly for the next step. MS: 219.2 (M+H). H-NMR (DMSO): 6 5.49 (t, 1 H, OH, J= 6Hz), 4.61 (d, 2H, J= 6Hz), 3.24 (m, 2H), 2.93 (m, 2H), 2.69 (s, 3H), 2.52 (s, 2H), 1.84 (m, 4H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2003/93280, 2003, A1 Location in patent: Page/Page column 146

36
[ 129946-63-0 ]
[ 874-23-7 ]
[ 129946-36-7 ]

Yield	Reaction Conditions	Operation in experiment
	In ice-water; acetic acid;	STR59 5.2 ml (0.04 mol) of 2-acetylcyclohexanone (cf., for example, J. org. Chem. 34, 1425-1429 [1969]) are added to 6.76 g (0.04 mol) of <strong>[129946-63-0]4-cyano-2,5-difluorophenylhydrazine</strong> in 40 ml of glacial acetic acid, the reaction mixture is stirred at room temperature for 2 hours and then stirred into 250 ml of ice-water, the mixture is extracted with dichloromethane, dried over sodium sulphate and evaporated in vacuo, and the residue is recrystallized from dichloromethane/n-hexane. 3.21 g (23.5% of theory) of 4-(5-methyl-3,4-tetramethylene -1-pyrazolyl)-2,5-difluorobenzonitrile of melting point 120 C. are obtained.
	In ice-water; acetic acid;	Example 2 (Process a) 5.2 ml (0.04 mol) of 2-acetylcyclohexanone (cf., for example, J. org. Chem. 34, 1425-1429 [1969]) are added to 6.76 g (0.04 mol) of <strong>[129946-63-0]4-cyano-2,5-difluorophenylhydrazine</strong> in 40 ml of glacial acetic acid, the reaction mixture is stirred at room temperature for 2 hours and then stirred into 250 ml of ice-water, the mixture is extracted with dichloromethane, dried over sodium sulphate and evaporated in vacuo, and the residue is recrystallized from dichloromethane/n-hexane. 3.21 g (23.5% of theory) of 4-(5-methyl-3,4-tetramethylene-1-pyrazolyl)-2,5-difluorobenzonitrile of melting point 120 C. are obtained.

Reference： [1]Patent: US5006148,1991,A
[2]Patent: US6906006,2005,B1

37
[ 27277-03-8 ]
[ 60-29-7 ]
[ 874-23-7 ]
[ 623931-72-6 ]

Yield	Reaction Conditions	Operation in experiment
49%	In 2-methoxy-ethanol at 23℃; for 18h; Heating / reflux;	25.1 STEP 1: PREPARATION OF (5-METHYL-6,7,8,9-TETRAHYDRO-[1,2,4]TRIAZOLO[1,5-A]QUINAZOLIN-2-YL)-METHANOL To a round bottomed flask was loaded 4.2 grams of 2-acetylcyclohexanone, 3.52 grams of (5-Amino-1H-[1,2,4]triazol-3-yl)-methanol and 50 ml 2-methoxyethanol. The mixture was refluxed for 18 hours. Then it was cooled down to 23° C. and concentrated to 5 ml. Then 50 ml ethyl ether was added and the precipitate was filtered and vacuum dried to yielded 3.32 grams of product Yield. 49%. This compound was used directly for the next step. MS: 219.2(M+H). H-NMR(DMSO): δ 5.49(t, 1H, OH, J=6 Hz), 4.61(d, 2H, J=6 Hz), 3.24 (m, 2H), 2.93 (m, 2H), 2.69 (s, 3H), 2.52 (s, 2H), 1.84 (m, 4H).
	In 2-methoxy-ethanol	68.1 Step 1 Step 1 Preparation of (5-Methyl-6,7,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]quinazolin-2-yl)-methanol: To a round bottomed flask was loaded 4.2 grams of 2-acetylcyclohexanone, 3.52 grams of (5-Amino-1H-[1,2,4]triazol-3-yl)-methanol and 50 ml 2-methoxyethanol. The mixture was refluxed for 18 hours. Then it was cooled down to 23° C. and concentrated to 5 ml. Then 50 ml ethyl ether was added and the precipitate was filtered and vacuum dried to yielded 3.32 grams of product Yield. 49%. This compound was used directly for the next step. MS: 219.2(M+H). H-NMR(DMSO): δ 5.49(t, 1H, OH, J=6 Hz), 4.61(d, 2H, J=6 Hz), 3.24 (m, 2H), 2.93 (m, 2H), 2.69 (s, 3H), 2.52 (s, 2H), 1.84 (m, 4H).

Reference： [1]Current Patent Assignee: PFIZER INC - US2006/276446, 2006, A1 Location in patent: Page/Page column 27
[2]Current Patent Assignee: PFIZER INC - US2004/132708, 2004, A1

38
[ 874-23-7 ]
[ 14527-26-5 ]
[ 124956-61-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide;	a: 5,6,7,8-Tetrahydro-4-methyl-2-methyl-thioquinazoline 14 g (0.1 mole) of 2-acetylcyclohexanone was added to 120 ml of methanolic solution containing 11.2 g (0.2 mole) of potassium hydroxide at room temperature while stirring. 27.8 g (0.1 mole) of 2-methyl-2-thiopseudourea sulfate was then added to the mixture and the stirring was continued for 18 hours. The reaction mixture was then poured into ice-water, and the mixture was made acidic with acetic acid. The oil which separated was collected by decantation and triturated with ice water to give 5 g of 5,6,7,8-tetrahydro-4-methyl-2-methylthioquinazoline, m.p. 38-40C. The product was recrystallized from iPr0H-H20, m.p. 43-44C; MS (EI): m/e 194 (M+). 200 MHz NMR (CDCl3) w: 1.80 (4H, m), 2.34 (3H, s), 2.52 (3H, s), 2.57 (2H, m), 2.76 (2H, s).

Reference： [1]Patent: EP324520,1990,A3

39
[ 874-23-7 ]
[ 123-54-6 ]
[ 14112-98-2 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 7793 - 7795

40
[ 874-23-7 ]
[ 20504-00-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,10-(ethane-1,2-diyl)phenanthrolinediium bistribromide; In ethyl acetate; at 5 - 10℃; for 0.316667h;	11. Preparation of 2-acetyl-2-bromocyclohexanone (11b): 0.6 mmol of EPDTB (0.818 g) and 1 mmolof <strong>[874-23-7]2-acetylcyclohexanone</strong> (0.130 mL) were dissolved in 5 mL of EtOAc. The resultant mixture wasstirred maintaining cool condition (5-10oC) in a magnetic stirrer for ca. 19 min until the solution becomescolourless. The progress of the reaction was monitored by doing TLC (10 % EtOAc/hexane). After thecompletion of reaction, the mixture was washed with water (2 X 5 mL). The organic layer was dried overanhyd Na2SO4 after separating from aq layer. The excess solvent was removed by evaporation in a rotaryevaporator to get the crude liquid product.

Reference： [1]Tetrahedron,2008,vol. 64,p. 5191 - 5199
[2]Tetrahedron Letters,2009,vol. 50,p. 473 - 475
[3]Organic Letters,2014,vol. 16,p. 600 - 603
[4]Synthetic Communications,2015,vol. 45,p. 724 - 736
[5]Organic Letters,2018,vol. 20,p. 1875 - 1879

41
[ 874-23-7 ]
[ 60-12-8 ]
[ 1234705-17-9 ]
[ 103-45-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 85% 2: 11%	With indium(III) triflate at 80℃; for 24h; Neat (no solvent); Inert atmosphere;

Reference： [1]Location in patent: experimental part Kuninobu, Yoichiro; Kawata, Atsushi; Noborio, Taihei; Yamamoto, Syun-Ichi; Matsuki, Takashi; Takata, Kazumi; Takai, Kazuhiko [Chemistry - An Asian Journal, 2010, vol. 5, # 4, p. 941 - 945]

42
[ 64-17-5 ]
[ 874-23-7 ]
[ 36651-36-2 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 2861 - 2866

43
[ 874-23-7 ]
[ 1019208-03-7 ]
(1SR,5RS)-1-acetyl-3-benzyl-3-azabicyclo[3.3.1]nonan-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With Methyltrichlorosilane; In dichloromethane; at 0 - 20℃;	General procedure: Method A: To a solution of the ketone (1.0 equiv) and the 3-alkyl-1,5,3-dioxazepane (1.2 equiv) in dry CH2Cl2 (2 mL/mmol) was added MeSiCl3 (1.2 equiv). The reaction mixture was stirred until the consumption of the ketone was observed by thin-layer chromatography (3:1 hexane/ethyl acetate). The reaction was quenched with 2 M HCl and diluted with Et2O. The organic layer was extracted with 2 M HCl and the combined aqueous extracts were basified with solid NaHCO3. The resulting mixture was extracted with Et2O, dried over MgSO4, concentrated in vacuo, and if necessary, purified by flash column chromatography, using the solvent system stated, to afford the title compounds.Method B: To a solution of the ketone (1.0 equiv) and the 3-alkyl-1,5,3-dioxazepane (1.3 equiv) in dry CH2Cl2 (10 mL/mmol) was added distilled TiCl4 (0.5 equiv) dropwise at 0 C. The reaction mixture was stirred until the consumption of the ketone was observed by thin-layer chromatography (3:1 hexane/ethyl acetate). The reaction was quenched with satd NaHCO3, extracted with CH2Cl2 (using a centrifuge at 3000 rpm for 5 min). The combined organic extracts were dried over MgSO4, concentrated in vacuo and purified by flash chromatography on silica gel, using the solvent system stated, to afford the title compounds.Method C: To a solution of the 3-alkyl-1,5,3-dioxazepane (1.2 equiv) in dry CH2Cl2 (circa 2 mL/mmol) was added CH3SiCl3 (1.2 equiv). The reaction mixture was stirred for 30 min followed by addition of the ketone (1.0 equiv). The reaction mixture was then stirred until the consumption of the ketone was observed by thin-layer chromatography (3:1 hexane/ethyl acetate). The reaction was quenched with 2 M HCl and diluted with Et2O. The organic layer was extracted with 2 M HCl and the combined aqueous extracts were basified with solid NaHCO3. The resulting mixture was extracted with Et2O, dried over MgSO4, concentrated in vacuo, and if necessary, purified by flash chromatography on silica gel, using the solvent system stated, to afford the title compounds.

Reference： [1]Tetrahedron,2012,vol. 68,p. 1017 - 1028

44
[ 7357-70-2 ]
[ 874-23-7 ]
[ 95546-96-6 ]
4-methyl-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In ethanol at 20℃; regioselective reaction;

Reference： [1]Location in patent: experimental part Dotsenko; Krivokolysko; Polovinko; Litvinov [Chemistry of Heterocyclic Compounds, 2012, vol. 48, # 2, p. 309 - 319]

45
[ 874-23-7 ]
[ 18061-10-4 ]
[ 1414632-61-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	In N,N-dimethyl acetamide; at 70℃;	General procedure: A mixture of acylhydrazine 1, 2 or alkylhydrazine 3 (10 mmol) and cyclic di- or triketones (<strong>[874-23-7]2-acetylcyclohexanone</strong> 19, 2-acetyl-1,3-cyclohexandione 20 or 2-acetyl-1,3-indandione 21) (10 mmol) in DMA was stirred at 70C for 4 to 8h, until the complete consumption of the reagents (reaction progress monitored by TLC). After cooling to rt, distilled water was added to the reaction media and the resulting solid was colected by filtration and purified by column chromatography on silica gel using EtOAc/n-C6H14 1/1 as eluent to afford purepyrazole (22-30).

Reference： [1]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 6896 - 6902,7

46
[ 874-23-7 ]
[ 125096-15-3 ]
[ 1414632-66-8 ]

Yield	Reaction Conditions	Operation in experiment
25%	In N,N-dimethyl acetamide; at 70.0℃;	General procedure: A mixture of acylhydrazine 1, 2 or alkylhydrazine 3 (10 mmol) and cyclic di- or triketones (2-acetylcyclohexanone 19, 2-acetyl-1,3-cyclohexandione 20 or 2-acetyl-1,3-indandione 21) (10 mmol) in DMA was stirred at 70C for 4 to 8h, until the complete consumption of the reagents (reaction progress monitored by TLC). After cooling to rt, distilled water was added to the reaction media and the resulting solid was colected by filtration and purified by column chromatography on silica gel using EtOAc/n-C6H14 1/1 as eluent to afford purepyrazole (22-30).

Reference： [1]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 6896 - 6902,7

47
[ 874-23-7 ]
[ 1599469-84-7 ]
[ 177911-87-4 ]
5-(4-isopropylsulfonylphenyl)-3-[3-[4-(pyrrolidin-2-ylmethylamino)phenyl]isoxazol-5-yl]pyrazin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;	Step 3: 5-(4-isopropylsulfonylphenyl)-3-[3-[4-(pyrrolidin-2-ylmethylamino)phenyl]isoxazol-5-yl]pyrazin-2-amine 1-5 A reaction mixture containing CuI (43.57 mg, 0.2288 mmol), Cs2CO3 (149.1 mg, 0.4576 mmol), 2-acetylcyclohexanone (64.15 mg, 0.4576 mmol), <strong>[177911-87-4]tert-butyl 2-(aminomethyl)pyrrolidine-1-carboxylate</strong> (137.5 mg, 0.6864 mmol) and 3-(3-(4-iodophenyl)isoxazol-5-yl)-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine (125 mg, 0.2288 mmol) in DMF (7.500 mL) was heated at 90 C. overnight. The reaction mixture was cooled to rt and partitioned between ethyl acetate (5 mL) and water (5 mL) and the layers separated. The aqueous layer was extracted further with ethyl acetate (25 mL) and the combined organic extracts were washed sequentially with water (15 mL) and brine (15 mL), dried over MgSO4 and concentrated in vacuo which yielded an oil. The oil was purified by reverse phase preparative HPLC [Waters Sunfire C18, 100 A column, 5 M, 19 mm150 mm, (solvent A: 0.05% TFA in water; solvent B: 0.05% TFA in CH3CN) over 16 minutes at 20 mL/min]. The product fractions were combined and concentrated to leave a yellow solid. The solid was dissolved in CH2Cl2(10 mL) and TFA (2 mL) was added and the resulting solution stirred at rt for 5 h. The reaction mixture was concentrated in vacuo and the residue partitioned between CH2Cl2 (5 mL) and water (5 mL) and the combined organic extracts were dried over MgSO4 and concentrated in vacuo which was purified by reverse phase preparative HPLC [Waters Sunfire C18, 100 A column, 5 M, 19 mm*150 mm, (solvent A: 0.05% TFA in water; solvent B: 0.05% TFA in CH3CN) over 16 minutes at 20 mL/min]. The product fractions were combined and concentrated to leave the title compound as a yellow solid (25 mg, 15% yield); 1H NMR (400.0 MHz, DMSO) d 1.19 (d, J=6.9 Hz, 6H), 1.68 (dd, J=8.2, 12.7 Hz, 1H), 1.93 (m, 2H), 2.15-2.11 (m, 1H), 3.23 (m, 2H), 3.45-3.39 (m, 1H), 3.56 (m, 1H), 3.71 (m, 2H), 6.80 (d, J=8.7 Hz, 2H), 7.18 (s, 1H), 7.65 (s, 1H), 7.80 (d, J=8.7 Hz, 2H), 7.94 (d, J=8.5 Hz, 2H), 8.38 (d, J=8.5 Hz, 2H), 8.47 (bs, 1H) and 8.94 (s, 2H) ppm; MS (ES+) 519.

Reference： [1]Patent: US2014/107093,2014,A1 .Location in patent: Page/Page column

48
[ 50-00-0 ]
[ 874-23-7 ]
[ 62-53-3 ]
2,4-bis-phenyl-2,4-diazaspiro[5.5]undecan-7-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; at 20℃; for 3.16667h;Reflux;	General procedure: A mixture of 4-methylaniline (1.0mmol), formaldehyde (9 equiv, 36% aq solution), DBU(1 equiv) and dimedone (1 equiv) in EtOH (20 mL) was refluxed for 10 min to dissolve all the reactants, and then the reaction mixture was stirred for 3h at r.t. The solvent was distilled off and the resulting residue was subjected to column chromatography on silica gel using petroleum ether-EtOAc (10:1) as eluent, to give the product 3f along with a small amount of 4f. In an analogous manner, using <strong>[874-23-7]2-acetylcyclohexanone</strong> (2.0 mmol) product 10b was isolated.

Reference： [1]Synlett,2013,vol. 24,p. 2768 - 2772

49
[ 50-00-0 ]
[ 874-23-7 ]
[ 106-49-0 ]
2,4-bis-(4-methylphenyl)-2,4-diazaspiro[5.5]undecan-7-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; at 20℃; for 3.16667h;Reflux;	General procedure: A mixture of 4-methylaniline (1.0mmol), formaldehyde (9 equiv, 36% aq solution), DBU(1 equiv) and dimedone (1 equiv) in EtOH (20 mL) was refluxed for 10 min to dissolve all the reactants, and then the reaction mixture was stirred for 3h at r.t. The solvent was distilled off and the resulting residue was subjected to column chromatography on silica gel using petroleum ether-EtOAc (10:1) as eluent, to give the product 3f along with a small amount of 4f. In an analogous manner, using <strong>[874-23-7]2-acetylcyclohexanone</strong> (2.0 mmol) product 10b was isolated.

Reference： [1]Synlett,2013,vol. 24,p. 2768 - 2772

50
[ 50-00-0 ]
[ 874-23-7 ]
[ 104-94-9 ]
2,4-bis(4-methoxyphenyl)-2,4-diazaspiro[5.5]undecan-7-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; at 20℃; for 3.16667h;Reflux;	General procedure: A mixture of 4-methylaniline (1.0mmol), formaldehyde (9 equiv, 36% aq solution), DBU(1 equiv) and dimedone (1 equiv) in EtOH (20 mL) was refluxed for 10 min to dissolve all the reactants, and then the reaction mixture was stirred for 3h at r.t. The solvent was distilled off and the resulting residue was subjected to column chromatography on silica gel using petroleum ether-EtOAc (10:1) as eluent, to give the product 3f along with a small amount of 4f. In an analogous manner, using <strong>[874-23-7]2-acetylcyclohexanone</strong> (2.0 mmol) product 10b was isolated.

Reference： [1]Synlett,2013,vol. 24,p. 2768 - 2772

51
[ 50-00-0 ]
[ 874-23-7 ]
[ 106-47-8 ]
[ 1399545-00-6 ]

Yield	Reaction Conditions	Operation in experiment
61%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; at 20℃; for 3.16667h;Reflux;	General procedure: A mixture of 4-methylaniline (1.0mmol), formaldehyde (9 equiv, 36% aq solution), DBU(1 equiv) and dimedone (1 equiv) in EtOH (20 mL) was refluxed for 10 min to dissolve all the reactants, and then the reaction mixture was stirred for 3h at r.t. The solvent was distilled off and the resulting residue was subjected to column chromatography on silica gel using petroleum ether-EtOAc (10:1) as eluent, to give the product 3f along with a small amount of 4f. In an analogous manner, using <strong>[874-23-7]2-acetylcyclohexanone</strong> (2.0 mmol) product 10b was isolated.

Reference： [1]Synlett,2013,vol. 24,p. 2768 - 2772

52
[ 127-07-1 ]
[ 874-23-7 ]
4-methyl-5,6,7,8-tetrahydrochinazoline-2-ol-3-oxide hydrochloride [ No CAS ]
4-methyl-5,6,7,8-tetrahydrochinazolin-2-ol-1-oxide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; water; at -15 - 20℃;	0.08 mol (6.08 g) hydroxy urea were dissolved in 40 ml of 2 M HCl, 40 ml of methanol were added and 0.08 mol (11.21 g) 2-acetylcyclohexanone were added dropwise under cooling at approximately -15 C., stirred one further hour and thereby warmed up to 20 C. This was carried out six times in total. The combined reaction mixtures were then evaporated at the rotary evaporator. The residue was suspended with acetone, the solid filtered off and washed with acetone. After drying 36.97 g crude product 1 were obtained which were suspended with 250 ml ethanol and hot filtered. The filtrate was evaporated until dryness and 20.87 g crude product 2 were obtained. This was solubilised in the boiling heat in 500 ml of ethanol, hot filtered, and the filtrate was combined with 800 ml tetrahydrofuran. The precipitated solid was filtered off and dried. 14.3 g of a product were obtained which contained 87% of the title compound and 13% ammonium chloride. [0249] IR (in substance, cm-1): 3135, 3044, 2937, 2875, 2805, 2706, 2426, 1743, 1572, 1501, 1443, 1403, 1345, 1288, 1260, 1235, 1150, 1122, 1086, 1041, 908, 883, 824, 740, 707, 669, 643, 605, 546, 514. [0250] CHN-elementary analysis: C, 43.63; H, 6.08; N, 14.66. [0251] Chloride content: 22.2% (m/m) [0252] 1H-NMR (DMSO-d6, 400 MHz): delta [ppm]=2.76 (m, 2H), 2.53 (s, 3H), 2.49 (m, 2H), 1.70 (m, 4H). From the NMR-spectrum was estimated that the product contained approximately 5% of the regioisomere 4-methyl-5,6,7,8-tetrahydrochinazolin-2-ol-1-oxide hydrochloride.

Reference： [1]Patent: US2014/162994,2014,A1 .Location in patent: Paragraph 0248-0252

53
[ 874-23-7 ]
[ 1315053-78-1 ]
2-fluoro-4-iodo-N-methyl-N-[2-(trimethylsilyl)ethoxymethyl]benzamide [ No CAS ]
(R)-3-(3-fluoro-4-{methyl[2-(trimethylsilyl)ethoxymethyl]carbamoyl}phenylamino)-tetrahydrofuran-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		The mixture of 4-amino-2-fluoro-Nmethylbenzamide(22) (1.68 g, 10 mmol) [35], H2SO4 (0.68 mL) andwater (13 mL) was gently heated until all the components werecompletely dissolved. The mixture was cooled to 0e5 understirring, then the solution of NaNO2 (0.7 g,10 mmol) inwater (2 mL)was added dropwise. The resulting mixture was stirred at 0e5for 0.5 h and then slowly poured into the solution of KI (5 g) in coldwater (20 mL). The solutionwas then heated up to 80 and stirredfor 0.5 h. After cooling it was treated with 30 mL of chloroform andfiltered. The organic layer was washed with 5% Na2SO3 solution,dried over Na2SO4 and rotovapped. Column chromatography onsilica gel (hexane/EtOAc 6:1) afforded 2.33 g (83%) of 2-fluoro-4-iodo-N-methylbenzamide (37). MS (ESI) [MH] 280. 1H NMR(400 MHz, DMSO-d6) d 8.25 (m, 1H), 7.73 (d, J 10.0 Hz, 1H), 7.65 (d,J 7.8 Hz, 1H), 7.37 (t, J 7.8 Hz, 1H), 2.75 (d, J 4.4 Hz, 3H). Thesolution of compound 37 (9 g, 32 mmol) in DMF (25 mL) was addedto the ice cooled suspension of NaH (1.48 g, 36.8 mmol, 60% in oil,washed with hexane) in DMF (50 mL). The resulting mixture wasvigorously stirred for 0.5 h in an ice bath, then SEM-chloride (6.46 g,39 mmol) was added and the mixture was continuously stirredovernight at the ambient temperature. After the reaction wascompleted, the mixture was poured into water (400 mL) and theobtained product was extracted with benzene (2 200 mL),washed with water, dried over Na2SO4 and then filtered through3 cm layer of silica gel washing with 5:1 hexane/EtOAc. The solventwas evaporated in vacuo providing 11 g (84%) of 2-fluoro-4-iodo-Nmethyl-N-[2-(trimethylsilyl)ethoxymethyl]benzamide (40). MS(ESI) [MH] 520. 1H NMR (400 MHz, CDCl3) d 7.58 (m,1H), 7.52 (m,1H), 7.12 (m, 1H), 5.01 (s, 0.8H), 4.58 (s, 1.2H), 3.63 (t, J 8.2 Hz,0.8H), 3.31 (t, J 8.2 Hz, 1.2H), 3.14 (s, 1.8H), 2.92 (d, J 0.8 Hz,1.2H), 0.99 (t, J 8.2 Hz, 0.8H), 0.82 (t, J 8.2 Hz, 1.2H), 0.04 (s,3.6), 0.01 (s, 5.4). The mixture of 6.69 g (51 mmol) of aminoacid(R)-36a or 9.55 g of (R)-36b, 17.4 g (42.5 mmol) of 40, 1.62 g(8.5 mmol) of CuI, 23.5 g (0.17 mol) of K2CO3, 36mL of water,145mLof DMF and 3e5 drops of Et3N was stirred for 10 min, then 6.56 g (46.8 mmol) of <strong>[874-23-7]2-acetylcyclohexanone</strong> was added and stirringcontinued at 100 for 24 h. After cooling the mixture was rotovapped,the residue was treated with 200mL of water and acidifiedwith hydrochloric acid to 2e3 (~30 mL). Then 200 mL of etherwas added, the mixture was stirred for 0.5 h and the formed precipitatewas filtered off, washed with 50 mL of ether and dried invacuo to give 10.7 g (65%) of (R)-3-(3-fluoro-4-{methyl[2-(trimethylsilyl)ethoxymethyl]carbamoyl}phenylamino)-tetrahydrofuran-3-carboxylic acid ((R)-41) (55% from ester (R)-36b). MS (ESI)[MH] 413. 1H NMR (400 MHz, DMSO-d6) d 12.97 (brs, 1H), 7.07(m, 2H), 6.31 (brs, 1H), 6.17 (brs, 1H), 4.85 (brs, 0.67H), 4.60 (brs,1.33H), 4.10 (brs, 1H), 3.87 (brs, 3H), 3.51 (brs, 0.67H), 3.24 (brs,1.33H), 2.93 (s, 2H), 2.86 (brs, 1H), 2.56 (brs, 1H), 2.16 (brs, 1H), 0.89(brs, 0.67H), 0.73 (brs, 1.33H), 0.03 (m, 9H). The mixture of 10.7 g(26 mmol) of (R)-41 and 8.9 g (39 mmol) of 4-isothiocyanato-2-(trifluoromethyl)benzonitrile (42) [34] in pyridine (100 mL) wasstirred at 80 for 48 h. The residue formed after cooling androtovapping was then treated with ethyl acetate and filteredthrough 2 cm layer of silica gel. The solvent was removed underreduced pressure and the desired product was crystallized fromethanol to obtain 4.85 g (30%) of 4-{(R)-3-[4-cyano-3-(trifluoromethyl)phenyl]-4-oxo-2-thioxo-7-oxa-1,3-diazaspiro[4.4]non-1-yl}-2-fluoro-N-methyl-N-[2-(trimethylsilyl)ethoxymethyl]benzamide ((R)-43). MS (ESI) [MH] 623. 1H NMR (400 MHz,CDCl3) d 8.01 (d, J 8.0 Hz, 1), 7.98 (s, 1), 7.85 (d, J 8.0 Hz, 1),7.57 (m, 1), 7.28 (m, 1), 7.21 (m, 1), 5.06 (s, 0.8), 4.63 (s, 1.2),4.41 (d, J 10.4 Hz, 1), 4.16 (d, J 10.4 Hz, 1), 3.97 (q, J 7.6 Hz,1), 3.78 (m, 1), 3.66 (t, J 8.2 Hz, 0.8), 3.66 (t, J 8.2 Hz, 1.2),3.20 (s, 1.8), 2.99 (s, 0.8), 2.72 (m, 1), 2.47 (m, 1), 1.01 (t,J 8.2 Hz, 0.8), 0.83 (t, J 8.2 Hz, 1.2), 0.06 (s, 3.6), 0.01 (s,5.4). TFA (15 mL) was added to the solution of compound (R)-43(4.8 g, 7.7 mmol) in DCM (30 mL), then the resulting mixture wasstirred for 3 h. The solvent was removed under reduced pressureand the formed residue was subjected to column chromatographyon silica gel (CHCl3/MeOH 60:1) to give 2.96 g (78%) of desiredproduct (R)-6.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 99,p. 51 - 66

54
[ 874-23-7 ]
[ 107-21-1 ]
[ 177-10-6 ]
[ 16111-99-2 ]
C₁₂H₂₀O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 44% 2: 8 %Chromat. 3: 6 %Chromat.	With toluene-4-sulfonic acid In chloroform Reflux; Dean-Stark; chemoselective reaction;	General procedure: In a typical experiment, a mixture of 15.0 g 2-acetylcyclohexanone(107 mmol), 6.64 g, ethylene glycol(107 mmol) and 0.22 g p-toluenesulfonic acid (1.3 mmol)in 200 cm3 chloroform was heated under reflux for 68 h in a Dean-Stark apparatus. The reaction mixture was cooled and then neutralised and washed with 0.3 M aqueous sodium hydroxide (3 9 60 cm3). The combined organic solution was dried on sodium sulfate and evaporated to dryness. The crude compound was subjected to column chromatography [silicagel 60 (Fluka), 0.035-0.070 mm],acetone/hexane (15/85). Yield: 8.72 g (44 %). The spectral data of 2 are in good agreement with those published previously [40].
1: 40 %Chromat. 2: 15 %Chromat. 3: 7 %Chromat.	With toluene-4-sulfonic acid In chloroform for 96h; Reflux; Dean-Stark; chemoselective reaction;	General procedure: In a typical experiment, a mixture of 15.0 g 2-acetylcyclohexanone(107 mmol), 6.64 g, ethylene glycol(107 mmol) and 0.22 g p-toluenesulfonic acid (1.3 mmol)in 200 cm3 chloroform was heated under reflux for 68 h in a Dean-Stark apparatus. The reaction mixture was cooled and then neutralised and washed with 0.3 M aqueous sodium hydroxide (3 9 60 cm3). The combined organic solution was dried on sodium sulfate and evaporated to dryness. The crude compound was subjected to column chromatography [silicagel 60 (Fluka), 0.035-0.070 mm],acetone/hexane (15/85). Yield: 8.72 g (44 %). The spectral data of 2 are in good agreement with those published previously [40].

Reference： [1]Farkas, Roland; Petz, Andea; Kollár, László [Monatshefte fur Chemie, 2015, vol. 146, # 10, p. 1665 - 1671]
[2]Farkas, Roland; Petz, Andea; Kollár, László [Monatshefte fur Chemie, 2015, vol. 146, # 10, p. 1665 - 1671]

55
[ 874-23-7 ]
[ 107-21-1 ]
[ 177-10-6 ]
[ 16111-99-2 ]
C₁₂H₂₀O₄ [ No CAS ]
C₁₂H₂₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 40 %Chromat. 2: 12 %Chromat. 3: 7 %Chromat. 4: 7 %Chromat.	With toluene-4-sulfonic acid In chloroform for 96h; Reflux; Dean-Stark; chemoselective reaction;	General procedure: In a typical experiment, a mixture of 15.0 g 2-acetylcyclohexanone(107 mmol), 6.64 g, ethylene glycol(107 mmol) and 0.22 g p-toluenesulfonic acid (1.3 mmol)in 200 cm3 chloroform was heated under reflux for 68 h in a Dean-Stark apparatus. The reaction mixture was cooled and then neutralised and washed with 0.3 M aqueous sodium hydroxide (3 9 60 cm3). The combined organic solution was dried on sodium sulfate and evaporated to dryness. The crude compound was subjected to column chromatography [silicagel 60 (Fluka), 0.035-0.070 mm],acetone/hexane (15/85). Yield: 8.72 g (44 %). The spectral data of 2 are in good agreement with those published previously [40].
1: 27 %Chromat. 2: 17 %Chromat. 3: 16 %Chromat. 4: 9 %Chromat.	With toluene-4-sulfonic acid In chloroform for 96h; Reflux; Dean-Stark; chemoselective reaction;	General procedure: In a typical experiment, a mixture of 15.0 g 2-acetylcyclohexanone(107 mmol), 6.64 g, ethylene glycol(107 mmol) and 0.22 g p-toluenesulfonic acid (1.3 mmol)in 200 cm3 chloroform was heated under reflux for 68 h in a Dean-Stark apparatus. The reaction mixture was cooled and then neutralised and washed with 0.3 M aqueous sodium hydroxide (3 9 60 cm3). The combined organic solution was dried on sodium sulfate and evaporated to dryness. The crude compound was subjected to column chromatography [silicagel 60 (Fluka), 0.035-0.070 mm],acetone/hexane (15/85). Yield: 8.72 g (44 %). The spectral data of 2 are in good agreement with those published previously [40].

Reference： [1]Farkas, Roland; Petz, Andea; Kollár, László [Monatshefte fur Chemie, 2015, vol. 146, # 10, p. 1665 - 1671]
[2]Farkas, Roland; Petz, Andea; Kollár, László [Monatshefte fur Chemie, 2015, vol. 146, # 10, p. 1665 - 1671]

56
[ 3248-05-3 ]
[ 874-23-7 ]
europium(III) chloride hexahydrate [ No CAS ]
Eu(AcCHex)₃*4,7-dimethylphenanthroline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In ethanol; water	2.1 Synthesis of the lanthanide CA complexes General procedure: In the preparation of the Ln(CA)3·Phn and Ln(CA)3·Bpy adducts the 3-N NaOH water solution and an ethanol solution of Phn or Bpy were added to an ethanol solution of CA. Then, a water-ethanol (1:1) solution of LnCl3·6H2O was drop by drop added to the previous mixture at heating in a water bath (at 60-70°C) or sometimes without heating. A molar ratio of the reagents CA: Phn (Bpy): lanthanide chloride: NaOH was equal to 3:1:1:3. The compound Eu(AcCHex)3·Phen was also synthesized by other method involving the preparation of an ethanol solution of a mixture of CA, Phen and EuCl3·6H2O in a molar ratio of 3:1:1 and adjusting the pH value of reaction mixture to 6 with a liquid ammonia. It should be pointed out that the heating of the reaction mixture results in a decrease in the keto/enol ratio of cycloalkanone [37] that promotes a binding of CA with the Ln3+ ion. At the same time, the probability of decomposition of cycloalkanonate anion increases.

Reference： [1]Zhuravlev; Kudryashova; Tsaryuk [Journal of Photochemistry and Photobiology A: Chemistry, 2016, vol. 314, p. 14 - 21]

57
[ 3248-05-3 ]
[ 874-23-7 ]
terbium(III) chloride hexahydrate [ No CAS ]
Tb(AcCHex)₃*4,7-dimethylphenanthroline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In ethanol; water	2.1 Synthesis of the lanthanide CA complexes General procedure: In the preparation of the Ln(CA)3·Phn and Ln(CA)3·Bpy adducts the 3-N NaOH water solution and an ethanol solution of Phn or Bpy were added to an ethanol solution of CA. Then, a water-ethanol (1:1) solution of LnCl3·6H2O was drop by drop added to the previous mixture at heating in a water bath (at 60-70°C) or sometimes without heating. A molar ratio of the reagents CA: Phn (Bpy): lanthanide chloride: NaOH was equal to 3:1:1:3. The compound Eu(AcCHex)3·Phen was also synthesized by other method involving the preparation of an ethanol solution of a mixture of CA, Phen and EuCl3·6H2O in a molar ratio of 3:1:1 and adjusting the pH value of reaction mixture to 6 with a liquid ammonia. It should be pointed out that the heating of the reaction mixture results in a decrease in the keto/enol ratio of cycloalkanone [37] that promotes a binding of CA with the Ln3+ ion. At the same time, the probability of decomposition of cycloalkanonate anion increases.

Reference： [1]Zhuravlev; Kudryashova; Tsaryuk [Journal of Photochemistry and Photobiology A: Chemistry, 2016, vol. 314, p. 14 - 21]

58
[ 3248-05-3 ]
[ 874-23-7 ]
gadolinium(III) chloride hexahydrate [ No CAS ]
Gd(AcCHex)₃*4,7-dimethylphenanthroline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In ethanol; water	2.1 Synthesis of the lanthanide CA complexes General procedure: In the preparation of the Ln(CA)3·Phn and Ln(CA)3·Bpy adducts the 3-N NaOH water solution and an ethanol solution of Phn or Bpy were added to an ethanol solution of CA. Then, a water-ethanol (1:1) solution of LnCl3·6H2O was drop by drop added to the previous mixture at heating in a water bath (at 60-70°C) or sometimes without heating. A molar ratio of the reagents CA: Phn (Bpy): lanthanide chloride: NaOH was equal to 3:1:1:3. The compound Eu(AcCHex)3·Phen was also synthesized by other method involving the preparation of an ethanol solution of a mixture of CA, Phen and EuCl3·6H2O in a molar ratio of 3:1:1 and adjusting the pH value of reaction mixture to 6 with a liquid ammonia. It should be pointed out that the heating of the reaction mixture results in a decrease in the keto/enol ratio of cycloalkanone [37] that promotes a binding of CA with the Ln3+ ion. At the same time, the probability of decomposition of cycloalkanonate anion increases.

Reference： [1]Zhuravlev; Kudryashova; Tsaryuk [Journal of Photochemistry and Photobiology A: Chemistry, 2016, vol. 314, p. 14 - 21]

59
[ 874-23-7 ]
[ 36651-36-2 ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 4063 - 4068

60
[ 749927-69-3 ]
[ 874-23-7 ]
3-(4-methylcarbamoyl-3-fluorophenylamino)tetrahydrofuran-3-encarboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine; In water;	EXAMPLE 1 The general method for preparation of 3-(4-methylcarbamoyl-3-fluorophenylamino)tetrahydrofuran-3-encarboxylic acid, its ester of the general formula 1 and stereoisomer thereof. In a round bottom flask provided with magnetic stirrer, reflux condenser and oil bath with a temperature controller, was placed 1.2 eq. of acid 3.1 or its ester of the general formula 3.2, 1 eq. of <strong>[749927-69-3]4-bromo-2-fluoro-N-methylbenzamide</strong> of the general formula 2, 0.35 g (0.15 eq.) of copper iodide (I), 6.76 g (4 eq.) of potassium carbonate, 6 ml of water, 27.5 ml of dimethylformamide, and 0.2 ml of triethylamine. After 10 min of stirring 0.35 g (0.2 eq.) of 2-acetylcyclohexanone was added. The reaction mixture was stirred at 100 C. for two days. After the reaction was completed solvents were distilled in vacuo. It gave ester of the general formula 1, wherein R1=Cl-C4alkyl, which was mixed with water and acidified with hydrochloric acid (conc.) till pH about 2-3. In 20-30 min. at stirring a solid was formed, which was filtered off, washed with water, and dried. Then it was washed with ether. It gave an acid of the general formula 1, where R1=H. Yield is above 80%. (R)-3-{4-[Methyl-(2-trimethylsilylethoxymethyl)carbamoyl]-3-fluorophenylamino}tetra hydrofuran-3-carboxylic acid 1 [R1=H, R2=CH2OCH2CH2Si(CH3)3] LC MS m/e 413 (M+1); 1H NMR (DMSO, 400 MHz) delta 12.85 (br. s, 1H), 7.05 (t, 1H), 6.97 (br. s, 1H), 6.30 (m, 1H), 6.15 (d, 1H), 4.84 (s, 1H), 4.60 (s, 1H), 4.09 (d, 1H), 3.88 (t, 3H), 3.50 (br. s, 1H), 3.32 (br. s, 1H), 2.90 (m, 3H), 2.56 (m, 1H), 2.16 (m, 1H), 0.87 (br. s, 1H), 0.76 (br. s, 1H), 0.00 (m, 9H). (R)-3-(4-Methylcarbamoyl-3-fluorophenylamino)tetrahydrofuran-3-encarboxylic acid 1(1), LC MS m/e 283 (M+1); 1H NMR (DMSO, 400 MHz) delta 13.01 (br. s, 1H), 7.68 (s, 1H), 7.46 (t, 1H), 7.13 (s, 1H), 6.31 (d, 1H), 6.11 (d,1H), 4.09 (d, 1H), 3.86 (m, 3H), 2.71 (m, 4H), 2.14 (m, 1H).

Reference： [1]Patent: US2016/16925,2016,A1

61
[ 874-23-7 ]
[ 5369-16-4 ]
[ 7766-63-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With 2,2'-azobis(isobutyronitrile); oxygen; In acetonitrile; at 80℃; for 24h;Sealed tube;	General procedure: A sealed tube was equipped with a magnetic stir bar was charged with 1,3-di-ketone 1a (0.075 g, 0.75 mmol), aniline 2a (0.0232 g, 0.25 mmol), AIBN (0.0164 g, 0.0001 mmol), and acetonitrile (1.0 mL). The above reaction mixture was stirred at 80C under O2 atmosphere for 24 h. After completion of the reaction, the reaction was then cooled to room temperature, mixture was diluted with ethyl acetate. After removal of the solvent under reduced pressure the left out residue was purified by column chromatography using silica gel with hexane and ethyl acetate as eluent to get 3a in 82% yield (0.0278 g). The spectral data was well matched with reported values. The above procedure is followed for the synthesis of all products reported in this manuscript.

Reference： [1]Tetrahedron,2016,vol. 72,p. 4889 - 4894

62
[ 455-14-1 ]
[ 874-23-7 ]
[ 349-97-3 ]

Yield	Reaction Conditions	Operation in experiment
50%	With 2,2'-azobis(isobutyronitrile); oxygen; In acetonitrile; at 80℃; for 24h;Sealed tube;	General procedure: A sealed tube was equipped with a magnetic stir bar was charged with 1,3-di-ketone 1a (0.075 g, 0.75 mmol), aniline 2a (0.0232 g, 0.25 mmol), AIBN (0.0164 g, 0.0001 mmol), and acetonitrile (1.0 mL). The above reaction mixture was stirred at 80C under O2 atmosphere for 24 h. After completion of the reaction, the reaction was then cooled to room temperature, mixture was diluted with ethyl acetate. After removal of the solvent under reduced pressure the left out residue was purified by column chromatography using silica gel with hexane and ethyl acetate as eluent to get 3a in 82% yield (0.0278 g). The spectral data was well matched with reported values. The above procedure is followed for the synthesis of all products reported in this manuscript.

Reference： [1]Tetrahedron,2016,vol. 72,p. 4889 - 4894

63
[ 874-23-7 ]
[ 30273-11-1 ]
[ 20331-25-3 ]

Yield	Reaction Conditions	Operation in experiment
58%	With 2,2'-azobis(isobutyronitrile); oxygen; In acetonitrile; at 80℃; for 24h;Sealed tube;	General procedure: A sealed tube was equipped with a magnetic stir bar was charged with 1,3-di-ketone 1a (0.075 g, 0.75 mmol), aniline 2a (0.0232 g, 0.25 mmol), AIBN (0.0164 g, 0.0001 mmol), and acetonitrile (1.0 mL). The above reaction mixture was stirred at 80C under O2 atmosphere for 24 h. After completion of the reaction, the reaction was then cooled to room temperature, mixture was diluted with ethyl acetate. After removal of the solvent under reduced pressure the left out residue was purified by column chromatography using silica gel with hexane and ethyl acetate as eluent to get 3a in 82% yield (0.0278 g). The spectral data was well matched with reported values. The above procedure is followed for the synthesis of all products reported in this manuscript.

Reference： [1]Tetrahedron,2016,vol. 72,p. 4889 - 4894

64
[ 874-23-7 ]
3-methyl-4,5,6,7-tetrahydro-2H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydrazine hydrate; In neat (no solvent); at 150℃; for 0.0333333h;Microwave irradiation; Green chemistry;	The Knorr pyrazole synthesis is the reaction of hydrazine or substituted hydrazine with 1,3-dicarbonyl compounds to provide the pyrazole or pyrazolone ring system. Dimethylformamide(DMF) and acetic acid (AcOH) were used in the conventional method for the purpose of comparingthe influence of the solvent on yield and reaction time. Method A (Reflux)(a) A mixture of <strong>[874-23-7]2-acetylcyclohexanone</strong> (1, 1 mmol), and hydrazines 2 (1.0 mmol) in DMF (10 mL)was heated under reflux for 6-8 h. The precipitated solid product was filtered, washed with ethanol (EtOH), dried and finally recrystallized from DMF. (b) <strong>[874-23-7]2-Acetylcyclohexanone</strong> (1, 1 mmol) and hydrazines 2 (1.0 mmol) in AcOH (10 mL) were stirredat 80 C for the given times. After completion of the reaction, the mixture was cooled to room temperature and the precipitate was filtered and purified by recrystallization from EtOH. Method B (MW)A mixture of <strong>[874-23-7]2-acetylcyclohexanone</strong> (1, 1.0 mmol) and hidrazines 2 (1.0 mmol) was subjected to microwave irradiation (Scheme 1). The solid products were isolated by crystallization of the reaction mixture from EtOH and washed with a mixture of hexane/ethanol (7:3) to get the corresponding compounds. Hydrazines used to obtain compounds 3c-f was applied as the corresponding hydrochloride.

Reference： [1]Molecules,2016,vol. 21

65
[ 874-23-7 ]
[ 589-21-9 ]
[ 64486-26-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	In neat (no solvent) at 150℃; for 0.166667h; Microwave irradiation; regioselective reaction;	2.2. General procedure synthesis General procedure: A mixture of 1,3-dione (1 mmol) 1a -d and hydrazine deriva- tive (1 mmol) 2a -i was subjected to solvent free microwave ir- radiation (150 °C, 10 min). Azoles 3a -ac were readily purified by column chromatography using 5-20% EtOAc-hexanes as eluent. The synthesized compounds with their physical data are listed below.
47%	In N,N-dimethyl-formamide for 7h; Reflux;	The Knorr pyrazole synthesis is the reaction of hydrazine or substituted hydrazine with 1,3-dicarbonyl compounds to provide the pyrazole or pyrazolone ring system. Dimethylformamide(DMF) and acetic acid (AcOH) were used in the conventional method for the purpose of comparingthe influence of the solvent on yield and reaction time. Method A (Reflux)(a) A mixture of 2-acetylcyclohexanone (1, 1 mmol), and hydrazines 2 (1.0 mmol) in DMF (10 mL)was heated under reflux for 6-8 h. The precipitated solid product was filtered, washed with ethanol (EtOH), dried and finally recrystallized from DMF. (b) 2-Acetylcyclohexanone (1, 1 mmol) and hydrazines 2 (1.0 mmol) in AcOH (10 mL) were stirredat 80 °C for the given times. After completion of the reaction, the mixture was cooled to room temperature and the precipitate was filtered and purified by recrystallization from EtOH. Method B (MW)A mixture of 2-acetylcyclohexanone (1, 1.0 mmol) and hidrazines 2 (1.0 mmol) was subjected to microwave irradiation (Scheme 1). The solid products were isolated by crystallization of the reaction mixture from EtOH and washed with a mixture of hexane/ethanol (7:3) to get the corresponding compounds. Hydrazines used to obtain compounds 3c-f was applied as the corresponding hydrochloride.

Reference： [1]Galdámez, Antonio; Gutiérrez, Margarita; Henao, José A.; Morales-Bayuelo, Alejandro; Núñez, Yeray A. Rodríguez; Polo, Efraín; Prent-Peñaloza, Luis; Ramos, Juan; Trilleras, Jorge; Valdés-Salas, Lady [Journal of Molecular Structure, 2021, vol. 1224]
[2]Polo, Efrain; Trilleras, Jorge; Ramos, Juan; Galdámez, Antonio; Quiroga, Jairo; Gutierrez, Margarita [Molecules, 2016, vol. 21, # 7]

66
[ 874-23-7 ]
[ 622-88-8 ]
[ 64486-26-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	In neat (no solvent); at 150℃; for 0.0333333h;Microwave irradiation; Green chemistry;	The Knorr pyrazole synthesis is the reaction of hydrazine or substituted hydrazine with 1,3-dicarbonyl compounds to provide the pyrazole or pyrazolone ring system. Dimethylformamide(DMF) and acetic acid (AcOH) were used in the conventional method for the purpose of comparingthe influence of the solvent on yield and reaction time. Method A (Reflux)(a) A mixture of <strong>[874-23-7]2-acetylcyclohexanone</strong> (1, 1 mmol), and hydrazines 2 (1.0 mmol) in DMF (10 mL)was heated under reflux for 6-8 h. The precipitated solid product was filtered, washed with ethanol (EtOH), dried and finally recrystallized from DMF. (b) <strong>[874-23-7]2-Acetylcyclohexanone</strong> (1, 1 mmol) and hydrazines 2 (1.0 mmol) in AcOH (10 mL) were stirredat 80 C for the given times. After completion of the reaction, the mixture was cooled to room temperature and the precipitate was filtered and purified by recrystallization from EtOH. Method B (MW)A mixture of <strong>[874-23-7]2-acetylcyclohexanone</strong> (1, 1.0 mmol) and hidrazines 2 (1.0 mmol) was subjected to microwave irradiation (Scheme 1). The solid products were isolated by crystallization of the reaction mixture from EtOH and washed with a mixture of hexane/ethanol (7:3) to get the corresponding compounds. Hydrazines used to obtain compounds 3c-f was applied as the corresponding hydrochloride.

Reference： [1]Molecules,2016,vol. 21

67
[ 874-23-7 ]
[ 24589-77-3 ]
4-(3-methyl-4,5,6,7-tetrahydro-2H-indazol-2-yl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	In neat (no solvent); at 150℃; for 0.0333333h;Microwave irradiation; Green chemistry;	The Knorr pyrazole synthesis is the reaction of hydrazine or substituted hydrazine with 1,3-dicarbonyl compounds to provide the pyrazole or pyrazolone ring system. Dimethylformamide(DMF) and acetic acid (AcOH) were used in the conventional method for the purpose of comparingthe influence of the solvent on yield and reaction time. Method A (Reflux)(a) A mixture of 2-acetylcyclohexanone (1, 1 mmol), and hydrazines 2 (1.0 mmol) in DMF (10 mL)was heated under reflux for 6-8 h. The precipitated solid product was filtered, washed with ethanol (EtOH), dried and finally recrystallized from DMF. (b) 2-Acetylcyclohexanone (1, 1 mmol) and hydrazines 2 (1.0 mmol) in AcOH (10 mL) were stirredat 80 C for the given times. After completion of the reaction, the mixture was cooled to room temperature and the precipitate was filtered and purified by recrystallization from EtOH. Method B (MW)A mixture of 2-acetylcyclohexanone (1, 1.0 mmol) and hidrazines 2 (1.0 mmol) was subjected to microwave irradiation (Scheme 1). The solid products were isolated by crystallization of the reaction mixture from EtOH and washed with a mixture of hexane/ethanol (7:3) to get the corresponding compounds. Hydrazines used to obtain compounds 3c-f was applied as the corresponding hydrochloride.

Reference： [1]Molecules,2016,vol. 21

68
[ 874-23-7 ]
[ 823-85-8 ]
2-(4-fluorophenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	In neat (no solvent); at 150℃; for 0.0333333h;Microwave irradiation; Green chemistry;	The Knorr pyrazole synthesis is the reaction of hydrazine or substituted hydrazine with 1,3-dicarbonyl compounds to provide the pyrazole or pyrazolone ring system. Dimethylformamide(DMF) and acetic acid (AcOH) were used in the conventional method for the purpose of comparingthe influence of the solvent on yield and reaction time. Method A (Reflux)(a) A mixture of <strong>[874-23-7]2-acetylcyclohexanone</strong> (1, 1 mmol), and hydrazines 2 (1.0 mmol) in DMF (10 mL)was heated under reflux for 6-8 h. The precipitated solid product was filtered, washed with ethanol (EtOH), dried and finally recrystallized from DMF. (b) <strong>[874-23-7]2-Acetylcyclohexanone</strong> (1, 1 mmol) and hydrazines 2 (1.0 mmol) in AcOH (10 mL) were stirredat 80 C for the given times. After completion of the reaction, the mixture was cooled to room temperature and the precipitate was filtered and purified by recrystallization from EtOH. Method B (MW)A mixture of <strong>[874-23-7]2-acetylcyclohexanone</strong> (1, 1.0 mmol) and hidrazines 2 (1.0 mmol) was subjected to microwave irradiation (Scheme 1). The solid products were isolated by crystallization of the reaction mixture from EtOH and washed with a mixture of hexane/ethanol (7:3) to get the corresponding compounds. Hydrazines used to obtain compounds 3c-f was applied as the corresponding hydrochloride.

Reference： [1]Molecules,2016,vol. 21

69
[ 874-23-7 ]
[ 100-63-0 ]
[ 14713-75-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	In neat (no solvent); at 150℃; for 0.0333333h;Microwave irradiation; Green chemistry;	The Knorr pyrazole synthesis is the reaction of hydrazine or substituted hydrazine with 1,3-dicarbonyl compounds to provide the pyrazole or pyrazolone ring system. Dimethylformamide(DMF) and acetic acid (AcOH) were used in the conventional method for the purpose of comparingthe influence of the solvent on yield and reaction time. Method A (Reflux)(a) A mixture of <strong>[874-23-7]2-acetylcyclohexanone</strong> (1, 1 mmol), and hydrazines 2 (1.0 mmol) in DMF (10 mL)was heated under reflux for 6-8 h. The precipitated solid product was filtered, washed with ethanol (EtOH), dried and finally recrystallized from DMF. (b) <strong>[874-23-7]2-Acetylcyclohexanone</strong> (1, 1 mmol) and hydrazines 2 (1.0 mmol) in AcOH (10 mL) were stirredat 80 C for the given times. After completion of the reaction, the mixture was cooled to room temperature and the precipitate was filtered and purified by recrystallization from EtOH. Method B (MW)A mixture of <strong>[874-23-7]2-acetylcyclohexanone</strong> (1, 1.0 mmol) and hidrazines 2 (1.0 mmol) was subjected to microwave irradiation (Scheme 1). The solid products were isolated by crystallization of the reaction mixture from EtOH and washed with a mixture of hexane/ethanol (7:3) to get the corresponding compounds. Hydrazines used to obtain compounds 3c-f was applied as the corresponding hydrochloride.

Reference： [1]Molecules,2016,vol. 21
[2]Synlett,2018,vol. 29,p. 2689 - 2692

70
[ 874-23-7 ]
[ 10300-69-3 ]
2-chloromethyl-5,6,7,8-tetrahydro-4-methylquinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58.9%	With potassium carbonate; In butan-1-ol; for 5h;Reflux;	2-acetylcyclohexanone (2.8 g, 20 mmol), potassium carbonate (4.1 g, 30 mmol) and <strong>[10300-69-3]chloroacetamidine hydrochloride</strong> (2.8 g, 22 mmol) were added to 30 mL of n-butanol and stirred under reflux for 5 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. The residue was poured into 50 mL of water and extracted with ethyl acetate (30 mL × 3). The combined organic phase was washed once with 30 mL of saturated aqueous sodium chloride, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a yellow solid which was purified by column chromatography to give a pale yellow liquid, 2.3 g, in 58.9% yield.
58.9%	With potassium carbonate; In butan-1-ol; for 5h;Reflux;	2-acetyl-cyclohexanone (2.8g, 20mmol), potassium carbonate (4.1g, 30mmol) and chloro-acetamidine hydrochloride (2.8g, 22mmol) was added to 30mL of n-butanol, stirred at reflux for 5 hours.The reaction was completed, the solvent was distilled off under reduced pressure, the residue was poured into 50mL water and extracted with ethyl acetate (30mL, extracted three times) and the combined organic phase was washed with 30mL saturated brine once, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure a yellow solid was purified by column chromatography (eluent: petroleum ether / ethyl acetate = 9: 1) to give a pale yellow liquid 2.3g, yield 58.9%.

Reference： [1]Patent: CN103848811,2016,B .Location in patent: Paragraph 0237;0238; 0239; 0240; 0241
[2]Patent: CN103709163,2016,B .Location in patent: Paragraph 0191-0194

71
[ 874-23-7 ]
[1-[2-bromo-5-(trifluoromethyl)phenyl]cyclopentyl]methanamine [ No CAS ]
5'-(trifluoromethyl)spiro[cyclopentane-1,3'-indoline] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With copper(l) iodide; potassium carbonate; caesium carbonate; In N,N-dimethyl-formamide; at 60℃; for 3h;Schlenk technique;	In a Schienk tube, 2 g of [1-[2-bromo-5-(trifluo- romethyl) phenyl]cycloentyl]menthanamine (preparation 189; 6.56 mmol; 1 eq), 242mg of Cul (1.27 mmol; 0.2 eq), 268 mg of 2-acetylyclohexanone (1.91 mmol; 0.3 eq), 414 mg of cesium carbonate (1.27 mmol; 0.2 eq) and 1.583 g of K2C03 (11.45 mmol; 1.8 eq) were added to 4 mEofDMF. The reaction medium was stirred for 3 h at 60 C. After the addition of EtOAc, the oorganic phase was washed with water,then dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica using a cyclohexane/1% to 30% ethyl acetate gradient, to give 1025mg of the title compound in the form of a yellow liquid.11561] Yld: 67%.11562] ?H NMR (300 MHz, CHC13-d) oeppm 1.65-1.78 (m, 2H) 1.78-1.93 (m, 6H) 3.43 (m, 2H) 3.96 (ibrs, 1H) 6.60 (d, J=8.1 Hz, 1H) 7.21-7.24 (m, 1H) 7.27 (dd, J=8.1, 1.9 Hz, 1H).11563] EC-MS: m/z (M+H): 431.

Reference： [1]Patent: US2017/66717,2017,A1 .Location in patent: Paragraph 1560-1563

72
[ 874-23-7 ]
[ 626-15-3 ]
2,2'-(1,3-phenylenebis(methylene))bis(2-acetylcyclohexan-1-one) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		A round bottom flask equipped with a stirring bar is charged at room temperature with 2- acetylcyclohexanone (350 mg, 2.5 mmol, 2.5 equiv.) 1 ,2-dimethoxyethane (2 ml), Kl (332 mg, 2.0 mmol, 2 equiv.) alpha,alpha'-dibromo-m-xylene (263 mg, 1.0 mmol, 1.0 equiv.). After 5 min under vigorous stirring, was added to the mixture freshly powdered anhydrous K2CO3 (344 mg, 2.5 mmol, 2.5 equiv.). The suspension was allowed to stir at reflux for 17 h, after that was allowed to cool down to room temperature and diluted with diethylether (2 ml). The suspension was filtered through a fritted plate and the solids were thoughtfully washed with acetone (2 x 5 ml) and ethylacetate (2 x 5 ml). The yellow filtrate solution was concentrated in in vacuo (rotavapor and high vacuum) affording a yellow oily solid that was recrystallized from methanol affording 2,2'-(1 ,3-phenylenebis(methylene))bis(2- acetylcyclohexan-1-one) 3 as a white solid mixture of isomers (264 mg, 69%, 0.69 mmol). 1H NMR (400 MHz, CDCI3) delta = 7.13 (t, J = 7.6 Hz, 1 H), 6.93 (td, J = 7.4, 1.8 Hz, 2H), 6.86 - 6.77 (m, 1 H), 3.16 - 3.02 (m, 4H), 2.58 - 2.49 (m, 2H), 2.40 - 2.20 (m, 4H), 2.14-2.07 (m, 6H), 2.04 - 1.93 (m, 2H), 1.78 - 1.54 (m, 6H), 1.40 (m, 2H). 13C NMR (101 MHz, CDCU) delta = 209.8, 209.8, 136.6, 136.5, 132.8, 132. , 129.2, 129.2, 128.2, 128.4, 69.1 , 42.5, 42.4, 40.2,, 34.3, 34.2, 27.4, 27.4, 27.3, 27.2, 22.6, 22.6. - HRMS (ESI-TOF) calc'd for [C24H30O4 + H]+ 383.2217; found 383.2215.
69%		A round bottom flask equipped with a stirring bar is charged at room temperature with 2- acetylcyclohexanone (350 mg, 2.5 mmol, 2.5 equiv.) 1 ,2-dimethoxyethane (2 ml), Kl (332 mg, 2.0 mmol, 2 equiv.) alpha,alpha'-dibromo-m-xylene (263 mg, 1.0 mmol, 1.0 equiv.). After 5 min under vigorous stirring, was added to the mixture freshly powdered anhydrous K2C03 (344 mg, 2.5 mmol, 2.5 equiv.). The suspension was allowed to stir at reflux for 17 h, after that was allowed to cool down to room temperature and diluted with diethylether (2 ml). The suspension was filtered through a fritted plate and the solids were thoughtfully washed with acetone (2 x 5 ml) and ethylacetate (2 x 5 ml). The yellow filtrate solution was concentrated in in vacuo (rotavapor and high vacuum) affording a yellow oily solid that was recrystallized from methanol affording 2,2'-(1 ,3-phenylenebis(methylene))bis(2- acetylcyclohexan-1-one) 3 as a white solid mixture of isomers (264 mg, 69%, 0.69 mmol). H NMR (400 MHz, CDCI3) delta = 7.13 (t, J = 7.6 Hz, 1 H), 6.93 (td, J = 7.4, 1.8 Hz, 2H), 6.86 - 6.77 (m, 1 H), 3.16 - 3.02 (m, 4H), 2.58 - 2.49 (m, 2H), 2.40 - 2.20 (m, 4H), 2.14-2.07 (m, 6H), 2.04 - 1.93 (m, 2H), 1.78 - 1.54 (m, 6H), 1.40 (m, 2H). 13C NMR (101 MHz, CDCb) delta = 209.8, 209.8, 136.6, 136.5, 132.8, 132. , 129.2, 129.2, 128.2, 128.4, 69.1 , 42.5, 42.4, 40.2,, 34.3, 34.2, 27.4, 27.4, 27.3, 27.2, 22.6, 22.6. HRMS (ESI-TOF) calc'd for [C24H30O4 + H]+ 383.2217; found 383.2215.

Reference： [1]Patent: WO2017/129991,2017,A2 .Location in patent: Page/Page column 44-45
[2]Patent: WO2019/25575,2019,A1 .Location in patent: Page/Page column 51-52

73
[ 874-23-7 ]
[ 1446518-33-7 ]
3-(3-(1-acetyl-2-oxocyclohexyl)prop-1-en-2-yl)-3-methylpentane-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tris-(dibenzylideneacetone)dipalladium(0); xantphos; In 1,4-dioxane; at 80℃; for 2h;Inert atmosphere; Sealed tube;	General procedure: Carbonate 14 (0.24 mmol), Pd2(dba)3 (11 mg, 0.012 mmol), DPEphos(13.1 mg, 0.024 mmol) and the 1,3-dicarbonyl nucleophile (0.24mmol) were added to a dried tube under argon. The tube was fitted with a septum and purged further with argon. 1,4-Dioxane (1.5 mL)was added and the sealed tube was placed in an oil bath preheated to 80 C. The mixture was stirred at 80 C for 2 h, then cooled to roomtemperature, concentrated in vacuo and purified by flash column chromatography. Regioselectivity and chemoselectivity ratios were determined by 1H NMR

Reference： [1]Synthesis,2018,vol. 50,p. 1796 - 1814

74
[ 874-23-7 ]
[ 109-63-7 ]
[ 4181-05-9 ]
C₄₆H₃₇BF₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%		In a 50 ml. flask, the mixture of <strong>[874-23-7]2-acetylcyclohexanone</strong> (193 muIota_, 1.463 mmol, 1 eq) and BF3 Et20 (199 muIota_, 1.609 mmol, 1.1 eq) in 3ml_ ethyl acetate was heated for 30min at 50-60C in air. Dissolved 4-(N,N-Diphenylamino)-benzaldehyde (1 g, 3.658 mmol, 2.5 eq) and B(n-OBu)3 (0.987 ml_, 3.658 mmol, 2.5 eq) into 12 mL ethyl acetate, then the solution was injected into the first mixture. Kept the reaction at 50-60C for another 30 min. Morpholine (101 muIota_, 1.170 mmol, 0.8 eq) was added dropwise into the reaction. The reaction was kept heating at 50-60C overnight. All the solvents were evaporated. The crude product could be obtained by flash column chromatography (silica, CH2CI2) mixed with few ligand and aldehyde. The further purification was done by many times' precipitation in CH2CI2/petroleum ether, giving dark green powder (860 mg, 84% yield). (0332) 1H NMR (400 MHz, CDCI3, ppm): 58.05 (d, J = 15.2 Hz, 1 H), 8.02 (s, 1 H), 7.47 (d, J = 8.8 Hz, 2H), 7.39-7.29 (m, 10H), 7.18-7.10 (m, 12H), 7.01 (d, J = 8.8 Hz, 2H), 6.99 (d, J = 8.8 Hz, 2H), 6.84 (d, J = 15.2 Hz, 1 H), 2.81 (t, J = 5.3 Hz, 2H), 2.65 (t, J = 6.0 Hz, 2H), 1.86-1.84 (m, 2H). (0333) 13C NMR (100 MHz, CDCI3, ppm): 5 151.4, 149.3, 147.6, 146.6, 146.2, 140.0, 132.7, 130.9, 129.6, 129.5, 128.4, 128.2, 126.0, 125.7, 124.9, 124.4, 120.7, 120.5, 113.7, 27.1 , 23.4, 22.1. HRMS (ESI+) [M + H]+ calcd for C46H38N202BF2+ m/z= 699.2994, found m/z= 699.2995.

Reference： [1]Patent: WO2018/155724,2018,A1 .Location in patent: Page/Page column 64-65

75
[ 874-23-7 ]
[ 88-05-1 ]
C₂₆H₃₄N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With toluene-4-sulfonic acid; In toluene; at 160℃;Inert atmosphere; Dean-Stark;	Under a argon atmosphere, 150 mL of toluene was added to a 300 mL round bottom flask. Further, 85.5 mmol of 2,4,6-trimethylaniline, 39.6 mmol of <strong>[874-23-7]2-acetylcyclohexanone</strong> and 80.4 mmol of p-toluenesulfonic acid were added, and the mixture was refluxed at 160 C for 4-5 days in a Dean-Stark apparatus, and the reaction was completed. After that, it was extracted, extracted with dichloromethane and saturated NaHCO3 three times, and the organic phase was dried over anhydrous MgSO 4 and evaporated and then evaporated with methanol. The obtained solid was an asymmetric diimine ligand with a yield of 58%.

Reference： [1]Patent: CN108569984,2018,A .Location in patent: Paragraph 0045; 0046

76
iron(III) chloride [ No CAS ]
[ 874-23-7 ]
tris(2-acetylcyclohexanonato)iron(III) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium hydroxide; In ethanol; water; at 60℃; for 1h;	General procedure: For the synthesis of 3a-c, NaOH (0.22?g, 5.7?mmol) was added to an aqueous solution (15?mL) of FeCl3 (0.31?g, 1.9?mmol). This mixture was added drop-wise to the respective beta-diketones (5.7?mmol) dissolved in 20?mL of ethanol at ambient temperature. The reaction mixture was allowed to stir for 1?h at 60?C. Afterwards, the solution was filtered off and the formed precipitate was washed with water (twice, 30?mL each) and dried in vacuum. Complexes 3a-c were obtained as red solids.

Reference： [1]Inorganica Chimica Acta,2019,vol. 487,p. 1 - 8

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	874-23-7	MDL No. :	MFCD00001633
Formula :	C₈H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OEKATORRSPXJHE-UHFFFAOYSA-N
M.W :	140.18	Pubchem ID :	13400
Synonyms :

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	38.86
TPSA :	34.14 Å²

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) :	-6.52 cm/s

Log Po/w (iLOGP) :	1.32
Log Po/w (XLOGP3) :	0.89
Log Po/w (WLOGP) :	1.33
Log Po/w (MLOGP) :	0.65
Log Po/w (SILICOS-IT) :	1.95
Consensus Log Po/w :	1.23

[ CAS No. 874-23-7 ] {[proInfo.proName]}

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[ 874-23-7 ] Synthesis Path-Downstream 1~76

Precautionary Statements-General

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Inquiry

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

Log S (ESOL) :	-1.2
Solubility :	8.77 mg/ml ; 0.0625 mol/l
Class :	Very soluble
Log S (Ali) :	-1.19
Solubility :	9.02 mg/ml ; 0.0643 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.51
Solubility :	4.29 mg/ml ; 0.0306 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.89

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H227-H315-H319-H335	Packing Group:	N/A
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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