Name: 19694-02-1|1-Pyrenecarboxylic acid|97%
Brand: Ambeed
SKU: A839102
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1
[ 3029-19-4 ]
[ 19694-02-1 ]

Yield	Reaction Conditions	Operation in experiment
80.39%	With potassium permanganate; In water; acetone; at 80℃; for 3h;	First weighed 2.09g(About 0.0091 mol) pyrene Formaldehyde was placed in a round bottom flask,After adding 20.0ml of acetone dissolved.To a round bottom flask was added KMnO4 5.0g,Continue to add 15.0ml of deionized water to dissolve,Stir well.The round bottom flask was placed in an oil bath at 80 heating 3h,After the reaction is completed,Cool and filter.A sufficient amount of sodium carbonate was added to the filtrate until the filtrate had a pH of 8.5,And washed three times with CH 2 Cl 2 to remove unreacted starting material.Liquid separation,Take water solution.With dilute hydrochloric acid solution pH is adjusted to about 2.0,At this time a large number of precipitation precipitation,Filtered to give a precipitate.1.8 g was obtained after vacuum drying the precipitate(About 0.0073 mol)Pyrene formic acid,The yield is 80.39%.
62.6%	With potassium permanganate; water; In acetone; at 80℃; for 3h;	To a solution of 1-pyrenecarboxaldehyde (1.5 g, 6.5 mmol) in dryacetone (20.0 mL), potassium permanganate (4.0 g) dissolved indistilled water (20.0 mL) was added. The resulting mixture was refluxedat 80 C for 3 h, under the monitoring of thin-layer chromatography(TLC). Thereafter, the mixture was cooled to room temperature andfiltered. The filtrate was then adjusted to a pH of ~8.5 with sodiumcarbonate solution, and washed with dichloromethane three times toremove unreacted raw material. The aqueous solution was adjusted a pHof ~2.0 with dilute hydrochloric acid, and solid precipitate appeared.The precipitate was collected and vacuum-dried to obtain light yellowsolids (1.0 g, 62.6%).

Reference： [1]Bulletin of the Chemical Society of Japan,2012,vol. 85,p. 902 - 911
[2]Patent: CN107286038,2017,A .Location in patent: Paragraph 0060; 0061
[3]Dyes and Pigments,2020,vol. 174
[4]Chemische Berichte,1964,vol. 97,p. 349 - 362
[5]Carbohydrate Research,1989,vol. 192,p. 147 - 158
[6]Chemical and Pharmaceutical Bulletin,1999,vol. 47,p. 151 - 155
[7]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2020,vol. 239

2
[ 3264-21-9 ]
[ 19694-02-1 ]

Yield	Reaction Conditions	Operation in experiment
78.4%	With pyridine; sodium hypochlorite; In 1,2-dichloro-ethane; at 80℃; for 24h;	The compound II (24.3 g, 100 mmol), sodium hypochlorite (29.8 g, 400 mmol), pyridine (23.7 g, 300 mmol), and dichloroethane (243.3 g) were put in a flask and dissolved. The solution was heated at 80 C. and agitated for 24 hours, and an HCl aqueous solution was added thereto for neutralization. Then, an organic layer was separated and concentrated, obtaining 19.2 g (78.4% of a yield) of a compound (III).

Reference： [1]Patent: US2014/186777,2014,A1 .Location in patent: Paragraph 0079
[2]Journal of Organic Chemistry,1996,vol. 61,p. 9494 - 9502
[3]Chemistry - A European Journal,2003,vol. 9,p. 1922 - 1932
[4]Magnetic Resonance in Chemistry,1985,vol. 23,p. 150 - 155

3
[ 19694-02-1 ]
[ 16331-58-1 ]

Yield	Reaction Conditions	Operation in experiment
85.8%	With oxalyl dichloride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; at 60℃; for 12h;	The compound III (24.6 g, 100 mmol), oxalyl chloride (15.23 g, 120 mmol), and DMF (0.08 g, 1 mmol) were added to 246 g of dichloroethane and dissolved therein. The solution was heated at 60 C. and agitated for 12 hours. When the reaction was complete, the agitated solution was cooled down to room temperature. Then, a potassium hydroxide aqueous solution was added to the cooled product for neutralization. Then, an organic layer was separated and concentrated, obtaining 22.7 g of a compound IV (85.8% of a yield).
	With thionyl chloride; In dichloromethane; for 3h;Inert atmosphere; Reflux;	A mixture of <strong>[19694-02-1]1-pyrenecarboxylic acid</strong> (0.492g, 2.0 mmol) and thionyl chloride (3mL, 41.0 mmol) 20 mL dichloromethane was refluxed for 3 hr under argon atmosphere. The reaction mixture was distilled to remove excess thionyl chloride and dichlormethane to afford the compound 4 as a white solid, which was used for the next reaction without further purification. To a solution of unpurified 4 in 20 mL of dichloromethane was added 1,2-ethanedithiol(0.084 mL, 1.0 mmol) and solution was refluxed for 1 hr under argon protection. After the reaction mixture was cooled down to room temperature, dichloromethane was removed by rotary evaporation to give the crude product that was purified by column chromatography (silica, 220-400 mesh, hexane:EtOAc = 2:1 v/v). The product is isolated as a pale powder LFS-2 (0.43g, 79%). 1H NMR (300 MHz, DMSO) delta: 1.22 (m, 4H), 8.15 (t, 2H, J=7.5), 8.18-8.42 (m, 12H), 8.58(d, 2H, J=7.4), 9.23 (d, 2H, J=8.4); 13C (75MHz, DMSO) delta: 28.1, 124.0, 124.5, 124.9, 125.7, 126.3, 126.5, 126.9, 127.8, 128.7, 128.9, 129.3, 130.1, 130.4, 131.2, 133.4, 171.5. MS: m/z (MH)+ 550.18. Anal. calcd for C36H22O2S2: C, 78.52; H, 4.03. Found: C, 78.34; H, 4.09.
	With oxalyl dichloride; at 20℃; for 24h;Inert atmosphere;	<strong>[19694-02-1]Pyrene-1-carboxylic acid</strong> (0.5g, 2.0mmol), was dissolved in oxalyl chloride (5mL) at room temperature under N2. After stirring for 24h the oxalyl chloride was removed in vacuo to leave a pale yellow solid. Benzene (10mL×2) was added and distilled in vacuo to remove residual oxalyl chloride. The resulting solid was dissolved in 20mL of benzene, treated with trimethylsilylazide (1mL) and refluxed for 24h. At the end of this time the solvent was removed in vacuo to afford 1-pyrenyl isocyanate 13 (85% yield).

	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 3h;	To a solution of <strong>[19694-02-1]1-pyrenecarboxylic acid</strong> (0.25 g,1.0 mmol) in CH2Cl2 (20 mL), were added oxalyl chloride (0.38 g, 3.0 mmol) and 2 drops of DMF. After stirring for 3 hat room temperature, the solvent was removed under reduced pressure. The resulting solid was dissolved in CH2Cl2 (20 mL), and then TEA (2.0 g, 20 mmol) and 1-(methylthio)ethylamine (0.14 g, 1.5 mmol) were added. After stirring for 1 h at room temperature, the solvent was removed under reduced pressure. The product was purified by silica gel chromatography with EA:Hex (1:1) as eluent. The solid product was recrystallized from MeOH to give a white solid (0.20 g, 63%).
	With thionyl chloride; In dichloromethane; at 60℃; for 3h;Inert atmosphere;	A solution of 2 mmol (492 mg) pyrenecarboxylic acid in 5 mL of CH2Cl2 was added to a solution of thionyl chloride 30 mmol (3 mL) by dropwise and stirred at 60 C under argon atmosphere for about 3 hours. After the reaction was completed, the solvent was removed in vacuo and 2.0 mmol (250 mg) of 1-3-(aminopropyl)imidazole was added to the residue remaining in 10 mL of dry CH2Cl2 at room temperature, And the mixture was stirred at 70 for 5 hours under argon atmosphere. After the reaction was completed, the reaction mixture was concentrated and purified by column chromatography using a 9: 1 by volume mixture of CH2Cl2 and methanol as eluent (Rf = 0.10) to give a white solid (yield 71%, 280 mg, mp: 151 C (CH2Cl2-hexane))
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 4h;	General procedure: 1-Pyrenecarboxylic acid (1.0 mmol, 0.25 g) (or 1-pyreneacetic acid (1.0 mmol, 0.26 g) or 1-pyrenebutyric acid (1.0 mmol, 0.29 g)) was dispersed in 10 mL of dichloromethane. Oxalyl chloride (3.0 mmol, 0.25 mL) and 1 drop of DMF as a catalyst were added to the reaction mixture. After stirring for 4 h at room temperature, the solution color turned orange. The solution was subjected to evaporation under reduced pressure and drying under vacuum to remove volatile residues. The resulting product was dissolved in dry dichloromethane and added slowly to a solution of N-hydroxysuccinimide (NHS) (2.0 mmol, 0.23 g) and triethylamine (3.0 mmol, 0.42 mL) in dichloromethane. After stirring for 1 h, the solution was washed with distilled water and the organic layer was separated. The solvent was removed under reduced pressure and the precipitate was purified by recrystallization (CH2Cl2/CH3OH)
	With thionyl chloride; at 70℃; for 2h;Inert atmosphere;	Weigh 1.0g (about 0.004mol) Preparation of pyrene formic acid from the previous step,Dissolved in 5.0ml of SOCl2,Under a nitrogen atmosphere at 70 reflux 2h.After the reaction is completed,Spin the solvent,And dried in vacuo.The newly prepared pyrene formyl chloride was dissolved in methylene chloride,Then slowly added dropwise to a solution of 1.5g of diethanolamine dissolved in CH2Cl2,Stir at room temperature for 2h.After stopping the reaction,Washed three times with deionized water,Liquid separation,The organic layer was spun dry and dried in vacuo.The resulting crude product was developed with ethyl acetate: methanol = 10: 1,Silica gel column chromatography separation and purification,Finally, 0.86 g (about 0.0029 mol) of pale yellow solid,The yield is 72.5%.
		To a stirred CH2Cl2 (12 mL) solution of <strong>[19694-02-1]1-pyrenecarboxylic acid</strong> (0.429 g, 2 mmol) was added DMF (few drops) at 0C, and the resulting solution was stirred for 5 min. To the solution was slowly added SOCl2 (0.288 g, 2.4 mmol) at 0 C, and the resulting solution was stirred at room temperature for 24 h and concentrated in vacuo to give 1-pyrenecarbonyl chloride, which was used for the further reaction without purification. To a stirred suspension of NaH (0.120 g, 5 mmol) in THF (15 mL) was slowly added THF (10 mL) solution of PhOH (0.094 g, 1 mmol), and the resulting solution was stirred at room temperature for 10 min. To the solution was added THF (10 mL) solution of 1-pyrenecarbonyl chloride, and the resulting solution was stirred at room temperature for 1 h, then concentrated in vacuo. To the residue was added satd NaHCO3 (10 mL). The mixture was extracted with CH2Cl2 (10 mL x 3). The combined organic layers were washed with brine (20 mL), separated, dried over MgSO4, filtered, and concentrated in vacuo. Reprecipitation from CH2Cl2/hexane gave phenyl 1-pyrenecarboxylate (4, 0.137g, 39% yield) as yellow solids. 1H NMR (400 MHz, CDCl3) d 7.31-7.39 (m, 3H), 7.51 (t, J = 8.0 Hz, 2H), 8.05-8.13 (m, 2H), 8.19-8.30 (m, 5H), 8.89 (d, J = 8.0 Hz, 1H), 9.38 (d, J = 9.2 Hz, 1H) ppm; 13C NMR (100 MHz, CDCl3) d 122.0, 122.1, 124.1, 124.2, 124.8, 124.9, 125.9, 126.4, 126.5, 126.6, 127.1, 129.0, 129.6, 129.9, 130.1, 130.3, 131.0, 131.9, 134.9, 151.1, 166.3 ppm
	With thionyl chloride; In dichloromethane; at 40℃; for 7h;	2) 0.2 g of pyrenecarboxylic acid was dissolved in 20 ml of dichloromethane. 1.0 ml of thionyl chloride was slowly added dropwise, and the mixture was heated under reflux at 40 C for 7 h. After the reaction is completed, the solvent is evaporated under reduced pressure to give pyrenoyl chloride;
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 4h;	[00166] To a solution of <strong>[19694-02-1]1-pyrenecarboxylic acid</strong> (50 mg, 0.2 mmol) in DCM (2 ml_) was added oxalyl chloride (51.5 muIota_, 0.6 mmol). One drop of DMF was also injected as a catalyst. The resulting mixture was stirred at room temperature for 4 h. Evaporation of the volatiles yielded pyrene-1-carbonyl chloride. The product was dissolved in DCM (1 ml_) and was added dropwise to the solution of DPA (183 muIota_, 1.02 mmol) in DCM (2.5 ml_). The resulting solution was stirred at room temperature for 3 h. The reaction mixture was washed with distilled water, evaporated, and concentrated to dryness to afford the product as a yellowish oil. 1H NMR (400 MHz, DMSO-de) delta 8.72 (dt, J = 5, 1.5 Hz, 1H), 8.54 - 8.48 (m, 1H), 8.44 - 8.02 (m, 9H), 7.90 (td, J = 8, 2 Hz, 1H), 7.65 (td, J = 8, 2 Hz, 1H), 7.57 (d, J = 8 Hz, 1H), 7.41 (ddd, J = 8, 5, 1Hz, 1H), 7.24 (ddd, J = 8, 5, 1Hz, 1H), 7.11 (d, J = 8 Hz, 1H), 5.24 (s, 1H), 4.74 (s, 1H), 4.51 (d, J = 14 Hz, 2H).13C NMR (100 MHz, DMSO-de) delta 171.41, 157.38, 156.58, 149.77, 149.75, 137.43, 137.25, 131.81, 131.41, 131.17, 130.78, 128.80, 128.51, 127.64, 127.44, 127.11, 126.25, 126.08, 125.05, 124.89, 124.47, 124.12, 124.08, 123.03, 122.98, 122.71, 122.20, 54.48, 50.33. LRMS (ESI+) m/z calc'd for NsONa [M + Na]+ 450.50, found 450.41.
	With thionyl chloride; In dichloromethane; at 40℃; for 7h;	1-Pyrenecarboxylic acid (0.25 g, 1.0 mmol) was dissolved in 15.0 mLdichloromethane, followed by the addition of SOCl2 (1.0 mL). Theresulting mixture was stirred at 40 C for 7 h under the monitoring ofTLC. After the reaction, the solvent was removed under vacuum and thecrude product (pyrene-1-carbonyl chloride) was ready for next step.

Reference： [1]Magnetic Resonance in Chemistry,1999,vol. 37,p. 163 - 165
[2]Tetrahedron,2006,vol. 62,p. 11687 - 11696
[3]Patent: US2014/186777,2014,A1 .Location in patent: Paragraph 0080
[4]Magnetic Resonance in Chemistry,1985,vol. 23,p. 150 - 155
[5]Journal of Medicinal Chemistry,1995,vol. 38,p. 3094 - 3105
[6]Journal of Organic Chemistry,1996,vol. 61,p. 9494 - 9502
[7]Analytical Chemistry,1997,vol. 69,p. 1262 - 1264
[8]Chemical and Pharmaceutical Bulletin,1999,vol. 47,p. 151 - 155
[9]Organic Letters,2004,vol. 6,p. 1489 - 1492
[10]Journal of the American Chemical Society,2007,vol. 129,p. 347 - 354
[11]Chemistry - A European Journal,2003,vol. 9,p. 1922 - 1932
[12]Journal of the American Chemical Society,2007,vol. 129,p. 3818 - 3819
[13]Journal of Organic Chemistry,2007,vol. 72,p. 7939 - 7946
[14]Chemical Communications,2010,vol. 46,p. 6989 - 6991
[15]Organic Letters,2011,vol. 13,p. 370 - 373
[16]Dalton Transactions,2010,vol. 39,p. 7250 - 7261
[17]Tetrahedron Letters,2011,vol. 52,p. 2692 - 2696
[18]Chemical Communications,2011,vol. 47,p. 8796 - 8798
[19]Tetrahedron Letters,2011,vol. 52,p. 4843 - 4847
[20]Journal of Chemical Sciences,2011,vol. 123,p. 773 - 781
[21]Inorganic Chemistry,2012,vol. 51,p. 1634 - 1639
[22]Chemistry - A European Journal,2012,vol. 18,p. 4782 - 4790
[23]Journal of Organic Chemistry,2012,vol. 77,p. 3986 - 3996
[24]Chemical Communications,2012,vol. 48,p. 11193 - 11195
[25]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5748 - 5753
[26]Journal of Materials Chemistry,2012,vol. 22,p. 675 - 683
[27]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 2189 - 2192
[28]Journal of the American Chemical Society,2014,vol. 136,p. 12201 - 12204
[29]Supramolecular Chemistry,2014,vol. 26,p. 141 - 150
[30]Organic and Biomolecular Chemistry,2015,vol. 13,p. 7736 - 7749
[31]European Journal of Organic Chemistry,2016,vol. 2016,p. 343 - 356
[32]Patent: KR101521756,2015,B1 .Location in patent: Paragraph 0053; 0063; 0064
[33]Chemistry - A European Journal,2017,vol. 23,p. 6490 - 6494
[34]Tetrahedron Letters,2017,vol. 58,p. 2927 - 2930
[35]Chemical Communications,2017,vol. 53,p. 5190 - 5192
[36]Patent: CN107286038,2017,A .Location in patent: Paragraph 0060; 0062
[37]Tetrahedron Letters,2017,vol. 58,p. 4377 - 4380
[38]Patent: CN105085404,2017,B .Location in patent: Paragraph 0056; 0059; 0063
[39]Patent: WO2019/68177,2019,A1 .Location in patent: Paragraph 00166
[40]MedChemComm,2019,vol. 10,p. 1173 - 1176
[41]Dyes and Pigments,2020,vol. 174
[42]Journal of Physical Organic Chemistry,2020,vol. 33

4
[ 6066-82-6 ]
[ 19694-02-1 ]
[ 204705-13-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 20℃;	N,N'-Dicyclohexylcarbodiimide (DCC, 0.854g, 4.14mmol) was added to a solution of <strong>[19694-02-1]1-pyrenecarboxylic acid</strong> (1.71g, 3.94mmol) and N-hydroxysuccinimide (HOSu, 0.476g, 4.14mmol) in anhydrous THF (10mL) at 0C. The reaction mixture was warmed to room temperature and stirred overnight. The white precipitate was filtered off and the filtrate was dried in vacuo. The resulting activated ester was added to a solution of N-Boc ornithine (0.854g, 4.14mmol) and N,N-diisopropylethylamine (DIPEA, 4.1mL, 23.6mmol) in anhydrous DMF (10mL). The reaction mixture was stirred under N2 for 24h at 70C. The mixture was diluted with CH2Cl2. The organic phase was washed with 0.5N HCl, brine, dried over MgSO4, and concentrated in vacuo. After the solvent was removed in vacuo, the residue was purified by column chromatography over silica gel using 7:1 CH2Cl2/MeOH as the eluent to give a light yellow powder (1.3g, 72%).
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; for 2h;	To a solution of <strong>[19694-02-1]1-pyrenecarboxylic acid</strong> (65 mg, 0.24 mmol) in DCM/DMF (2 mL each)was added N-hydroxysuccinimide (34 mg, 0.29 mmol) and EDC.HC1 (70 mg, 0.36mmol). The reaction was stirred for 2h and subsequent diluted with DCM (10 mL), washed with aqueous citric acid (10%, 5 mL) and saturated NaHCO3 (3 x 5 mL), dried over Na2504, filtrated and concentrated in vacuo to give crude 45.

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 16097 - 16100
Angew. Chem.,2019,vol. 131,p. 16243 - 16246,4
[2]Tetrahedron Letters,1998,vol. 39,p. 1321 - 1324
[3]Tetrahedron,2013,vol. 69,p. 6051 - 6059
[4]Patent: WO2016/53107,2016,A1 .Location in patent: Page/Page column 97
[5]Chemistry - A European Journal,2018,vol. 24,p. 12638 - 12651

5
[ 19694-02-1 ]
[ 29390-67-8 ]
6-deoxy-6-(pyrene-1-carboxamido)-β-cyclodextrin [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 7071 - 7076

6
[ 19694-02-1 ]
[ 688008-52-8 ]
[ 688008-56-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 4h;	A2. (S)-4- [ (E)- (R)-1- (2-CHLORO-ACETOXY)-13- (PYRENE-1-CARBONYLOXY)-TRIDEC-2-ENYL]-2, 2- dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester A solution of 540 mg of (S)-4-[(E)-(R)-1-(2-CHLORO-ACETOXY)-13-HYDROXY-TRIDEC-2-ENYL]-2, 2- dimethyl-oxazolidine-3-carboxylic acid ter-butyl ester (prepared analogously as described in: KOZIKOWSKI et AL., Tetrahedron Lett. 1996,37, 3279-3282) in 10 ml of dry CH2CI2 is treated with 271 mg of PYRENE-1-CARBOXYLIC acid, 422.4 mg of 1- (3-DIMETHYLAMINOPROPYL)-3-ETHYL- carbodiimide HCI and 269.3 mg of DMAP and stirred for 4 hours at RT. The reaction mixture obtained is distributed between EtAc and 1 N aq. HCI. The organic layer obtained is washed with sat. aq. NAHCO3 solution and brine, dried and solvent is evaporated. P (S)-4-[(E)-(R)-1-(2-CHLORO-ACETOXY)-13-(PYRENE-1-CARBONYLOXY)-TRIDEC-2-ENYL]-2, 2-DIMETHYL- oxazolidine-3-carboxylic acid tert-butyl ester is obtained.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1555 - 1558
[2]Patent: WO2005/30780,2005,A1 .Location in patent: Page/Page column 30

7
[ 19694-02-1 ]
[ 745796-05-8 ]
[ 745796-06-9 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 8364 - 8365

8
[ 19694-02-1 ]
[ 745796-00-3 ]
[ 745796-01-4 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 8364 - 8365

9
[ 19694-02-1 ]
[ 745795-95-3 ]
[ 745795-96-4 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 8364 - 8365

10
[ 19694-02-1 ]
[ 2450-71-7 ]
[ 500783-43-7 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 4820 - 4827
[2]Carbohydrate Research,2006,vol. 341,p. 35 - 40
[3]Langmuir,2010,vol. 26,p. 13168 - 13172
[4]Tetrahedron,2004,vol. 60,p. 7267 - 7275
[5]Supramolecular Chemistry,2014,vol. 26,p. 141 - 150

11
[ 19694-02-1 ]
[ 799811-45-3 ]
[ 799811-49-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With N,N'-diethylcarbodiimide; In dichloromethane; at 20℃; for 3h;	Nucleoside 5 (300 mg, 0.39 MMOL) was dissolved in anhydrous dichloromethane (6 CM3), and to the stirred mixture at rt was added <strong>[19694-02-1]1-pyrenecarboxylic acid</strong> (170 mg, 0.59 mmol) AND N, N-DIETHYLCARBODIIMIDE (120 mg, 1.22 MMOL). After 3 hours, DICHLOROMETHANE (50 cm3) was added followed by washing using a saturated aqueous solution of NaHCO3 (3 x 20 CM3). The organic phase was dried (Na2SO4) and evaporated to dryness under reduced pressure. The residue was purified twice by silica gel column chromatography using DCM and pyridine (0.5% pyridine in DICHLOROMETHANE (v/v) ) as ELUENT YIELDING NUCLEOSIDE 6b (288 mg, 0.29 mmol, 75%) as a white solid material. 13C NMR (CDCl3) D 169.679, 163.63, 158.67, 150.20, 150.13, 149.74, 144.23, 135.49, 135.39, 135.34, 131.57, 131.16, 130.95, 130.11, 130.05, 128.74, 128.65, 128.21, 128.14, 127.88, 127.38, 127.12, 126.28, 125.68, 125.57, 124.71, 124.62, 124.54, 124.46, 123.92, 123.79, 123.68, 113.13, 110.94, 110.87, 89.37, 86.79, 83.98, 83.91, 72. 29, 72.11, 64.20, 64.10, 58.88, 58.80, 55.20, 54.89, 54.78, 54.69, 47.58, 42.25, 41.08, 25.67, 17.92, 11.70,-4. 59, -5. 12. MALDI-HRMS M/Z 1007.4420 ( [M + Na] +, C59H64N40SSI-NA ) ; calc. 1007.43856.

Reference： [1]Chemical Communications,2004,p. 1064 - 1065
[2]Patent: WO2004/106356,2004,A1 .Location in patent: Page 29

12
[ 866611-96-3 ]
[ 19694-02-1 ]
[ 1061578-75-3 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 1070 - 1081
[2]Nucleosides, nucleotides and nucleic acids,2007,vol. 26,p. 1403 - 1405

13
[ 19694-02-1 ]
[ 128625-52-5 ]
C₂₃H₁₃N₃O₂ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 198 - 209

14
[ 129-00-0 ]
[ 124-38-9 ]
[ 19694-02-1 ]

Reference： [1]Chemistry Letters,2012,vol. 41,p. 913 - 914,2

15
[ 894423-93-9 ]
[ 19694-02-1 ]
[ 1426075-65-1 ]

Yield	Reaction Conditions	Operation in experiment
21%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 24.0833h;Inert atmosphere;	Diol (10) (230, 1.6 mM), <strong>[19694-02-1]1-pyrenecarboxylic acid</strong> (1.009 g, 4.1 mM) and DMAP (19.5 mg, 0.16 mM) were dissolved in dry DCM (20 mL) under a nitrogen atmosphere. The mixture was then cooled to 0 C before DCC (700 mg, 3.4 mM) was added, which was stirred for 5 min at 0 C and 24 h at 20 C. Completion of the reaction was monitored by TLC (ethyl acetate/hexane, 1:1) Rf 0.28. Filtration of the reaction removed any precipitated dicyclohexylurea, then the filtrate was evaporated in vacuo. The residue was dissolved in DCM, washed twice with 0.5 N HCl and saturated NaHCO3, then dried over MgSO4. The organic layer was subsequently concentrated under vacuum and the residue was purified via flash column chromatography (ethyl acetate/hexane 1:3) to yield ( 9) 202 mg (21%) as a brown solid. Mp 178-180 C. IR numax/cm-1: 1249 (C-O str), 1595 (N=N cis str), 1701 (C=O str). 1H NMR (CDCl3) deltaH 9.16 (2H, d, 3J1?-2? 9.4 Hz, H-1?), 8.49 (2H, d, 3J9?-8? 8.9 Hz, H-9?), 8.19 (2H, d, 3J2?-1? 9.4 Hz, H-2?), 8.10 (2H, d, 3J8?-9? 8.9 Hz, H-8?), 7.95-7.88 (6H, m, H-3?, 4?, 7), 7.82 (2H, d, 3J6?-5? 8.7 Hz, H-6?), 7.63 (2H, d, 3J5?-6? 8.7 Hz, H-5?), 5.73 (2H, t, 3J2-1/3eq, 4-3eq/5 5.5 Hz, H-2/4), 5.64 (2H, t, 3J1-2/8eq, 5-4/8eq 6.0 Hz, H-1/5), 2.89 (1H, d, 2J8ax-8eq 12.6 Hz, H-8ax), 2.31 (1H, d, 2J3eq-3ax 17.1 Hz, H-3eq), 2.01 (1H, dt, 3J3ax-2/4 5.5 Hz, 2J3ax-3eq 17.1 Hz, H-3ax), 1.67 (1H, dt, 3J8eq-1/5 6.0 Hz, 2J8eq-8ax 12.6 Hz, H-8eq). 13C NMR deltaC 166.4 (C=O), 134.4, 131.3, 130.9, 130.1, 129.9, 129.8, 128.4, 126.9, 126.5, 126.3, 126.3, 124.7, 124.4, 123.9, 123.8, 122.6 (Pyr-C), 81.6 (C-2/4), 63.4 (C-1/5), 33.9 (C-3), 24.9 (C-6). MS (APCI) m/z [M+NH4]+ 598.2. Elemental analysis calcd for C40H26N2O4: C, 80.25; H, 4.38; N, 4.68. Found: C, 79.97; H, 4.14; N, 4.42%.

Reference： [1]Tetrahedron,2013,vol. 69,p. 2758 - 2766

16
[ 894423-93-9 ]
[ 19694-02-1 ]
2-pyrenoyl-6,7-diazabicyclo[3.2.1]oct-6-ene-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%		Diol (10) (50 mg, 0.35 mM), DCC (77 mg, 0.37 mM) and a catalytic amount of DMAP (2 mg, 0.016 mM) was dissolved in dry DCM (10 mL). This mixture was then cooled to 0 C. Separately, <strong>[19694-02-1]1-pyrenecarboxylic acid</strong> (111 mg, 0.45 mM) was dissolved dry DCM (10 mL). Both mixtures were kept under an inert nitrogen atmosphere and left to stir for 10 min. 1 mL of the pyrene solution was added every 5 min to the diol solution. After 45 min, the addition was complete and the mixture was left to stir in the dark for 24 h. Completion of the reaction was monitored by TLC (ethyl acetate/hexane, 1:1) Rf 0.15. Filtration of the reaction mass was carried out to remove any precipitated dicyclohexylurea, then the filtrate was evaporated in vacuo. The residue was dissolved in DCM, washed twice with 0.5 N HCl and saturated NaHCO3, and then dried over MgSO4. Evaporation of solvent and flash column chromatography (ethyl acetate/hexane, 1:1) yielded 32 mg (28%) of a brown solid ( 15). Mp 102-106 C. IR numax/cm-1: 1593 (N=N str cis), 1711 (C=O str), 3270 (OH str). 1H NMR (CDCl3) deltaH 9.30 (1H, d, 3J1?-2? 9.5 Hz, H-1?), 8.65 (1H, d, 3J9?-8? 8.9 Hz, H-9?), 8.16-8.09 (6H, m, H-2?/3?/4?/6?/7?/8?), 8.07 (1H, d, 3J5?-6? 8.4 Hz, H-5?), 5.54-5.47 (2H, m, H-2/4), 5.35-5.31 (1H, m, H-1), 4.27-4.25 (1H, m, H-5), 2,76 (1H, d, 2J3eq-3ax 12.55 Hz, H-3eq), 2.00 (1H, br s, H-OH), 1.93-1.83 (1H, m, H-8ax/8eq), 1.57-1.51 (1H, m, H-3ax). 13C NMR deltaC 166.8 (C=O), 134.7, 131.4, 131.0, 130.4, 129.9, 129.8, 128.4, 127.2, 126.5, 126.5, 126.4, 124.9, 124.7, 124.2, 124.1, 122.4 (Pyr-C), 84.4 (C-4), 81.3 (C-2), 63.8 (C-1), 60.6 (C-5), 33.2 (C-3), 24.4 (C-6). MS (APCI) m/z [M+NH4]+ 371.23. Elemental analysis calcd for C23H18N2O3: C, 74.58; H, 4.90; N, 7.56. Found: C, 74.43; H, 4.61; N, 7.23%.

Reference： [1]Tetrahedron,2013,vol. 69,p. 2758 - 2766

17
[ 14533-84-7 ]
[ 19694-02-1 ]
pentafluorophenyl pyrene-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In dichloromethane; at 20℃; for 1h;	Procedure for the preparation of compound 34, shown below. Triethylamine (0.616 g, 6.09 mmol) was added to a solution of <strong>[19694-02-1]1-pyrenecarboxylic acid</strong> (1.0 g, 4.06 mmol) in dry DCM (20 ml) followed by pentafluorophenyl trifluoroacetate (1.251 g, 4.47 mmol). The reaction was kept at room temperature for 1 h, concentrated in vacuo and then diluted with MeOH. The resultant solid material was isolated by filtration, washed with MeOH and dried in vacuo to give the PFP 1-pyrenecarboxylate (1.50 g, 3.64 mmol, yield=90%) as yellow fluffy solid. A portion of the PFP 1-pyrenecarboxylate (1.38 g, 3.35 mmol) was added to a mixture of compound 25 (2.79 mmol) and triethylamine (0.847 g, 8.37 mmol) in dry DCM (20 ml). The suspension was stirred under argon at room temperature overnight, then diluted with 10% citric acid and extracted with DCM. The organic solution was separated, washed with saturated aqueous NaHCO3, saturated aqueous NaCl, dried over MgSO4, filtered from drying agent, and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, 0-20% acetone in EtOAc) to give product 34 (1.78 g, 2.09 mmol, 75%) as white solid. 1H NMR (DMSO-d6): delta 12.43 (s, 1H), 8.94 (t, J=5.7 Hz, 1H), 8.56 (d. J=9.0 Hz, 1H). 8.36-8.08 (m, 9H), 7.31-7.13 (m, 9H), 6.78-6.73 (m, 4H), 6.54 (dd, J=7.0; 4.0 Hz, 1H), 5.36 (d, J=-4.8 Hz, 1H). 4.52 (qn, J=5.3 Hz, 1H), 3.93 (dd, J=9.5: 5.5 Hz, 1H), 3.70-3.60 (m, 8H), 3.12-2.99 (m, 2H), 2.92 (t, J=7.0 Hz, 2H), 2.81-2.74 (m, 1H), 2.36-2.27 (m, 1H).

Reference： [1]Patent: US2013/261014,2013,A1 .Location in patent: Paragraph 0180-0181

18
[ 19694-02-1 ]
[ 106-96-7 ]
prop-2-yn-1-yl pyrene-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93.5%	With potassium carbonate; In N,N-dimethyl-formamide; at 105℃; for 7h;	232.5 mg of 1-pyrene formic acid (0.938 mmol)Was dissolved in 2.4 mL of N, N-dimethylformamide,276 mg of 3-bromopropyne (2.35 mmol) and 472 mg of potassium carbonate (3.28 mmol)The reaction temperature was controlled at 105 C and the reaction was stirred for 7 hours.Cooled to room temperature, 25 mL of deionized water was added, extracted with 125 mL of ethyl acetate,The organic phase was collected and the organic phase was washed with brine (50 g / L), dried over 125 mg of anhydrous sodium sulfate,Filtration; rotary evaporation to remove the organic solvent,The resulting solid was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane, V / V = 4: 1)To give 1-prolyl 1-pyrene formate as a white solid (yield 93.5%).

Reference： [1]Patent: CN106632101,2017,A .Location in patent: Paragraph 0037; 0042; 0047; 0048
[2]Chemistry - A European Journal,2014,vol. 20,p. 11699 - 11702,4

19
[ 19694-02-1 ]
C₄₈H₅₄N₆O₄ [ No CAS ]
C₆₅H₆₂N₆O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at -15 - 25℃; for 48h;	(1-4) To the system prepared in step 1-3 was added 5mL solvent N,N-dimethylformamide (DMF) and 0.35g <strong>[19694-02-1]1-pyrenecarboxylic acid</strong>. At -15C, to this was added dropwise with stirring 0.3g DCC, 0.05g DMAP, and 0.07g HOBt in dichloromethane solution. Reacted at room temperature (25C) for 48 hours. (1-5) The system from step 1-4 was evaporated under reduced pressure to remove solvent. Product was purified by silica gel column chromatography, eluent ethyl acetate:petroleum ether = 2:1, to give compound PHE-2.

Reference： [1]Journal of Materials Chemistry C,2015,vol. 3,p. 3399 - 3405
[2]Patent: CN105837587,2016,A .Location in patent: Paragraph 0139; 0187; 0188

20
[ 19694-02-1 ]
C₇₅H₈₁N₉O₇ [ No CAS ]
C₉₂H₈₉N₉O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at -15 - 25℃;	(2-5) To the system prepared in step 2-4 was added 5mL solvent N,N-dimethylformamide (DMF) and 0.20g <strong>[19694-02-1]1-pyrenecarboxylic acid</strong>. At -15C, to this was added dropwise with stirring 0.20g DCC, 0.05g DMAP, and 0.03g HOBt in dichloromethane solution. Reacted at room temperature (25C) for 72 hours. (2-6) The system from step 2-5 was evaporated under reduced pressure to remove solvent. Product was purified by silica gel column chromatography, eluent ethyl acetate, to give compound PHE-5.

Reference： [1]Journal of Materials Chemistry C,2015,vol. 3,p. 3399 - 3405
[2]Patent: CN105837587,2016,A .Location in patent: Paragraph 0142; 0196; 0197

21
[ 89-73-6 ]
calcium perchlorate tetrahydrate [ No CAS ]
manganese(II) perchlorate hexahydrate [ No CAS ]
[ 75-09-2 ]
[ 19694-02-1 ]
[ 121-44-8 ]
(NHEt₃)₂[Mn₄Ca(1-pyrenecarboxylato)₄(salicylhydroxime-H₃)₄]*5(CH₂Cl₂) [ No CAS ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 2137 - 2151

22
[ 172646-07-0 ]
[ 19694-02-1 ]
dimethyl 2,2'-((2-(2-(2-(bis(2-methoxy-2-oxoethyl)amino)-5-(pyrene-1-carboxamido)phenoxy)ethoxy)phenyl)azanediyl)diacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		A solution of 1-Pyrene carboxylic acid (42 mg, 0.17 mmol) in 4 ml_ DMF was incubated with TBTU (108 mg, 0.34 mmol) and DIPEA (88 muIota_, 0.51 mmol) for 20 min. Following incubation, compound 19 (92 mg, 0.17 mmol) was added. The reaction mixture was stirred at rt for 24 h under N2 atmosphere. The reaction mixture was extracted with EtOAc washing 3 times with saturated NaHC03(aq) and purified by silica gel column chromatography using 1 :19 MeOH:DCM eluent to yield dimethyl 2,2'-((2-(2-(2-(bis(2- methoxy-2-oxoethyl)amino)-5-(pyrene-1 - carboxamido)phenoxy)ethoxy)phenyl)azanediyl)diacetate as a white solid (85mg, 65%). 1H NMR (400 MHz, CDCI3) delta 8.55 (s, 1 H), 8.45 (d, J = 9.2 Hz, 1 H), 8.13 (t, J = 7.7 Hz, 2H), 8.01 - 7.94 (m, 4H), 7.88 (d, J = 9.0 Hz, 1 H), 7.50 (s, 1 H), 7.32 (d, J = 8.5 Hz, 1 H), 6.93 - 6.72 (m, 5H), 4.27 (s, 2H), 4.19 (s, 2H), 4.16 - 4.06 (m, 9H), 3.55 (s, 6H), 3.47 (s, 6H); 3C NMR (100 MHz, CDCI3) delta 171 .8, 171.7, 150.5, 150.3, 138.9, 135.8, 133.6, 132.3, 130.9, 130.8, 130.4, 128.5, 128.45, 128.36, 127.6, 126.8, 126.1 , 125.7, 125.6, 124.45, 124.36, 124.0, 123.9, 122.3, 121 .2, 1 19.2, 119.1 , 113.7, 112.9, 1 12.8, 106.5, 67.4, 66.8, 53.3, 53.1 , 51 .5, 51.4.

Reference： [1]Patent: WO2015/89639,2015,A1 .Location in patent: Paragraph 00207; 00208

23
[ 1606-67-3 ]
[ 19694-02-1 ]
[ 78751-44-7 ]

Yield	Reaction Conditions	Operation in experiment
80%		To a two-neck round-bottom flask (100 mL) were added <strong>[19694-02-1]1-pyrenecarboxylic acid</strong> (105 mg, 0.426mmol), toluene (20 mL), triethylamine (100 L, 0.72mmol), and diphenylphosphorylazide (250 L, 1.0mmol). After the mixture had been stirred for 30min at 80 C, 1-aminopyrene (40 mg, 0.184mmol) in THF (10 mL) was added, and the mixture was refluxed for 15 h. The solvent was filtered by suction filtration and the residue was washed with methanol a number of times. The product was recrystallized from DMF H2Oand washed with MeOH to give a light yellow solid (84 mg, 80%). 1HNMR (DMSO-d6, 400 MHz): delta 8.08 (2H, t, J = 8.8 Hz), 8.10 (2H, d,J = 8.93 Hz), 8.16 (2H, d, J = 8.93 Hz), 8.26 (6H, d, J = 8.4 Hz), 8.33 (2H, d, J = 8.6 Hz), 8.54 (2H, d, J = 8.47 Hz), 8.75(2H, d, J = 8.36 Hz), 9.75 (2H, s). 13 C NMR (DMSO-d6, 400MHz): delta 154.1, 133.7, 133.6, 131.8, 131.1, 127.7, 127.5, 127.1,126.7, 126.2, 125.9, 125.5, 125.1, 125.0, 124.7, 121.7, 120.7.Anal. calcd. for C33H20N2O: C, 86.07; H, 4.38; N, 6.08; O,3.47%. Found: C, 85.86; H, 4.63; N, 6.06; O, 3.45%.

Reference： [1]Bulletin of the Chemical Society of Japan,2015,vol. 88,p. 1100 - 1104

24
[ 13781-67-4 ]
[ 19694-02-1 ]
2-(thiophen-3-yl)ethyl pyrene-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 12.5h;Inert atmosphere;	General procedure: General SynthesisThe appropriate thiophene alcohol (0.82 mmol), the selected carboxylic acid (1.23 mmol), DCC(2.46 mmol) and DMAP (2.05 mmol) were dissolved in CH2Cl2 (15 mL) at 0 C for 30 min. The resultingmixture was stirred at room temperature for 12 h under inert atmosphere. The suspension was filteredin order to remove DCU formed during the reaction, and the filtrates were concentrated under reducedpressure at 45 C. The crude product was purified by column chromatography in silica gel, usingn-hexane/CH2Cl2 (2:5) and then pure CH2Cl2 as eluent to give the desired product TPM1 (Figure 1).All monomers were characterized by 1H- and 13C-NMR spectroscopy and the spectra are included inthe Supplementary Materials.2-(Thiophen-3-yl)ethylpyrene-1-carboxylate (TPM1): 3-Thiopheneethanol (0.105 g, 0.82 mmol),<strong>[19694-02-1]1-pyrenecarboxylic acid</strong> (0.302 g, 1.23 mmol), DCC (0.507 g, 2.46 mmol) and DMAP (0.250 mg,2.05 mmol). Light yellow powder. Yield: 87%. MS-CI: m/z = 356.0. 1H-NMR (CDCl3, ppm) (SchemeS1) delta: 7.85-9.2 (m, 9H, Py), 7.37 (dd, 1H, H5, J = 4.9, 3.0 Hz), 7.21 (d, 1H, H2, J = 4.7 Hz), 7.15 (dd, 1H,H4, J = 4.9, 1.3 Hz), 4.76 (t, 2H, J = 6.8 Hz), 3.26 (t, 2H, J = 6.8 Hz). 13C-NMR (CDCl3, ppm) (SchemeS1-1): 168.09 (C=O), 155.31 (C2, Thioph), 138.38 (C3, Thioph), 117.89 (C4, Thioph), 96.24 (C1, Thioph),134.41, 131.19, 131.09, 130.46, 129.72, 129.51, 128.47, 127.25, 126.40, 126.38, 126.27, 125.91, 124.98, 124.24,123.71, 121.94 (CPy), 65.23 (OCH2), 29.94 (CH2).

Reference： [1]Molecules,2016,vol. 21

25
[ 1589-47-5 ]
[ 19694-02-1 ]
C₂₁H₁₈O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; at 115℃; for 36h;Reflux;	EXAMPLE 2 To a 250 mL round bottomed flask containing a stir bar is added 100 g PGME (1.11 mol, 1.0 equiv) as a mixture of approximately 99.88% of 1-methoxypropan-2-ol (PM-2) and 0.12% of <strong>[1589-47-5]2-methoxypropan-1-ol</strong> (beta-isomer, PM-1). Benzoic anhydride (2.5 g, 11.1 mmol, 0.01 equiv) is next added to the flask, followed by concentrated sulfuric acid (10.9 g, 111.0 mmol, 0.1 equiv). A reflux condenser is affixed to the reaction and it is left to stir for 36 hours in an oil bath set to 115 C. At the end of this interval, the reflux condenser is removed and a vacuum-jacketed Vigreux column filled with glass beads 1 mm in diameter is attached. Atop this, a short path distillation head is placed with a 100 mL receiving flask. The temperature of the oil bath is increased to 130 C., and the first distillate fraction is collected as the major product, within a temperature range of 118-120 C. Analysis of this material indicates that it consists of starting material isomer PM-2 and is substantially free of isomer PM-1. This process is illustrated by the following reaction scheme. EXAMPLE 4 The procedure of Example 2 is repeated except that he benzoic anhydride is replaced with 1-pyrenecarboxylic acid (5.4 g, 22.2 mmol, 0.02 equiv), and the sulfuric acid catalyst is replaced with 12.1N aqueous hydrochloric acid (9.2 mL, 111.0 mmol, 0.1 equiv). Analysis of the distillate indicates that it is isomer PM-2 and is substantially free of isomer PM-1. This process is illustrated by the following reaction scheme.

Reference： [1]Patent: US2016/168064,2016,A1 .Location in patent: Paragraph 0016; 0018

26
[ 32089-54-6 ]
[ 19694-02-1 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(II) perchlorate hexahydrate; water; In acetonitrile; at 20℃; for 0.166667h;	To verify the Cu2+-induced hydrolysis of probe 1 to its carboxylic acid, 1H NMR and mass spectra of the signaling mixture of probe 1 and Cu2+ ions were obtained. Copper(II) perchlorate hexahydrate (0.06 g, 0.16 mmol) in distilled water (1.0 mL) was added to a solution of pyrenecarbohydrazide 1 (0.02 g, 0.08 mmol) in acetonitrile (9.0 mL). The mixture was stirred for 10 min at room temperature, extracted with dichloromethane, and then the solvent was evaporated. Because of the paramagnetic property of Cu2+ ions, the product was purified by passage through a short silica plug (CH2Cl2:CH3OH = 29:1, v/v) to remove Cu2+. The 1H NMR spectra of the obtained signaling product and 1-pyrenecarboxylic acid as a reference were recorded after protonation by adding one drop of trifluoroacetic acid. The signaling product was identified by 1H NMR and LRMS.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2927 - 2930

27
[ 1283594-41-1 ]
[ 19694-02-1 ]
N,N'-(((methylenebis(4,1-phenylene))bis(azanediyl))bis(2-oxoethane-2,1-diyl))bis(pyrene-1-carboxamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		Amixture of pyrene-1-carboxylic acid (270 mg, 1.1 mmol), hydroxybenzotriazole(HOBt, 162 mg, 1.2 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 230 mg, 1.2 mmol) wasdissolved in (CH2Cl2: DMF (1:1), 20 mL) solution and stirredvigorously at 0 C for 20 min under an argon atmosphere. Compound 5 (157 mg, 0.5 mmol) and diisopropylethylamine (DIPEA)(155 mg, 1.2 mmol) were added to the reaction mixture and subsequentlystirred at room temperature for another 8 h. Aftercompletion of the reaction (as detected via TLC analysis), the solventof the reaction mixture was removed under vacuum. Thecrude solid was dissolved in H2O and extracted with CH2Cl2, andthe organic layer was washed with H2O (2 x 50 mL) and a 5%aqueous NaCl solution (100 mL). The collected organic extract wasthen dried over anhydrous sodium sulfate and filtered. The filtratewas evaporated under reduced pressure, and the residue was purifiedby column chromatography using CH2Cl2:CH3OH (8:2) as theeluent to afford probe 1 as a white solid (325 mg, 85% yield);m.p. 302 C. 1H NMR (400 MHz, DMSO-d6): delta 3.91 (s, 2H, CH2),4.23 (d, J 6.0 Hz, 4H, 2 CH2), 7.22 (d, J 8.4 Hz, 4H, 4 ArH),7.61 (d, J 8.4 Hz, 4H, 4 ArH), 8.14 (t, J 8.0 Hz, 2H, 2 ArH),8.21e8.31 (m, 8H, 8 ArH), 8.36e8.38 (m, 6H, 6 ArH), 8.71 (d,J 9.2 Hz, 2H, 2 ArH), 9.03 (t, J 6.0 Hz, 2H, 2 PyCONH), 10.17(s, 2H, 2 ArNH); 13C NMR (100 MHz, DMSO-d6): delta 43.26, 119.30,123.62, 123.76, 124.42, 124.94, 125.34, 125.62, 125.79, 126.58,127.22, 127.92, 128.09, 128.33, 128.98, 130.23, 130.71, 131.59, 131.67,136.31, 137.03, 167.61, 169.41; HRMS (EI): calc'd. for C51H37N4O4(M + H+): 769.2809; found: m/z 769.2812.

Reference： [1]Dyes and Pigments,2017,vol. 147,p. 400 - 412

28
[ 19694-02-1 ]
[ 148627-63-8 ]
N-(2-((4-methoxyphenyl)amino)-2-oxoethyl)pyrene-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%		General procedure: Amixture of pyrene-1-carboxylic acid (270 mg, 1.1 mmol), hydroxybenzotriazole(HOBt, 162 mg, 1.2 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 230 mg, 1.2 mmol) wasdissolved in (CH2Cl2: DMF (1:1), 20 mL) solution and stirredvigorously at 0 C for 20 min under an argon atmosphere. Compound 5 (157 mg, 0.5 mmol) and diisopropylethylamine (DIPEA)(155 mg, 1.2 mmol) were added to the reaction mixture and subsequentlystirred at room temperature for another 8 h. Aftercompletion of the reaction (as detected via TLC analysis), the solventof the reaction mixture was removed under vacuum. Thecrude solid was dissolved in H2O and extracted with CH2Cl2, andthe organic layer was washed with H2O (2 x 50 mL) and a 5%aqueous NaCl solution (100 mL). The collected organic extract wasthen dried over anhydrous sodium sulfate and filtered. The filtratewas evaporated under reduced pressure, and the residue was purifiedby column chromatography using CH2Cl2:CH3OH (8:2) as theeluent to afford probe 1 as a white solid (325 mg, 85% yield);

Reference： [1]Dyes and Pigments,2017,vol. 147,p. 400 - 412

29
[ 1248386-96-0 ]
[ 19694-02-1 ]
N-(3,5-bis(pyridine-4-ylethynyl)phenyl)pyrene-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 72h;Schlenk technique; Inert atmosphere;	In a 10 mLSchlenk flask, 3,5-bis(pyridine-4-ylethynyl)aniline (100 mg, 0.34mmol), pyrene-1-carboxylic acid (118 mg, 0.48 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC.HCl) (72 mg, 0.38mmol), and catalytic amount (~10 mg) of 4-dimethylaminopyridine (DMAP) were added. After the flask was vacuumed and purged with N2and the process was repeated three times, freshly distilled 4 mL of CH2Cl2 was added using a syringe. The mixture was stirred at room temperature for 3 days, which led to a yellow precipitate. The yellow precipitate was collected and purified by column chromatography (CH2Cl2/methanol, 10:1) to afford ligand 4. Yield: 51 %; Mp. 185-186 C;1H NMR (CDCl3, 300 MHz): delta 8.65 (m, 5H),8.29 (d, J = 7.5 Hz, 2H), 8.25 (s, 2H), 8.20 (d, J = 7.5, 2H), 8.14-8.07 (m, 2H), 8.03 (d,J = 1.2 Hz, 2H ), 7.9 (s, 1H), 7.60 (t, J = 1.2 Hz, 1H), 7.41 (d,dJ = 5.7, 3 Hz, 4H).LRMS calculated for C37H22N3O [M+H]+ 524.18, found 524.3.

Reference： [1]Journal of Organometallic Chemistry,2017,vol. 847,p. 294 - 297

30
[ 112-43-6 ]
[ 19694-02-1 ]
C₂₈H₃₀O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 16h;Schlenk technique; Inert atmosphere;	Pyrene-carboxylic acid (1.1 g, 4.5 mmol), 10-undecen-1-ol (2.7 mL, 13 mmol),and dimethylaminopyridine (1.6 g, 13 mmol) were added to 50 ml of CH2Cl2. After stirring for 30min, N, N?-dicyclohexylcarbodiimide (1.0 g, 5.0 mmol) was added, and the reaction mixture wasstirred for 16 hours. The reaction mixture was filtered, and the solvent was removed in vacuo. Thecrude white powder was purified by column chromatography (SiO2 Hexane:EtOAc 98:2).Remaining solvents were removed in vacuo to provide a white powder (1.6 g, 4.0 mmol, 90%).1H NMR (700 MHz, DMSO) delta: 9.2 (1H, d, J=9.3); 8.7 (1H, d, J=8.1); 8.5 (2H, t, J=6.9); 8.5-8.4(3H, m); 8.4 (1H, d, J=7.4); 8.3 (1H, t, J=7.6); 5.9-5.8 (1H, m, J=4.5); 5.1 (1H, d, J=17.2); 5.0(1H, d, J=10.2); 4.6 (2H, t, J=6.5); 2.1 (2H, q, J=6.9); 1.9 (2H, quin, J=14.4); 1.6 (2H, quin,J=14.4); 1.5 (2H, quin, J=6.9); 1.4-1.3 (8H, m). 13C NMR (175 MHz, DMSO) delta: 167.7; 139.3;134.2; 131.1; 130.5; 130.3; 130.2; 129.9; 128.5; 127.7; 127.3; 127.2; 126.8; 125.0; 124.7; 124.4;124.1; 123.8; 115.1; 65.5; 33.6; 29.3; 29.2; 29.1; 28.9; 28.7; 28.6; 26.1. HRMS calculated for([C28H30O2] +H)+ 399.2246, observed 399.2317.

Reference： [1]Chem,2018,vol. 4,p. 857 - 867

31
[ 61278-21-5 ]
[ 19694-02-1 ]
C₂₀H₁₇NO₃ [ No CAS ]

Reference： [1]Chirality,2018,vol. 30,p. 602 - 608

32
[ 19694-02-1 ]
[ 76587-61-6 ]
C₄₃H₃₇NO₃S [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 8421 - 8424
Angew. Chem.,2018,vol. 130,p. 8557 - 8560,4

33
[ 19694-02-1 ]
2,2'-(((((perfluoropropane-2,2-diyl)bis(4,1-phenylene))bis(oxy))bis(4,1-phenylene))bis(azanediyl))bis(2-oxoethan-1-aminium) [ No CAS ]
N,N'-((((((perfluoropropane-2,2-diyl)bis(4,1-phenylene))bis(oxy))bis(4,1-phenylene))bis(azanediyl))bis(2-oxoethane-2,1-diyl))bis(pyrene-1-carboxamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%		General procedure: A mixture of (tert-butoxycarbonyl)glycine (351mg, 2mmol), hydroxybenzotriazole (HOBt, 405mg, 3mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 575mg, 3mmol) was dissolved in dichloromethane-dimethylformamide (CH2Cl2: DMF (1:1), 20ml) and stirred vigorously at 0C for 20min under an argon atmosphere. Then, 4,4'-(Hexafluoroisopropylene)bis ( p-penyleneoxy) dianiline (HFIBPA) (519mg, 1mmol) and diisopropylethylamine (DIPEA) (388mg, 3mmol) were added to the reaction mixture and stirred at room temperature for another 3h. After completion of the reaction (detected by TLC analysis), the solvent of the reaction mixture was reduced under vacuum. The crude solid was dissolved in H2O and extracted with CH2Cl2, and the organic layer was washed with H2O (2×50mL) and a 5% aqueous NaCl solution (100mL). The collected organic layer was then dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure, and the residue was purified by column chromatography using CH2Cl2 as the eluent to afford compound 7 as a white solid (750mg, 90% yield).

Reference： [1]Dyes and Pigments,2018,vol. 156,p. 307 - 317

34
[ 19694-02-1 ]
3,3'-(((((perfluoropropane-2,2-diyl)bis(4,1-phenylene))bis(oxy))bis(4,1-phenylene))bis(azanediyl))bis(3-oxopropan-1-aminium) [ No CAS ]
N,N'-((((((perfluoropropane-2,2-diyl)bis(4,1-phenylene))bis(oxy))bis(4,1-phenylene))bis(azanediyl))bis(3-oxopropane-3,1-diyl))bis(pyrene-1-carboxamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%		General procedure: A mixture of (tert-butoxycarbonyl)glycine (351mg, 2mmol), hydroxybenzotriazole (HOBt, 405mg, 3mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 575mg, 3mmol) was dissolved in dichloromethane-dimethylformamide (CH2Cl2: DMF (1:1), 20ml) and stirred vigorously at 0C for 20min under an argon atmosphere. Then, 4,4'-(Hexafluoroisopropylene)bis ( p-penyleneoxy) dianiline (HFIBPA) (519mg, 1mmol) and diisopropylethylamine (DIPEA) (388mg, 3mmol) were added to the reaction mixture and stirred at room temperature for another 3h. After completion of the reaction (detected by TLC analysis), the solvent of the reaction mixture was reduced under vacuum. The crude solid was dissolved in H2O and extracted with CH2Cl2, and the organic layer was washed with H2O (2×50mL) and a 5% aqueous NaCl solution (100mL). The collected organic layer was then dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure, and the residue was purified by column chromatography using CH2Cl2 as the eluent to afford compound 7 as a white solid (750mg, 90% yield).

Reference： [1]Dyes and Pigments,2018,vol. 156,p. 307 - 317

35
[ 19694-02-1 ]
[ 180683-64-1 ]
C₂₈H₃₀N₂O₃ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 2115 - 2128

36
[ 19694-02-1 ]
[ 2050-16-0 ]
C₂₉H₁₈N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 72h; Inert atmosphere;

Reference： [1]Yamauchi, Mitsuaki; Yokoyama, Kosuke; Aratani, Naoki; Yamada, Hiroko; Masuo, Sadahiro [Angewandte Chemie - International Edition, 2019, vol. 58, # 40, p. 14173 - 14178][Angew. Chem., 2019, vol. 131, # 40, p. 14311 - 14316,6]

37
[ 110-82-7 ]
[ 19694-02-1 ]
cyclohex-2-en-1-yl 1-pyrenecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With tert.-butylhydroperoxide; (6,8,15,17-tetramethyldibenzo[b,i][1,4,8,11]tetraazacyclotetradecinato)copper(II); In neat (no solvent); at 80℃; for 24h;Schlenk technique; Inert atmosphere;	General procedure: Under an argon atmosphere, [Cu(MeTAA)] (2.0 mg, 0.005 mmol)and benzoic acid (61 mg, 0.5 mmol) were added in an oven-dried Schlenk tube containing a magnetic stir bar. The Schlenk tube wasevacuated and back filled with argon (3 cycles). Subsequently1.50 mmol (3.0 equiv) of TBHP and 1.0 mL cyclohexane were injected to the Schlenk tube via a syringe. Then the Schlenk tube was placed intoan oil bath and heated at 80 C for 24 h. Once the reaction was completed,the reaction mixture was concentrated in vacuum and the residuewas dissolved in dichloromethane and purified by column chromatographyusing silica and hexane was used as eluent.

Reference： [1]Inorganica Chimica Acta,2020,vol. 500

38
[ 19694-02-1 ]
[ 4559-70-0 ]
diphenyl(pyren-1-yl)phosphine oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With bis(1,5-cyclooctadiene)nickel (0); N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; 2,2-dimethylpropanoic anhydride; In 1,4-dioxane; at 120℃; for 18h;Schlenk technique; Inert atmosphere; Glovebox;	Weigh 1.2 times equivalent of 1-acetic acid (0.48mmol), take 1.0 times equivalent of diphenylphosphine (HP (O) Ph2) and 10mol% Ni (cod) 2, 10mol% in the glove box dppp, 2.5 times equivalent CyNMe2, 1.5 times equivalent Piv2O were added to the Schlenk reaction tube in sequence,Subsequently, in a nitrogen atmosphere, 3 ml of dioxane solvent was added.The reaction was continued at 120 C for 18h.After the reaction, it was cooled to room temperature and separated by column chromatography.The target product is obtained: 1-fluorenylphenyl phosphorus oxide,The yield was 78%.

Reference： [1]Patent: CN110540552,2019,A .Location in patent: Paragraph 0038- 0040
[2]European Journal of Organic Chemistry,2020,vol. 2020,p. 1148 - 1153

39
[ 19694-02-1 ]
[ 501-65-5 ]
[ 2482501-48-2 ]
[ 2482501-54-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 72% 2: 36%	With bis[dichlorido(η⁵-1,2,3,4,5-pentamethyl-cyclopentadienyl)rhodium (III)]; Cu(OAc)₂*H₂O In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere;	4.3. General procedures for the oxidative coupling of carboxylic acids with internal alkynes. Conditions B and C General procedure: Under argon to a mixture of arylcarboxylic acid (0.5 mmol), alkyne(0.5 mmol or 1.0 mmol), catalyst ([Cp*RhCl2]2 or [CpRhI2]n; 0.005 mmol, 1 mol% Rh), oxidizing agent (1 mmol of Cu(OAc)2•H2O in the case of conditions B or 0.7 mmol of Ag2CO3 in the case of conditions C), 3 ml of DMF was added. The resulting mixture was refluxed with vigorous stirring in an oil bath at 120 C for 8 h. After cooling, CH2Cl2 was added to the reaction mixture. The precipitate of copper salts was centrifuged off. The reaction mixture was washed several times with saturated NaCl(aq) solution using a separating funnel to remove DMF. The organic layer was dried over anhydrous Na2SO4. The solvent was removed in vacuo and the residue was chromatographed on a silica column (~15 cm). Hexane was used as the first eluent to remove excess of unreacted alkyne, then the desired products were eluted with mixtures of hexane with dichloromethane, or diethyl ether, or ethyl acetate (see below for specific ratios for each compound). Removal of the solvent in vacuo gives the corresponding isocoumarin or naphthalene derivatives. To obtain analytical pure compounds, recrystallization should be carried out from methanol or by slow interdiffusion of a two-phase system containing hexane and a solution of the compound in dichlorometane.
1: 29% 2: 36%	With bis[dichlorido(η⁵-1,2,3,4,5-pentamethyl-cyclopentadienyl)rhodium (III)]; copper(II) acetate dihydrate In 1,2-dimethylbenzene at 150℃; for 6h; Inert atmosphere;
1: 29% 2: 36%	With bis[dichlorido(η⁵-1,2,3,4,5-pentamethyl-cyclopentadienyl)rhodium (III)] In 1,2-dimethylbenzene at 150℃; for 6h; Inert atmosphere;	4.3. General procedures for the oxidative coupling of carboxylic acids with internal alkynes. Conditions B and C General procedure: Under argon to a mixture of arylcarboxylic acid (0.5 mmol), alkyne(0.5 mmol or 1.0 mmol), catalyst ([Cp*RhCl2]2 or [CpRhI2]n; 0.005 mmol, 1 mol% Rh), oxidizing agent (1 mmol of Cu(OAc)2•H2O in the case of conditions B or 0.7 mmol of Ag2CO3 in the case of conditions C), 3 ml of DMF was added. The resulting mixture was refluxed with vigorous stirring in an oil bath at 120 C for 8 h. After cooling, CH2Cl2 was added to the reaction mixture. The precipitate of copper salts was centrifuged off. The reaction mixture was washed several times with saturated NaCl(aq) solution using a separating funnel to remove DMF. The organic layer was dried over anhydrous Na2SO4. The solvent was removed in vacuo and the residue was chromatographed on a silica column (~15 cm). Hexane was used as the first eluent to remove excess of unreacted alkyne, then the desired products were eluted with mixtures of hexane with dichloromethane, or diethyl ether, or ethyl acetate (see below for specific ratios for each compound). Removal of the solvent in vacuo gives the corresponding isocoumarin or naphthalene derivatives. To obtain analytical pure compounds, recrystallization should be carried out from methanol or by slow interdiffusion of a two-phase system containing hexane and a solution of the compound in dichlorometane.

Reference： [1]Arsenov, Mikhail A.; Fedorov, Yury V.; Muratov, Dmitry V.; Nelyubina, Yulia V.; Loginov, Dmitry A. [Dyes and Pigments, 2022, vol. 206]
[2]Molotkov, Alexander P.; Arsenov, Mikhail A.; Kapustin, Daniil A.; Muratov, Dmitry V.; Shepel', Nikolay E.; Fedorov, Yury V.; Smol'yakov, Alexander F.; Knyazeva, Elena I.; Lypenko, Dmitry A.; Dmitriev, Artem V.; Aleksandrov, Alexey E.; Maltsev, Eugeny I.; Loginov, Dmitry A. [ChemPlusChem, 2020, vol. 85, # 2, p. 334 - 345]
[3]Arsenov, Mikhail A.; Fedorov, Yury V.; Muratov, Dmitry V.; Nelyubina, Yulia V.; Loginov, Dmitry A. [Dyes and Pigments, 2022, vol. 206]

40
[ 19694-02-1 ]
[ 501-65-5 ]
[ 2482501-54-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With Cu(OAc)₂*H₂O; [CpRhI₂]_n In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere;	4.3. General procedures for the oxidative coupling of carboxylic acids with internal alkynes. Conditions B and C General procedure: Under argon to a mixture of arylcarboxylic acid (0.5 mmol), alkyne(0.5 mmol or 1.0 mmol), catalyst ([Cp*RhCl2]2 or [CpRhI2]n; 0.005 mmol, 1 mol% Rh), oxidizing agent (1 mmol of Cu(OAc)2•H2O in the case of conditions B or 0.7 mmol of Ag2CO3 in the case of conditions C), 3 ml of DMF was added. The resulting mixture was refluxed with vigorous stirring in an oil bath at 120 C for 8 h. After cooling, CH2Cl2 was added to the reaction mixture. The precipitate of copper salts was centrifuged off. The reaction mixture was washed several times with saturated NaCl(aq) solution using a separating funnel to remove DMF. The organic layer was dried over anhydrous Na2SO4. The solvent was removed in vacuo and the residue was chromatographed on a silica column (~15 cm). Hexane was used as the first eluent to remove excess of unreacted alkyne, then the desired products were eluted with mixtures of hexane with dichloromethane, or diethyl ether, or ethyl acetate (see below for specific ratios for each compound). Removal of the solvent in vacuo gives the corresponding isocoumarin or naphthalene derivatives. To obtain analytical pure compounds, recrystallization should be carried out from methanol or by slow interdiffusion of a two-phase system containing hexane and a solution of the compound in dichlorometane.
52%	With copper(II) acetate dihydrate; [CpRhI₂]_n In 1,2-dimethylbenzene at 150℃; for 6h; Inert atmosphere;

Reference： [1]Arsenov, Mikhail A.; Fedorov, Yury V.; Muratov, Dmitry V.; Nelyubina, Yulia V.; Loginov, Dmitry A. [Dyes and Pigments, 2022, vol. 206]
[2]Molotkov, Alexander P.; Arsenov, Mikhail A.; Kapustin, Daniil A.; Muratov, Dmitry V.; Shepel', Nikolay E.; Fedorov, Yury V.; Smol'yakov, Alexander F.; Knyazeva, Elena I.; Lypenko, Dmitry A.; Dmitriev, Artem V.; Aleksandrov, Alexey E.; Maltsev, Eugeny I.; Loginov, Dmitry A. [ChemPlusChem, 2020, vol. 85, # 2, p. 334 - 345]

41
[ 16494-36-3 ]
[ 19694-02-1 ]
C₂₂H₁₄O₂S [ No CAS ]

Reference： [1],2020,vol. 11,p. 2472 - 2478

42
[ 98027-84-0 ]
[ 19694-02-1 ]
C₂₂H₁₁Cl₂NO₂ [ No CAS ]

Reference： [1]Chemical Science,2020,vol. 11,p. 2472 - 2478

43
[ 19694-02-1 ]
C₇H₁₄N₄O₂*ClH [ No CAS ]
C₂₄H₂₂N₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With 2-(6-chloro-1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate; benzotriazol-1-ol; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 24h;Inert atmosphere;	Azide 6 (55 mg, 0.25 mmol) and <strong>[19694-02-1]1-pyrenecarboxylic acid</strong> (61 mg, 0.25mmol) were dissolved in dry DMF (2.5 mL) under argon and HOBt (33.5 mg, 0.25 mmol), HCTU(102.5 mg, 0.25 mmol) and dry Et3N (138 muL, 1.0 mmol) were added. The reaction was stirred at room temperature overnight. Product 7 (91 mg, 87%) was isolated by preparative chromatography(CH2Cl2/CH3OH 20:1) as a light yellow oil. Rf = 0.85 (CH2Cl2/CH3OH 20:1); 1H NMR (600 MHz, DMSOd6)delta/ppm: 8.70 (t, J = 5.3 Hz, 1H), 8.48 (d, J = 9.2 Hz, 1H), 8.36-8.32 (m, 3H, Py), 8.26-8.22 (m, 3H, Py),8.13 - 8.10 (m, 2H, Py), 4.34 (dd, J = 8.2, 5.0 Hz, 1H, CH), 3.74 (s, 3H, OCH3), 3.42 (dd, J = 12.7, 6.7 Hz,2H, CH2), 1.90-1.73 (m, 2H, CH2), 1.70-1.63 (m, 2H, CH2), 1.53-1.48 (m, 2H, CH2); 13C NMR (75 MHz,DMSO-d6): 170.8, 168.8, 132.3, 131.5, 130.7, 130.2, 128.2, 128.0, 127.7, 127.2, 126.6, 125.8, 125.6, 125.1,124.7, 124.4, 123.8, 123.7, 61.2, 52.5, 38.9, 30.5, 28.6, 22.7. ESI-MS: m/z calcd. for C24H23N4O3 [M+H]+415.46, found 415.2.

Reference： [1]Molecules,2020,vol. 25

44
[ 19694-02-1 ]
[ 76115-06-5 ]
[ 2522584-73-0 ]

Yield	Reaction Conditions	Operation in experiment
78.7%	Stage #1: Pyrene-1-carboxylic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Stage #2: 1-(4'-hydroxyphenyl)-1,2,2-triphenylethylene In N,N-dimethyl-formamide at 85℃; for 18h; Inert atmosphere;	2.3.1 4-(1,2,2-triphenylvinyl)phenyl pyrene-1-carboxylate (1) 1-Pyrenecarboxylic acid (369mg, 1.5mmol), EDC·HCl (574mg, 3mmol), and dimethylaminopyridine (110mg, 0.9mmol) were dissolved in dry DMF (20mL). After stirring for 30min, 4-(1,2,2-triphenylvinyl)phenol (522mg, 1.5mmol) were added and the resulting mixture was stirred and heated at 85°C for 18h. After cooling, the mixture was diluted with EtOAc, washed with water and brine, dried over Na2SO4. The solvents were removed under reduced pressure. The residue was purified by chromatography on a silica gel column (petroleum ether/dichloromethane=10/1) to yield the compound 1 (0.68g, 78.7%) as a pale yellow powder. 1H NMR (500MHz, CDCl3): δ (ppm)=9.36 (d, J=9.5Hz, 1H), 8.86 (d, J=8.5Hz, 1H), 8.20 (dd, J=14.0, 6.5Hz, 3H), 8.14 (d, J=8.5Hz, 2H), 8.04 (d, J=9.0Hz, 1H), 8.00 (t, J=7.5Hz, 1H), 7.12-7.05 (m, 9H), 7.05-7.00 (m, 8H), 6.98-6.96 (m, 2H) (Fig. S7); 13C NMR (126MHz, CDCl3): δ (ppm)=166.3, 149.7, 143.8, 143.8, 143.7, 141.5, 140.2, 135.1, 132.6, 132.0, 131.6, 131.5, 131.5, 131.1, 130.5, 130.2, 130.0, 129.1, 128.0, 127.9, 127.8, 127.3, 126.8, 126.7, 126.6, 126.6, 125.1, 124.9, 124.3, 124.3, 122.3, 121.3 (Fig. S8); HRMS (ESI): m/z calcd. for C43H28KO2: 615.1726 [M+K]+, found: 615.1724 (Fig. S9); element analysis calcd. (%) for C43H28O2: C, 89.56; H, 4.89; found: C, 89.14; H, 4.98.

Reference： [1]Zhang, Hongyan; Zhang, Han; Huang, Guangxi; Li, Bing Shi [Dyes and Pigments, 2021, vol. 185]

45
[ 2038-03-1 ]
[ 19694-02-1 ]
[ 2622330-78-1 ]

Yield	Reaction Conditions	Operation in experiment
39%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	1-Pyrenecarboxylic acid (0.616 g, 0.25 mmol) and N-(2-aminoethyl)morpholine (0.1295 g, 0.995 mmol) were dissolved in 15.0 mldichloromethane. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride(EDC.HCl) (0.2460 g, 1.28 mmol) was then added, and themixture was stirred at room temperature for 24 h; thin-layer chromatography(TLC) was used to monitor the reaction. After the reaction wascompleted, the organic solvent was removed with the assistance of rotaryevaporator. The crude product was further purified through columnchromatography (dichloromethane/methanol, 5:1) to obtain a lightyellow solid MPCA (0.0901 g) with a 39% yield. 1H NMR (600 MHz,DMSO-d6, /ppm,) 8.63 - 8.59 (m, 2H), 8.36 (d, J = 7.9, 2H), 8.34 (d, J= 7.8 Hz, 1H), 8.29 - 8.25 (m, 2H), 8.25 - 8.21 (m, 1H), 8.12 (dd, J =15.4, 7.7 Hz, 2H), 3.67 (t, J = 4.5 Hz, 4H), 3.56 (q, J = 6.4 Hz, 2H), 2.61(t, J = 6.6 Hz, 2H), 2.57 - 2.48 (m, 4H). 13C NMR (151 MHz, DMSO-d6,/ppm): 169.29, 131.92, 131.20, 130.72, 128.67, 128.45, 128.13,127.70, 127.07, 127.05, 126.22, 126.03, 126.00, 125.55, 125.38,124.94, 124.23, 124.14, 66.83, 57.81, 57.78, 53.81, 36.92. HRMS:359.17878; calcd for [MPCA + H]+ (C23H23O2N2), 359.17595 (seeFigs. S3-S5 in Supporting Information).

Reference： [1]Huang, Zijie; Lei, Xiaolan; Li, Ligui; Liu, Hong; Ma, Li-Jun; Sun, Fengqiang; Wang, Sha; Wang, Yan; Yang, Liting; Zhang, Zhongyan [Journal of Photochemistry and Photobiology A: Chemistry, 2021, vol. 418]

46
[ 19694-02-1 ]
[ 20439-47-8 ]
[ 256474-19-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 120h;
89 %	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;

Reference： [1]Hu, Liangyu; Hu, Song; Liu, Minghua; Wang, Yuan; Zhu, Xuefeng [Angewandte Chemie - International Edition, 2021, vol. 60, # 35, p. 19451 - 19457][Angew. Chem., 2021, vol. 133, # 35, p. 19600 - 19606]
[2]Álvaro-Martins, Maria João; Billiaux, Chloé; Godard, Pascale; Oda, Reiko; Raffy, Guillaume; Bassani, Dario M. [Chemical Communications, 2023, vol. 59, # 51, p. 7963 - 7966]

47
[ 19694-02-1 ]
[ 21436-03-3 ]
[ 256474-21-2 ]

Yield	Reaction Conditions	Operation in experiment
94.7%	With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 120h;
86 %	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;

Reference： [1]Hu, Liangyu; Hu, Song; Liu, Minghua; Wang, Yuan; Zhu, Xuefeng [Angewandte Chemie - International Edition, 2021, vol. 60, # 35, p. 19451 - 19457][Angew. Chem., 2021, vol. 133, # 35, p. 19600 - 19606]
[2]Álvaro-Martins, Maria João; Billiaux, Chloé; Godard, Pascale; Oda, Reiko; Raffy, Guillaume; Bassani, Dario M. [Chemical Communications, 2023, vol. 59, # 51, p. 7963 - 7966]

48
[ 19694-02-1 ]
[ 146504-07-6 ]
[ 2691796-98-0 ]

Yield	Reaction Conditions	Operation in experiment
91.2%	With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 72h;
71 %	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;

Reference： [1]Hu, Liangyu; Hu, Song; Liu, Minghua; Wang, Yuan; Zhu, Xuefeng [Angewandte Chemie - International Edition, 2021, vol. 60, # 35, p. 19451 - 19457][Angew. Chem., 2021, vol. 133, # 35, p. 19600 - 19606]
[2]Álvaro-Martins, Maria João; Billiaux, Chloé; Godard, Pascale; Oda, Reiko; Raffy, Guillaume; Bassani, Dario M. [Chemical Communications, 2023, vol. 59, # 51, p. 7963 - 7966]

49
[ 19694-02-1 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
81%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃;	1.3 General procedure: In the second step, the deprotected monomer M0 (2-(1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H- 4,7-epoxyisoindol-2-yl)-3-(2-formyl-3-methylphenoxy)propan-1-aminium 2,2,2-trifluoro- acetate, 117.60 mg, 0.478 mmol, 1.09 eq.), the fluorophore-linker carboxylic acid (F1-3-L- COOH, 1.25 eq.) and HOBt (65.12 mg, 0.482 mmol, 1.10 eq.) were dissolved in N,N- dimethylformamide (13 mL) and the mixture placed on an ice bath. 1-ethyl-3-(3- dimethylaminopropyl)carbodiimide (96.58 mg, 0.504 mmol, 1.15 eq.) and afterwards N,N- diisopropylethylamine (228.6 μL, 169.9 mg, 1.314 mmol, 3.0 eq., dissolved in 5 mL dry DMF) were added via a syringe during 20 min. The reaction mixture is stirred at 0 °C for 2 h and subsequently over night at ambient temperature. The reaction mixture is diluted in 100 ml ethyl acetate, washed with twice with 25 ml 1N HCl, twice with 25 ml saturated NaHCO3- solution and finally with 40 ml brine. The organic layer is dried over Na2SO4 and the solvent is removed in vacuo. The crude product is purified via flash chromatography (gradient CH:EE 30:70-90:10 v/v).

Reference： [1]Current Patent Assignee: QUEENSLAND UNIVERSITY OF TECHNOLOGY - WO2021/207793, 2021, A1 Location in patent: Page/Page column 52; 54-55

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CAS No. :	19694-02-1	MDL No. :	MFCD00192424
Formula :	C₁₇H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HYISVWRHTUCNCS-UHFFFAOYSA-N
M.W :	246.26	Pubchem ID :	125395
Synonyms :

Num. heavy atoms :	19
Num. arom. heavy atoms :	16
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	77.11
TPSA :	37.3 Å²

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) :	-4.28 cm/s

Log Po/w (iLOGP) :	1.97
Log Po/w (XLOGP3) :	4.96
Log Po/w (WLOGP) :	4.28
Log Po/w (MLOGP) :	3.9
Log Po/w (SILICOS-IT) :	4.14
Consensus Log Po/w :	3.85

[ CAS No. 19694-02-1 ] {[proInfo.proName]}

Quality Control of [ 19694-02-1 ]

Related Doc. of [ 19694-02-1 ]

Product Details of [ 19694-02-1 ]

Calculated chemistry of [ 19694-02-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 19694-02-1 ]

[ 19694-02-1 ] Synthesis Path-Upstream 1~3

[ 19694-02-1 ] Synthesis Path-Downstream 1~49

Related Functional Groups of
[ 19694-02-1 ]

Aryls

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

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Inquiry

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

Log S (ESOL) :	-5.05
Solubility :	0.0022 mg/ml ; 0.00000894 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.48
Solubility :	0.000813 mg/ml ; 0.0000033 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.96
Solubility :	0.000269 mg/ml ; 0.00000109 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.0

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:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 19694-02-1 ] {[proInfo.proName]}

Quality Control of [ 19694-02-1 ]

Related Doc. of [ 19694-02-1 ]

Product Details of [ 19694-02-1 ]

Calculated chemistry of [ 19694-02-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 19694-02-1 ]

Application In Synthesis of [ 19694-02-1 ]

[ 19694-02-1 ] Synthesis Path-Upstream 1~3

[ 19694-02-1 ] Synthesis Path-Downstream 1~49

Related Functional Groups of [ 19694-02-1 ]

Aryls

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 19694-02-1 ]