[ CAS No. 2595-90-6 ] {[proInfo.proName]}

Name: 2595-90-6|1-(Bromomethyl)pyrene|90%
Brand: Ambeed
SKU: A734717
Rating: 90 (27 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 2595-90-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 2595-90-6 ]

Product Details of [ 2595-90-6 ]

CAS No. :	2595-90-6	MDL No. :	MFCD00269937
Formula :	C₁₇H₁₁Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UGMXRPVWWWDPFC-UHFFFAOYSA-N
M.W :	295.17	Pubchem ID :	1274043
Synonyms :

Calculated chemistry of [ 2595-90-6 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	16
Fraction Csp3 :	0.06
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	82.98
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.9
Log Po/w (XLOGP3) :	5.59
Log Po/w (WLOGP) :	5.33
Log Po/w (MLOGP) :	5.24
Log Po/w (SILICOS-IT) :	5.79
Consensus Log Po/w :	4.97

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-5.78
Solubility :	0.000486 mg/ml ; 0.00000165 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.35
Solubility :	0.00131 mg/ml ; 0.00000445 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-7.83
Solubility :	0.00000436 mg/ml ; 0.0000000148 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.78

Safety of [ 2595-90-6 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P261-P264-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P310-P321-P332+P313-P362-P403+P233-P405-P501	UN#:	3261
Hazard Statements:	H315-H318-H335-H413	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 2595-90-6 ]

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

Upstream synthesis route of [ 2595-90-6 ]
Downstream synthetic route of [ 2595-90-6 ]

[ 2595-90-6 ] Synthesis Path-Upstream 1~4

1
[ 2595-90-6 ]
[ 3029-19-4 ]

Reference： [1] Chemistry Letters, 2005, vol. 34, # 2, p. 194 - 195

2
[ 51694-22-5 ]
[ 2595-90-6 ]
[ 56790-59-1 ]
[ 3029-19-4 ]

Reference： [1] Tetrahedron Letters, 2012, vol. 53, # 30, p. 3843 - 3846

3
[ 2595-90-6 ]
[ 24463-15-8 ]

Reference： [1] Tetrahedron Letters, 2012, vol. 53, # 30, p. 3843 - 3846

4
[ 2595-90-6 ]
[ 24463-15-8 ]
[ 1086-00-6 ]

Reference： [1] Tetrahedron Letters, 2012, vol. 53, # 30, p. 3843 - 3846

[ 2595-90-6 ] Synthesis Path-Downstream 1~88

1
[ 2381-21-7 ]
[ 2595-90-6 ]

Reference： [1]Journal of the Chemical Society,1965,vol. 65,p. 1829 - 1843

2
[ 3029-19-4 ]
[ 2595-90-6 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1960,vol. 69,p. 563 - 569
[2]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 2881 - 2890
[3]Chemical Communications,2013,vol. 49,p. 478 - 480
[4]Supramolecular Chemistry,2013,vol. 25,p. 69 - 78
[5]Inorganic Chemistry,2017,vol. 56,p. 13715 - 13731
[6]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2018,vol. 204,p. 425 - 431
[7]ChemPlusChem,2019,vol. 84,p. 130 - 135
[8]Journal of Inorganic Biochemistry,2020,vol. 202

3
[ 24463-15-8 ]
[ 2595-90-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With phosphorus tribromide; In tetrahydrofuran; at 20℃; for 0.5h;	Phosphorus tribromide (1.75 g) was dissolved in tetrahydrofuran (5 mL).Pyrenebenzyl alcohol (1.00 g) was added to the above solution in portions and the reaction was continued after the reaction was continued at room temperature for 30 minutes.The reaction mixture was suction filtered and washed with diethyl ether to give the target pyrene benzyl bromide (1.22 g, 96%).
	With phosphorus tribromide; In tetrahydrofuran; at 20℃; for 1h;	1-Pyrenecarboxaldehyde (1e) was purchased from Sigma-Aldrichand used as received. 1d (pyren-1-ylmethanol), 1c (1-(bromomethyl)pyrene) and 1b (diethyl (pyren-1-ylmethyl)phosphonate) were synthesizedfollowing previous reports with some modifications [14,16-22]. Briefly, the procedure to synthesize 1b is as follows: 1e (230 mg, 1.0 mmol) was poured into anhydrous methanol (40 ml)resulting into a suspension and to this excess of NaBH4 (380 mg,10.0 mmol) was added in portions at 0 C. The mixture was stirred for1 h at room temperature and then refluxed for 4 h. The mixture wascooled and saturated aq. NH4Cl was added to get a white precipitate. Itwas extracted with dichloromethane (5 × 10 ml) and dried with anhydrousNa2SO4. The solvent was evaporated to obtain a pale yellowcoloured solid 1d. Thus obtained 1d (186 mg, 0.8 mmol) was takeninto dry THF (4 ml) forming a suspension and PBr3 (0.114 ml,1.2 mmol) and was added to the mixture. The mixture was stirred for1 h at room temperature. The residue was filtered and washed withEt2O to give the desired product 1c. The mixture of 1c (147 mg,0.5 mmol) and an excess amount of triethyl phosphite (2 ml) wastaken in CHCl3 (10 ml) and refluxed overnight in inert atmosphere.The mixture was settled down to room temperature and the excesstriethyl phosphite was evaporated under reduced pressure. The crudeproduct was purified by column chromatography using 1-10% methanol/dichloromethane to give white coloured 1b. An excess amount ofNaH (43 mg, 1.8 mmol, 6 equiv.) was added gradually to a solution ofphosphonate derivative 1b (106 mg, 0.3 mmol) in dry THF (30 ml)and the mixture was stirred for 1 h at room temperature. To this,terephthalaldehyde (41mg, 0.3mmol)was added at once. Themixturewas stirred overnight in dark at room temperature. 10 ml of distilledwater was added upon completion of the reaction to destroy excessNaH present in the solution. The solvents were evaporated using a rotaryevaporator (procured fromCitizen) and the crude product was purifiedby column chromatography using 10-60% of hexane/dichloromethane mixture as eluent. The solvents were evaporated toobtain the orange-yellow coloured 1a ((E)-4-(2-(pyren-1-yl)vinyl)benzaldehyde). The mixture of 1a (33.2 mg, 0.1 mmol) and 3-ethyl-2-methylbenzothiazolium iodide (43 mg, 0.14 mmol) was dissolved inmethanol (20 ml). An excess amount of NaOMe (~10 equiv.) wasadded to the mixture and refluxed overnight. The initial yellowsolutionturned intowine-red coloured solution at the end of reflux. Themixturewas cooled to room temperature and methanol was evaporated. Thewhole process has been represented by Scheme 2. The crude productwaswashedwith distilledwater, dried and purified by column chromatographyusing 1-10% methanol/dichloromethane mixture as eluent toobtain the red-brown coloured 1 (3-ethyl-2-((Z)-4-((E)-2-(pyren-1-yl)vinyl)styryl)benzo[d]thiazol-3-ium) (Scheme 1). 1H NMR (400 MHz,DMSO d6): delta (ppm) 8.857 (d, 1H, J = 9.92 Hz), 8.655 (d, 1H, J =16.04 Hz), 8.592 (d, 1H, J = 8.40 Hz), 8.460 (d, 1H, J = 8.4 Hz),8.368-8.286 (m, 6H), 8.221 (s, 2H), 8.183 (d, 2H, J = 8.4Hz),8.123-8.089 (m, 4 H), 7.900 (t, 1H, J = 7.26 Hz), 7.814 (t, 1H, J =8.02 Hz), 7.704 (d, 1H, J = 16.04 Hz), 5.013 (q, 2H, J=7.12 Hz), 1.514(t, 3H, J = 7.26 Hz), ESI-MS (m/z): calculated - 492.18, found - 493.19[M + H]+.
0.8 g	With phosphorus tribromide; In toluene; at 0℃; for 0.5h;Inert atmosphere;	Under the protection of Ar gas, put 1.0 g of pyrene methanol in a three-necked flask, and add 50 mL of freshly distilled toluene to the three-necked flask.The three-necked flask was cooled to 0 C, and then 0.5 mL of phosphorus tribromide was added dropwise to the system.After the addition was complete, stirring was continued at this temperature for 30 min.Then stirred at room temperature until the solution was clear.After the reaction was completed, 26 mL of a saturated sodium carbonate solution was added, and the layers separated, and the organic phase was washed twice with 26 mL of water and saturated brine, respectively. Followed by anhydrous magnesium sulfate, filtered, and then distilled off on a rotary evaporator most of the toluene, crystallization was cooled to give crystals after bromomethyl pyrene, filtered, and dried in vacuo to give bromomethyl pyrene 0.8g.The 0.8g bromomethyl pyrene was dissolved in 16mL of toluene,Add an equimolar amount of cetyl tertiary amine to the system,Stir at 50 C for 48 hours, during which a white precipitate appears.After the reaction was completed, the solid was filtered and the solid was washed with a small amount of toluene.Compound A was obtained by vacuum drying.Its structural formula is as follows

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 9633 - 9637,5
Angewandte Chemie,2012,vol. 124,p. 9771 - 9775,5
[2]Journal of the American Chemical Society,2003,vol. 125,p. 2838 - 2839
[3]Patent: CN106349287,2017,A .Location in patent: Paragraph 0022
[4]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 3158 - 3162
[5]Inorganic Chemistry,2017,vol. 56,p. 13715 - 13731
[6]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2010,vol. 67,p. 19 - 27
[7]Chemical Communications,2013,vol. 49,p. 11698 - 11700
[8]Journal of the American Chemical Society,2008,vol. 130,p. 12846 - 12847
[9]Chemical Communications,2009,p. 5573 - 5575
[10]Organic Letters,2007,vol. 9,p. 417 - 420
[11]Journal of Organic Chemistry,2008,vol. 73,p. 8212 - 8218
[12]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 2881 - 2890
[13]Journal of Polymer Science, Part A: Polymer Chemistry,2014,vol. 52,p. 321 - 329
[14]Chemical Communications,2013,vol. 49,p. 478 - 480
[15]Supramolecular Chemistry,2013,vol. 25,p. 69 - 78
[16]Journal of medicinal chemistry,1972,vol. 15,p. 68 - 70
[17]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 2231 - 2236
[18]Photochemistry and Photobiology,1999,vol. 69,p. 513 - 516
[19]Journal of Physical Chemistry B,2004,vol. 108,p. 13265 - 13272
[20]Journal of the American Chemical Society,2009,vol. 131,p. 15528 - 15533
[21]Organic Letters,2009,vol. 11,p. 4294 - 4297
[22]Chemical Communications,2012,vol. 48,p. 6007 - 6009
[23]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 635 - 637
[24]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2018,vol. 204,p. 425 - 431
[25]ChemPlusChem,2019,vol. 84,p. 130 - 135
[26]Journal of Inorganic Biochemistry,2020,vol. 202
[27]Patent: CN110590617,2019,A .Location in patent: Paragraph 0022-0024

4
[ 2595-90-6 ]
[ 603-35-0 ]
[ 33895-37-3 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; for 24h;Reflux; Inert atmosphere;	To a solution 0.295 g (1.0 mmol) of 1-bromomethyl pyrene 2 in 30 mL of CH3CN was added 0.524g (0.5 mmol) of triphenylphosphine and the reaction mixture was refluxed for 1 days under the nitrogen atmosphere. After cooling down to room temperature, the pale yellow solid was obtained by filtration. The filtered solid was added in 20mL MeOH with NaPF6. The yellow solid was obtained by filtration to yield 0.5 g (95%) of 1.

Reference： [1]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 2881 - 2890
[2]Bulletin des Societes Chimiques Belges,1960,vol. 69,p. 563 - 569
[3]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 2231 - 2236
[4]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 635 - 637

5
[ 2595-90-6 ]
[ 121-69-7 ]
[ 38801-65-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1981,vol. 54,p. 3304 - 3311

6
[ 2595-90-6 ]
[ 100-10-7 ]
[ 80525-75-3 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1981,vol. 54,p. 3304 - 3311

7
[ 2595-90-6 ]
[ 485-71-2 ]
N-[(1-pyrenyl)methyl]cinchonidinium bromide [ No CAS ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 1443 - 1447

8
(1α,4α,4aβ,5β,7β,7aβ,8α,11α,11aβ,12β,14β,14aβ)-1,4,4a,5,7,7a,8,11,11a,12,14,14a-dodecahydro-6,13-dimethoxy-5,14:7,12-dietheno-1,4:8,11-di(endo-hydroxymethano)pentacene [ No CAS ]
[ 2595-90-6 ]
(1α,4α,4aβ,5β,7β,7aβ,8α,11α,11aβ,12β,14β,14aβ)-1,4,4a,5,7,7a,8,11,11a,12,14,14a-dodecahydro-6,13-dimethoxy-5,14:7,12-dietheno-1,4:8,11-di(endo-(1-pyrenylmethoxy)methano)pentacene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 9717 - 9726

9
[ 2595-90-6 ]
[ 169331-67-3 ]
6-(1-pyrenylmethyl)-1,11-dimethyl-3,9,12,15,18,20,23-heptaoxa-6-azabicyclo[9.7.6]tetracosane [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 1787 - 1794

10
[ 2595-90-6 ]
[ 66943-05-3 ]
N-(1-pyrenylmethyl)-1,4,7,10-tetraoxa-13-azacyclopentadecane [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 1787 - 1794

11
[ 754-96-1 ]
[ 2595-90-6 ]
[ 904684-53-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2399 - 2407

12
[ 112-47-0 ]
[ 2595-90-6 ]
[ 904684-56-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2399 - 2407

13
[ 2595-90-6 ]
1-(n-butyl)-4,4'-bipyridinium bromide [ No CAS ]
1-[(pyren-1-yl)methyl]-1'-butyl-4,4'-bipyridinium dibromide [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 417 - 420

14
[ 2595-90-6 ]
[ 121-44-8 ]
[(pyren-1-yl)methyl]triethylammonium bromide [ No CAS ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4014 - 4017
[2]Organic Letters,2007,vol. 9,p. 417 - 420

15
[ 2595-90-6 ]
2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-10-(pyren-1-ylmethoxy)decyl-N-methylisonicotinium iodide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2399 - 2407

16
[ 2595-90-6 ]
10-(pyren-1-ylmethoxy)decyl-N-methylisonicotinium iodide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2399 - 2407

17
[ 2595-90-6 ]
[ 904684-54-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2399 - 2407

18
[ 2595-90-6 ]
[ 904684-57-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2399 - 2407

19
[ 2595-90-6 ]
[ 691398-11-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 3548 - 3556
[2]Organic Letters,2004,vol. 6,p. 1489 - 1492

20
[ 2595-90-6 ]
N-[(1-pyrenyl)methyl]-O⁽⁹⁾-allylhydrocinchonidinium bromide [ No CAS ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 1443 - 1447

21
[ 2595-90-6 ]
N-[(1-pyrenyl)methyl]-O⁽⁹⁾-allylcinchonidinium bromide [ No CAS ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 1443 - 1447

22
[ 2595-90-6 ]
(1S,2S,4S,5R)-2-[(R)-(Anthracen-9-ylmethoxy)-quinolin-4-yl-methyl]-5-ethyl-1-pyren-1-ylmethyl-1-azonia-bicyclo[2.2.2]octane; bromide [ No CAS ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 1443 - 1447

23
[ 2595-90-6 ]
[ 100442-89-5 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 2838 - 2839

24
[ 2595-90-6 ]
[ 87147-90-8 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 2838 - 2839

25
[ 2595-90-6 ]
[ 91859-60-8 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 2838 - 2839

26
[ 2595-90-6 ]
[ 176650-99-0 ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 4354 - 4360

27
[ 2595-90-6 ]
[ 176651-01-7 ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 4354 - 4360

28
[ 2595-90-6 ]
[ 176651-00-6 ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 4354 - 4360

29
[ 2595-90-6 ]
(3-{3,5-Bis-[3-(pyren-1-ylmethoxy)-benzyloxy]-benzyloxy}-phenyl)-dimethyl-amine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 4354 - 4360

30
[ 2595-90-6 ]
[ 38764-40-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1981,vol. 54,p. 3304 - 3311

31
[ 2595-90-6 ]
[ 132975-08-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 2881 - 2890

32
[ 2595-90-6 ]
[ 102699-19-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 2881 - 2890

33
[ 2595-90-6 ]
(E)-1,2-di(pyren-1-yl)ethylene [ No CAS ]

Reference： [1]Bulletin des Societes Chimiques Belges,1960,vol. 69,p. 563 - 569

34
[ 2595-90-6 ]
[ 33895-41-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 2231 - 2236

35
[ 2595-90-6 ]
[ 33895-39-5 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 2231 - 2236

36
[ 2595-90-6 ]
[ 568599-06-4 ]
Diethyl-2-(1-pyrenyhnethyl)-2-acetamidomalonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.1%	In tetrahydrofuran; CH2Cl2:H2O; ethanol;	Diethyl-2-(1-pyrenyhnethyl)-2-acetamidomalonate. A 9.78 g (45.04 mmol) sample of diethyl acetamidomalonate, and 1.08 g sodium hydride (45.04 mmol) were suspended in 100 mL of anhydrous THF, under nitrogen, and at 0 C. After stirring for 5 min., 2.5 mL of anhydrous ethanol were added slowly, and the solution returned to r.t. A solution of 1-(bromomethyl)pyrene (12.03 g, 40.9 mmol, dissolved in 100 mL dry THF) was slowly added to the reaction mixture, and the solution brought to reflux for 18 h. The bulk of the THF was removed under reduced pressure, and the remaining yellow slurry was dissolved in 400 mL 1:1 CH2Cl2:H2O. The organic fraction was washed 3* with 100 mL H2O, and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to produce Diethyl-2-(1-pyrenylmethyl)-2-acetamidomalonate (14.70 g, 83.1%) as a light yellow powder. TLC (SiO2, 1:1 Hexane:EtOAc) Rf=0.57. Mp=135-140 C. 1H NMR (CDCl3), delta1.37 (t, 6H), 1.95 (s, 3H), 3.76 (s, 2H), 4.30 (q, 6H), 6.42 (s, NH), 8.00-825 (m, 9H from pyrene).

Reference： [1]Patent: US2003/144185,2003,A1

37
[ 2595-90-6 ]
[ 10016-20-3 ]
[ 913976-28-0 ]

Reference： [1]Chemistry - A European Journal,2006,vol. 12,p. 6701 - 6710

38
[ 2595-90-6 ]
[ 1006061-57-9 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 13235 - 13238
[2]New Journal of Chemistry,2018,vol. 42,p. 16542 - 16554
[3]Journal of Organic Chemistry,2008,vol. 73,p. 8212 - 8218
[4]Journal of Polymer Science, Part A: Polymer Chemistry,2014,vol. 52,p. 321 - 329
[5]Chemical Communications,2009,p. 5573 - 5575

39
[ 696-63-9 ]
[ 2595-90-6 ]
[ 1067915-18-7 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 12846 - 12847

40
[ 2595-90-6 ]
[ 108-98-5 ]
[ 1067915-12-1 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 12846 - 12847

41
[ 578-66-5 ]
[ 2595-90-6 ]
[ 1173932-11-0 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 3378 - 3381

42
[ 2595-90-6 ]
[ 130-95-0 ]
Br^(1-)*C₃₇H₃₅N₂O₂⁽¹⁺⁾ [ No CAS ]

Reference： [1]Organic Letters,2009,vol. 11,p. 4294 - 4297

43
[ 84661-56-3 ]
[ 2595-90-6 ]
[ 1189512-75-1 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 15528 - 15533

44
[ 2595-90-6 ]
[ 5466-54-6 ]
bis(1-pyrenylmethylthio)maleonitrile [ No CAS ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 1819 - 1825

45
[ 2595-90-6 ]
[ 5466-54-6 ]
[ 540-51-2 ]
1-pyrenylmethylthio-2-hydroxyethylthio-maleonitrile [ No CAS ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 1819 - 1825

46
[ 112-18-5 ]
[ 2595-90-6 ]
[ 1245501-83-0 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4014 - 4017

47
[ 524-38-9 ]
[ 2595-90-6 ]
[ 1259085-85-2 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 8651 - 8653

48
[ 2595-90-6 ]
[ 85909-08-6 ]
[ 1258509-07-7 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 17405 - 17407

49
[ 2595-90-6 ]
5-[(2-hydroxyethoxy)methyl]-5-methyl-1,4,7,10-tetraoxa-13-azacyclopentadecane [ No CAS ]
[ 1379459-85-4 ]

Reference： [1]Chemistry Letters,2011,vol. 40,p. 1226 - 1228

50
[ 2595-90-6 ]
5-[[2-(2-hydroxyethoxy)ethoxy]methyl]-5-methyl-1,4,7,10-tetraoxa-13-azacyclopentadecane [ No CAS ]
[ 1379459-49-0 ]

Reference： [1]Chemistry Letters,2011,vol. 40,p. 1226 - 1228

51
[ 2595-90-6 ]
[ 1206481-83-5 ]
2Br^(1-)*C₇₃H₈₈N₆⁽²⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In acetonitrile; for 1h;Reflux;	3alpha,7alpha-Bis[3-(1-imidazolyl)propyl]amino]-5alpha-cholestane1 (100 mg, 0.25 mmol) and <strong>[2595-90-6]1-bromomethylpyrene</strong>2 (185 mg, 0.66 mmol) was dissolved in acetonitrile (30 mL) and reflux for 1 h. After the reaction was completed, the solvent was removed under vacuum to dryness. To the residue, acetone (20 mL) was added and stirred for 20 min at room temperature. The solid precipitated was filtered; the precipitate was dissolved in CH2Cl2 and treated with hexane to give 156 mg of bromide salt 4 (80%). Mp: 175-178 oC (CH2Cl2-hexane) 1H NMR delta 0.33 (s, 3H, 18-CH3), 0.49 (s, 3H, 19-CH3), 0.76 (d, J = 6.5 Hz, 3H, 26-CH3), 0.78 (d, J = 6.5 Hz, 3H, 27-CH3), 0.85 (d, J = 6.5 Hz, 3H, 21-CH3), 2.72 (m, 4H, HNCH2CH2CH2Imi), 3.28 (bs, 1H, 7beta-H), 3.47 (bs, 1H, 3beta-H) 4.33 (m, 4H, HNCH2CH2CH2Imi), 5.28 (m, 4H, CH2-Imi), 5.88 (m, 4H, ImiCH2Py), 6.43 (bs, 1H, 7alpha-NH), 6.70 (bs, 1H, 3alpha-NH), 6.83 (s, 2H, Im H-5), 6.92 (s, 2H, Im H-4), 7.64 (s, 1H, Im H-2), 7.66-7.98 (m, 18 H, PyH); 13C NMR delta 10.7, 11.5, 11.7, 18.3, 18.4, 22.6, 22.9, 24.0, 24.3, 26.4, 26.9, 27.1, 28.0, 35.9, 37.9, 38.2, 39.3, 40.8, 42.7, 43.0, 45.6, 47.4, 51.0, 56.1, 120.9, 121.0, 121.7, 122.8, 122.9, 123.2, 123.9, 124.4, 124.9, 125.1, 125.2, 125.7, 126.2, 126.9, 127.1, 127.2, 127.4, 128.0, 128.5, 128.8, 129.2, 130.2, 130.7, 130.9, 131.8; HR-FAB MS Calcd for C73H88N6Br (M+H)+ and (M+H+2)+: 1127.6254, 1129.6256, Found: m/z 1127.6260, 1129.6267.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 6743 - 6747

52
[ 2595-90-6 ]
[ 1206481-75-5 ]
[ 1351950-66-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	In acetonitrile; for 1h;Reflux;	3alpha-[3-(1-Imidazolyl)propyl]amino-5alpha-cholestan-7-one1 (100 mg, 0.25 mmol) and <strong>[2595-90-6]1-bromomethylpyrene</strong>2 (92 mg, 0.31 mmol) was dissolved in acetonitrile (30 mL) and reflux for 1 h. After the reaction was completed, the solvent was removed under vacuum to dryness. To the residue, acetone (20 mL) was added and stirred for 20 min at room temperature. The solid precipitated was filtered; the precipitate was dissolved in CH2Cl2 and treated with hexane to give 115 mg of bromide salt 5 (80%). Mp: 155-157 oC (CH2Cl2-hexane) 1H NMR delta 0.61 (s, 3H, 18-CH3), 0.83 (d, J = 6.6 Hz, 3H, 26-CH3), 0.84 (d, J = 6.6 Hz, 3H, 27-CH3), 0.88 (d, J = 6.6 Hz, 3H, 21-CH3), 1.24 (s, 3H, 19-CH3), 2.84 (bs, 2H, HNCH2CH2CH2Imi), 3.21 (m, 2H, HNCH2CH2CH2Imi), 3.49 (bs, 1H, 3beta-H), 4.74 (bs, 2H, CH2-Imi), 5.70 (m, 2H, ImiCH2Py), 6.18 (s, 1H, Im H-5), 7.01 (s, 1H, Im H-4), 7.87 (s, 1H, Im H-2), 7.97-8.28 (m, 9H, PyH), 10.19 (bs,1H, NH); 13C NMR delta 10.7, 11.3, 12.0, 14.3, 18.6, 21.2, 22.7, 22.9, 23.0, 24.2, 25.0, 28.1, 28.3, 29.6, 29.9, 31.4, 35.6, 36.0, 36.3, 37.9, 38.4, 39.6, 40.8, 42.4, 45.6, 47.4, 48.8, 50.2, 51.0, 53.9, 54.9, 56.1, 77.4, 122.4, 124.5, 125.0, 125.2, 125.5, 126.2, 126.6, 127.4, 128.7, 129.6, 130.0, 130.6, 131.2, 132.6, 136.0, 136.5, 212.0; HR-FAB MS Calcd for C50H66N3OBr [M-Br]+: 724.5206, Found: m/z 724.5203.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 6743 - 6747

53
[ 2595-90-6 ]
[ 65-71-4 ]
[ 1383252-97-8 ]