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[ CAS No. 117241-31-3 ] {[proInfo.proName]}

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Chemical Structure| 117241-31-3
Chemical Structure| 117241-31-3
Structure of 117241-31-3 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 117241-31-3 ]

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Alternatived Products of [ 117241-31-3 ]

Product Details of [ 117241-31-3 ]

CAS No. :117241-31-3 MDL No. :MFCD31697644
Formula : C43H78O5 Boiling Point : -
Linear Structure Formula :(C6H2)(OC12H25)3COOH InChI Key :CEJSFFKDFWPORO-UHFFFAOYSA-N
M.W : 675.08 Pubchem ID :11169869
Synonyms :

Calculated chemistry of [ 117241-31-3 ]

Physicochemical Properties

Num. heavy atoms : 48
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.84
Num. rotatable bonds : 37
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 211.51
TPSA : 64.99 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : 2.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 7.86
Log Po/w (XLOGP3) : 18.11
Log Po/w (WLOGP) : 14.28
Log Po/w (MLOGP) : 7.73
Log Po/w (SILICOS-IT) : 15.22
Consensus Log Po/w : 12.64

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 3.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -13.09
Solubility : 0.0000000001 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (Ali) : -19.71
Solubility : 1.32e-17 mg/ml ; 1.96e-20 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -15.1
Solubility : 0.0 mg/ml ; 7.87e-16 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 6.04

Safety of [ 117241-31-3 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 117241-31-3 ]

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

  • Downstream synthetic route of [ 117241-31-3 ]

[ 117241-31-3 ] Synthesis Path-Downstream   1~93

  • 3
  • [ 117241-30-2 ]
  • [ 117241-31-3 ]
YieldReaction ConditionsOperation in experiment
96% With water; potassium hydroxide; In ethanol; for 2h;Reflux; Compound 2 (0.5g, 0.7mmol) and KOH (0.16 g, 2.9 mmol) were dissolved in ethanol (40 mL) and the solution was stirred under reflux for 2h. Then the solution was cooled to room temperature and acidified using 2M aq. HCl. Then the mixture was extracted with water and CH2Cl2. The organic phase was dried over Na2SO4 and was concentrated under reduced pressure. The crude product was recrystallized from ethanol and obtained compound 3 (0.46 g, 96% yield). 1H NMR (600MHz, CDCl3): δ= 7.32 (s, 2H), 4.02-4.08 (m, 6H), 1.70-1.85 (m, 6H), 1.43-1.51 (m, 6H), 1.25-1.39 (m, 48H), 0.84-0.91 (m, 9H) (Fig.S3).
91.7% Under nitrogen atmosphere, 5.22 g of potassium hydroxide and 100 ml of ethanol were added to 10.0 g of (3), and refluxed at 80C over one night, and then left to cool, and hydrochloric acid was added to the reaction mixture. When the reaction mixture turned acidic, the mixture was extracted with ether. After the ether had been evaporated, the residue was recrystallized from acetone to afford a white solid (4) (yield: 8.65 g, percent yield: 91.7%). The organic layer was dried over magnesium sulfate, the magnesium sulfate was filtered out and the organic solvent was evaporated to obtain a white solid (2).
With water; sodium hydroxide; In ethanol; for 6h;Reflux; General procedure: Compounds 9a-d were synthesized using similar procedures. A representative synthesis is described for compound 9a. An aqueous solution of NaOH (97.2 mg, 2.46 mmol, 20 mL) was added to a solution of 8a (500 mg, 1.23 mmol) in ethanol (30 mL). The reaction mixture was refluxed for 6 h. The mixture was cooled and then the ethanol was removed using a rotary evaporator. The mixture was poured onto crushed ice and acidified with concentrated HCl. The mixture was repeatedly extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated. An off-white solid was obtained by recrystallization from ethanol.
With potassium hydroxide; In 1,4-dioxane; isopropyl alcohol;Reflux; General procedure: The ethyl benzoate was dissolved in an alcohol and an excess of a sodium hydroxidesolution (2N) was added. The resulting mixture was stirred under reflux overnight. Aftercompletion, the reaction was quenched with hydrochloric acid (2N) and the suspension wasextracted three times with toluene or chloroform. The combined organic phases were driedwith MgSO4 and the solvent was removed on the rotary evaporator. The crude product waseither recrystallized or chromatographed through a column.

  • 4
  • [ 117241-31-3 ]
  • [ 117241-33-5 ]
YieldReaction ConditionsOperation in experiment
98.7% With thionyl chloride; at 80℃; for 20h;Heating / reflux; Under nitrogen atmosphere, into a flask 4.30 g of (4) and 4 ml of thionyl chloride were charged, and the mixture was refluxed at 80C for 20 hours. Thereafter, the thionyl chloride was distilled off to afford a whitish yellow solid (5) (yield: 4.36 g, percent yield: 98.7%).
With thionyl chloride; In dichloromethane; for 8h;Reflux; General Procedure: The acid chlorides were prepared by the reaction between corresponding carboxylic acids and thionyl chloride in freshly distilled dichloromethane by heating under reflux for 8 h. The excess of thionyl chloride was removed under reduced pressure and the resulting products were used in the next step without further purification. A solution of corresponding acid chloride (5 mmol) in acetone (15 mL) was added dropwise to a solution of KSCN (5 mmol) in acetone (30 mL). The resulting mixture was stirred and heated under reflux for 30 min. After the mixture was cooled down to room temperature, a solution of corresponding p-alkoxyaniline (46 mmol) in acetone (10 mL) was added dropwise for another 30 min. The mixture was further stirred at room temperature for 2 h after which 100 mL of water was added. The resulting precipitate was filtered off and washed several times with water and ethanolfollowed by recrystallisation from a mixture of dichloromethane/ethanol.
With thionyl chloride; In toluene; for 4h;Inert atmosphere; Reflux; Under the protection of nitrogen, 0.1 g of compound 5 was added to 20 mL of toluene,Then 1.5 mL was added Of thionyl chloride,The reaction was refluxed for 4 hours. Excess of thionyl chloride was removed immediately after completion of the reaction with toluene,To give compound 7, wherein the molar ratio of compound 5, thionyl chloride and toluene is 1: 5: 1000
With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane;Inert atmosphere; General procedure: To a solution of the appropriate carboxylic acid (0.57 mmol) and excess thionyl chloride (1.71 mmol; 0.12 mL) in dry CH2Cl2 (5 mL) 3 drops of dry DMF were added, and the mixture was stirred overnight under an atmosphere of Ar. The unconsumed thionyl chloride was removed under vacuum, and the resulting solid was dissolved in dry CH2Cl2. The solvent was evaporated in vacuo, and the procedure was repeated 2-3 times. The crude acyl chloride was dried under vacuum until no more odor of thionyl chloride was detected, and it was used for the next step without further purification.
With thionyl chloride; for 4h;Reflux; Synthesis of compounds of Formula II: Take intermediate compound S2 (2.8g, 4.1mmol) was dissolved in an excess of SOCl2(14mL), stirred and heated to reflux for 4 hours. After the reaction, was distilled off rotary remaining SOCl2Give the acid chloride. Take excess NaN3(2g, 30mmol) was dissolved in H2O (30mL). In an ice bath, the above acid chloride in THF (10mL) was added dropwise NaN3Aqueous solution, and the reaction was stirred at room temperature overnight. After reaction, the organic phase was extracted with dichloromethane and washed with saturated brine, dried over anhydrous Na2SO4Sulfate, and rotary evaporated to give a yellow solid. The yellow solid was dried under reduced pressure at the pump, dissolved in ultra-dry toluene (40 mL), an argon atmosphere, stirred and heated to reflux for 6 hours. After the solvent by rotary evaporation, to give a compound of formula II.
With thionyl chloride; In dichloromethane; at 20℃; for 2h;Cooling with ice; 10 ml of thionyl chloride was diluted with 20 ml of dry methylene chloride,The resulting diluted solution was added dropwise to a round bottom flask containing 7.3 g of compound 3 (10.8 mmol) and 50 ml of dry dichloromethane under ice-cooling,After being added dropwise,The mixture was stirred at room temperature for 2 hours to give compound 4,
With thionyl chloride; for 12h;Reflux; Weigh <strong>[117241-31-3]3,4,5-tris(dodecyloxy)benzoic acid</strong> (2.00 g, 2.96 mmol) in a 100 mL single-mouth eggplant bottle.After adding 30 mL of thionyl chloride, the system was refluxed for 12 h and the system was cooled to room temperature and the thionyl chloride in the system was removed.Weigh out p-iodoaniline (0.77g, 3.52mmol),1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.68 g, 3.54 mmol),4-dimethylaminopyridine (0.29 g, 2.38 mmol) was added to the system.Further, 50 mL of 1,2-dichloroethane was added as a solvent to the system, and the system was stirred at room temperature overnight.After the TLC monitors the reaction, the 1,2-dichloroethane in the systemRemove.After adding dichloromethane, the reaction solution is poured into a beaker and the reaction liquid is washed by adding distilled water, and the organic phase is combined and dried.The resulting mixture was purified using a silica gel column to afford white crystals.
With thionyl chloride; In dimethyl sulfoxide; N,N-dimethyl-formamide; for 5h;Reflux; Add the above 2) to the excess dimethyl sulfoxideThe 1 mole part of <strong>[117241-31-3]3,4,5-tris(dodecyloxy)benzoic acid</strong> and 1-2 drops of dried N,N-dimethylformamide prepared in the step were refluxed for 5 hours.The excess dimethyl sulfoxide was evaporated under reduced pressure to obtain a white solid.
With thionyl chloride; N,N-dimethyl-formamide; In toluene; for 12h;Reflux; General procedure: 10 mmol) alkoxybenzoic acid and 4 mL SOCl2 in 60 mL dry toluene with 1 drop DMF wererefluxed for 12 h. The solvent was evaporated, the residue dissolved in 20 mL dioxane andthis solution was added dropwise into 300ml heavily stirred, ice-cold, concentrated ammoniasolution. Precipitated amide and chloroform extracts were dried, concentrated, and theresidue recrystallized from toluene. Yield generally quantitative.

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  • 5
  • [ 117241-31-3 ]
  • [ 112-27-6 ]
  • 2-<2-(2-hydroxyethoxy)ethoxy>ethyl 3,4,5-tris(n-dodecan-1-yloxy)benzoate [ No CAS ]
  • 6
  • [ 123126-39-6 ]
  • [ 117241-31-3 ]
YieldReaction ConditionsOperation in experiment
97.22% Add product 1 (35.70g, 51.81mmol) to a 250mL three-necked flask, 20% sodium hydroxide solution 50ml And 100 mL of tetrahydrofuran, and the mixture was stirred at 80 degrees Celsius for 24 h. After the reaction liquid is cooled, the solvent is spin-dried under reduced pressure; the pH of the solution is adjusted to 1 with dilute hydrochloric acid; 34.00 g of the product is obtained by suction filtration, and the yield is 97.22%.
95% With potassium hydroxide; In ethanol; water; at 80℃; for 3h;Inert atmosphere; To 17 (5.00 g, 7.26 mmol) in ethanol (200 mL) heated at 80 C, potassium hydroxide (0.898 g, 16.0 mmol) in 2.5 mL of water was added. The mixture was refluxed for 3 h under a nitrogen atmosphere. After evaporating ethanol, 50 mL of 2 mol/L HCl aqueous solution was added and the mixture was extracted with diethyl ether. The combined organic layer was dried over anhydrous magnesium sulfate. After filtration, solvent in the filtrate was removed under reduced pressure to give 4.64 g (95 %) of 18 as white solid
90% With sodium hydroxide; In ethanol; water; at 20℃; for 6h; ethanol solution (30mL) of the compound S1 (4g, 6.8mmol) with an excess of aqueous NaOH solution (10 mL) were mixed and stirred at room temperature for 6 hours. After the reaction was quenched with 1M hydrochloric acid, adjusted to a pH of the reaction solution. The organic phase was extracted with dichloromethane, and dried over anhydrous Na2SO4Sulfate, and rotary evaporated to give a white solid S2 3.5g, yield about 90%.
90% Add 1 mole part of 3,4,5-tris(dodecyloxy)methyl benzoate prepared in step 1) above and 6 mole parts of potassium hydroxide to methanol (40 mL) under reflux and stir for 5 hours.Add an appropriate amount of dilute hydrochloric acid for acidification,Recrystallize with ethanol,3,4,5-tris(dodecyloxy)benzoic acid is obtained as a white solid,90% yield;
88% With potassium hydroxide; In ethanol; for 14h;Reflux; Methyl 3,4,5-tris(dodecyloxy)benzoate (6.8 g, 9.8 mmol)And potassium hydroxide (1.10g, 19.6mmol) in a 250mL three-necked flask,The system was refluxed for 14 hours after the addition of 120 mL of absolute ethanol.After the TLC monitoring reaction was completed, dilute hydrochloric acid was added to adjust the pH to 1.The reaction solution was cooled to room temperature and then filtered with suction.
76% With water; potassium hydroxide; In ethanol; for 2h; In a 500 mL round bottom flask,With 250ml of anhydrous ethanol and10 mL of deionized water heated to reflux10 g of compound 2 (14.5 mmol)With an excess of potassium hydroxide (2.8 g, 50 mmol)The mixture was stirred for 2 hours.After the end of the reaction, the solution was cooled to room temperature, the solution was transferred to acid and dissolved in 1 L of deionized water.A large amount of white precipitate is instantly produced, decompressed and filtered to collect the filter cake to obtain the crude product.The crude product was recrystallized from acetone three times to give pure white solid product compound 3 (7.8 g, yield 76%).
With ethanol; potassium hydroxide; at 80℃; for 8h; 0.5 g of compound 4 was dissolved in 17 mL of ethanol, and then 0.4 g of potassium hydroxide was added, and the mixture was stirred at 80 CThe mixture was stirred at reflux for 8 hours, and the solution was diluted with water and acidified to pH = 1 with 1 mol / L hydrochloric acid. The white precipitateFiltered, washed with water three times and dried to give compound 5. & lt; Of compound 4, potassium hydroxide and ethanolRatio of 1: 2: 380.

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  • 8
  • [ 125358-20-5 ]
  • [ 117241-31-3 ]
  • (2E)-2,3-bis[(trimethylsilyl)ethynyl]but-2-ene-1,4-diyl bis[3,4,5-tris(dodecyloxy)benzoate] [ No CAS ]
  • 10
  • [ 117241-31-3 ]
  • [ 222639-34-1 ]
  • 2,5-bis[4-(3,4,5-tridodecyloxyphenylcarbonyloxy)phenylethynyl]-3,4-dicyanothiophene [ No CAS ]
  • 11
  • [ 117241-31-3 ]
  • [ 336884-81-2 ]
  • [ 336884-82-3 ]
  • 12
  • [ 6066-82-6 ]
  • [ 117241-31-3 ]
  • [ 380441-58-7 ]
YieldReaction ConditionsOperation in experiment
With N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; GA12-NHS was synthesized according to a modification of a published method.2 GA12OH (1g,1.3mmol), N,N’-dicyclohexylcarbodiimide (0.347g, 1.7mmol) and N-hydroxysuccinimide(0.194g, 1.7mmol) were dissolved in 50 mL dichloromethane followed by addition of catalyticamount of DMF. The solution was stirred at room temperature overnight. The crude material waspurified by silica gel column chromatography using hexane and EtOAc (4/1).1H NMR (400MHz, CDCl3): δ 7.32 (s, 2H), 4.07-3.99 (m, 6H), 2.92-2.89 (m, 4H), 1.85-1.78 (m,4H), 1.75-1.70 (m, 2H), 1.50-1.43 (m, 6H), 1.36-1.26 (m, 48H), 0.89-0.86 (m, 9H)
  • 13
  • [ 117241-31-3 ]
  • C86H154O9 [ No CAS ]
  • 14
  • [ 2493-84-7 ]
  • [ 117241-31-3 ]
  • [ 222639-34-1 ]
  • 2,5-bis[4-(3,4,5-tridodecyloxyphenylcarbonyloxy)phenylethynyl]-3,4-dicyanothiophene [ No CAS ]
  • C52H50N2O6S [ No CAS ]
  • 2-[4-(3,4,5-tridodecyloxyphenylcarbonyloxy)phenylethynyl]-5-[4-(4-octyloxyphenylcarbonyloxy)phenylethynyl]-3,4-dicyanothiophene [ No CAS ]
  • 16
  • [ 117241-31-3 ]
  • [ 755758-56-6 ]
  • (2E)-2-[(triisopropylsilyl)ethynyl]but-2-ene-1,4-diyl bis[3,4,5-tris(dodecyloxy)benzoate] [ No CAS ]
  • 17
  • [ 117241-31-3 ]
  • [ 368886-52-6 ]
  • C107H188O18 [ No CAS ]
  • 18
  • [ 117241-31-3 ]
  • 3,4,5-tris-dodecyloxy-benzoyl fluoride [ No CAS ]
  • 19
  • [ 109073-77-0 ]
  • [ 117241-31-3 ]
  • [ 859839-18-2 ]
  • 21
  • [ 880131-73-7 ]
  • [ 117241-31-3 ]
  • [ 880131-74-8 ]
  • 22
  • [ 117241-31-3 ]
  • [ 882054-68-4 ]
  • C182H318O16 [ No CAS ]
  • 23
  • [ 63826-59-5 ]
  • [ 117241-31-3 ]
  • 3,4,5-tris-dodecyloxy-benzoic acid 5-methyl-thiophen-2-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide
  • 24
  • [ 6287-90-7 ]
  • [ 117241-31-3 ]
  • 10-methoxycarbonyldecyl 3,4,5-tris-dodecyloxybenzoate [ No CAS ]
  • 25
  • [ 2563-26-0 ]
  • [ 117241-31-3 ]
  • 4,5-dibromo-2-[3,4,5-tris(dodecyloxy)benzoyl]oxy}phenyl 3,4,5-tris(dodecyloxy)benzoate [ No CAS ]
  • 26
  • [ 75937-12-1 ]
  • [ 117241-31-3 ]
  • 6-tert-butoxycarbonylaminohexyl 3,4,5-tris-dodecyloxybenzoate [ No CAS ]
  • 27
  • [ 120-80-9 ]
  • [ 117241-31-3 ]
  • 2-[3,4,5-tris(dodecyloxy)benzoyl]oxy}phenyl 3,4,5-tris(dodecyloxy)benzoate [ No CAS ]
  • 28
  • [ 117241-31-3 ]
  • [ 151237-05-7 ]
  • N-<3,4,5-tris(n-dodecan-1-yloxy)phenyl>-3,4,5-tris(n-dodecan-1-yloxy)benzamide [ No CAS ]
  • 30
  • [ 117241-31-3 ]
  • [ 102522-47-4 ]
  • [ 1032944-74-3 ]
  • 31
  • [ 678-39-7 ]
  • [ 117241-31-3 ]
  • 1H,1H,2H,2H-heptadecafluoro-1-decyl 3,4,5-tri(dodecyloxy)benzoate [ No CAS ]
  • 32
  • [ 99-24-1 ]
  • [ 117241-31-3 ]
Reference: [1]Tetrahedron Letters,2007,vol. 48,p. 6330 - 6333
[2]Chemistry - A European Journal,2007,vol. 13,p. 4155 - 4162
[3]Journal of the American Chemical Society,2005,vol. 127,p. 14980 - 14981
[4]Journal of the American Chemical Society,2005,vol. 127,p. 888 - 903
[5]Organic Letters,2004,vol. 6,p. 2495 - 2497
[6]Journal of Materials Chemistry,2004,vol. 14,p. 1722 - 1730
[7]Chemistry - A European Journal,1999,vol. 5,p. 1070 - 1083
[8]Journal of Materials Chemistry,1998,vol. 8,p. 331 - 341
[9]Journal of the Chemical Society, Dalton Transactions,1997,p. 4683 - 4687
[10]Chemistry - A European Journal,1997,vol. 3,p. 300 - 307
[11]Chemistry - A European Journal,2011,vol. 17,p. 546 - 556
[12]Journal of Molecular Structure,2011,vol. 987,p. 1 - 6
[13]Chemical Communications,2011,vol. 47,p. 5702 - 5704
[14]Soft Matter,2010,vol. 6,p. 3195 - 3201
[15]Bulletin of the Chemical Society of Japan,2012,vol. 85,p. 236 - 244
[16]Journal of the American Chemical Society,2013,vol. 135,p. 9055 - 9077
[17]Molecular Crystals and Liquid Crystals,2013,vol. 577,p. 25 - 35
[18]Chemistry - A European Journal,2013,vol. 19,p. 12991 - 13001
[19]Dyes and Pigments,2014,vol. 101,p. 74 - 84
[20]New Journal of Chemistry,2015,vol. 39,p. 72 - 76
[21]Crystal Growth and Design,2015,vol. 15,p. 900 - 906
[22]Chemical Communications,2015,vol. 51,p. 6512 - 6514
[23]Angewandte Chemie - International Edition,2015,vol. 54,p. 2543 - 2547
    Angew. Chem.,2015,vol. 127,p. 2573 - 2577,5
[24]Journal of Organic Chemistry,2014,vol. 79,p. 8366 - 8373
[25]Chemistry - A European Journal,2016,vol. 22,p. 15772 - 15777
[26]Patent: CN105906624,2016,A
[27]Bulletin of the Chemical Society of Japan,2017,vol. 90,p. 298 - 305
[28]Patent: CN106632382,2017,A
[29]Patent: CN106946732,2017,A
[30]Journal of Materials Chemistry C,2017,vol. 5,p. 9165 - 9173
[31]Chemistry of Materials,2017,vol. 29,p. 8737 - 8746
[32]Journal of Materials Chemistry C,2017,vol. 5,p. 5465 - 5477
[33]Langmuir,2019,vol. 35,p. 1598 - 1605
[34]Bioorganic and Medicinal Chemistry,2018,p. 5307 - 5313
[35]Journal of the American Chemical Society,2019,vol. 141,p. 5635 - 5639
[36]Patent: CN109485582,2019,A
[37]Journal of the American Chemical Society,2019,vol. 141,p. 7385 - 7390
[38]Chemistry - A European Journal,2019,vol. 25,p. 15401 - 15410
[39]Chinese Journal of Chemistry,2012,vol. 30,p. 2085 - 2090,6
[40]Patent: CN111662196,2020,A
[41]Chemical Communications,2021,vol. 57,p. 911 - 914
[42]Angewandte Chemie - International Edition,2021,vol. 60,p. 7851 - 7859
    Angew. Chem.,2021,vol. 133,p. 7930 - 7938,9
[43]Patent: CN112920224,2021,A
[44]Journal of the American Chemical Society,2021,vol. 143,p. 13281 - 13291
[45]Journal of the American Chemical Society,2021,vol. 143,p. 14136 - 14146
  • 33
  • [ 143-15-7 ]
  • [ 117241-31-3 ]
Reference: [1]Tetrahedron Letters,2007,vol. 48,p. 6330 - 6333
[2]Chemistry - A European Journal,2007,vol. 13,p. 4155 - 4162
[3]Chemistry - A European Journal,2006,vol. 12,p. 763 - 776
[4]Chemical Communications,2005,p. 4149 - 4151
[5]Chemistry - A European Journal,2006,vol. 12,p. 8396 - 8413
[6]Tetrahedron,2006,vol. 62,p. 9681 - 9687
[7]Angewandte Chemie - International Edition,2005,vol. 44,p. 4739 - 4745
[8]Journal of the American Chemical Society,2005,vol. 127,p. 14980 - 14981
[9]Journal of the American Chemical Society,2005,vol. 127,p. 888 - 903
[10]Organic Letters,2004,vol. 6,p. 2495 - 2497
[11]Journal of Materials Chemistry,2004,vol. 14,p. 1722 - 1730
[12]Chemistry - A European Journal,1999,vol. 5,p. 1070 - 1083
[13]Zeitschrift fur Naturforschung, B: Chemical Sciences,1988,vol. 43,p. 889 - 896
[14]Chemistry - A European Journal,2011,vol. 17,p. 546 - 556
[15]Journal of Molecular Structure,2011,vol. 987,p. 1 - 6
[16]Chemical Communications,2011,vol. 47,p. 5702 - 5704
[17]Chemistry Letters,2010,vol. 39,p. 714 - 716
[18]Soft Matter,2010,vol. 6,p. 3195 - 3201
[19]Chemical Communications,2012,vol. 48,p. 877 - 879
[20]Bulletin of the Chemical Society of Japan,2012,vol. 85,p. 236 - 244
[21]Chemistry - A European Journal,2013,vol. 19,p. 12991 - 13001
[22]Dyes and Pigments,2014,vol. 101,p. 74 - 84
[23]New Journal of Chemistry,2015,vol. 39,p. 72 - 76
[24]Chemical Communications,2015,vol. 51,p. 6512 - 6514
[25]Angewandte Chemie - International Edition,2015,vol. 54,p. 2543 - 2547
    Angew. Chem.,2015,vol. 127,p. 2573 - 2577,5
[26]Chemistry - A European Journal,2016,vol. 22,p. 15772 - 15777
[27]Patent: CN105906624,2016,A
[28]Bulletin of the Chemical Society of Japan,2017,vol. 90,p. 298 - 305
[29]Patent: CN106632382,2017,A
[30]Patent: CN106946732,2017,A
[31]Journal of Materials Chemistry C,2017,vol. 5,p. 9165 - 9173
[32]Chemistry of Materials,2017,vol. 29,p. 8737 - 8746
[33]Journal of Materials Chemistry C,2017,vol. 5,p. 5465 - 5477
[34]Langmuir,2019,vol. 35,p. 1598 - 1605
[35]Journal of the American Chemical Society,2019,vol. 141,p. 5635 - 5639
[36]Patent: CN109485582,2019,A
[37]Journal of the American Chemical Society,2019,vol. 141,p. 7385 - 7390
[38]Chemistry - A European Journal,2019,vol. 25,p. 15401 - 15410
[39]Chinese Journal of Chemistry,2012,vol. 30,p. 2085 - 2090,6
[40]Chemical Communications,2021,vol. 57,p. 911 - 914
[41]Angewandte Chemie - International Edition,2021,vol. 60,p. 7851 - 7859
    Angew. Chem.,2021,vol. 133,p. 7930 - 7938,9
[42]Patent: CN112920224,2021,A
[43]Molecules,2020,vol. 25
[44]Journal of the American Chemical Society,2021,vol. 143,p. 14136 - 14146
  • 38
  • [ 117241-31-3 ]
  • [2,2']bi[[1,3]dithiolylidene]-4-carboxylic acid [2-(3,4,5-tris-dodecyloxy-benzoylamino)-ethyl]-amide [ No CAS ]
  • 41
  • [ 117241-31-3 ]
  • 2-(3-(3,4,5-trisdodecyloxyphenyl)uryl)-4-methylpyridine [ No CAS ]
  • 44
  • [ 117241-31-3 ]
  • [ 100-79-8 ]
  • C49H88O7 [ No CAS ]
  • 45
  • [ 2273-43-0 ]
  • [ 117241-31-3 ]
  • Sn6O6(12+)*6C4H9(1-)*6O2CC6H2(OC12H25)3(1-)=[(C4H9SnO(O2CC6H2(OC12H25)3))6] [ No CAS ]
  • 46
  • N,N'-bis(n-butyl)-1,6,7,12-tetrakis(4-hydroxyphenoxy)perylene-3,4,9,10-tetracarboxylic acid diimide [ No CAS ]
  • [ 117241-31-3 ]
  • N,N'-dibutyl-1,6,7,12-tetrakis(4-[3,4,5-tridodecyloxybenzoyloxy]phenoxy)perylene-3,4:9,10-tetracarboxylic acid bisimide [ No CAS ]
  • 47
  • [ 1061610-17-0 ]
  • [ 117241-31-3 ]
  • [ 949464-53-3 ]
  • 48
  • [ 84-60-6 ]
  • [ 117241-31-3 ]
  • [ 1079900-68-7 ]
  • 49
  • [ 2799-16-8 ]
  • [ 117241-31-3 ]
  • [ 1227291-48-6 ]
  • 52
  • [ 57260-73-8 ]
  • [ 117241-31-3 ]
  • [ 1304141-92-1 ]
  • 53
  • [ 117241-31-3 ]
  • [ 138433-00-8 ]
YieldReaction ConditionsOperation in experiment
95% With lithium aluminium tetrahydride; In diethyl ether; at 20℃; for 0.5h;Inert atmosphere; To lithium aluminum hydride (0.828 g, 21.8 mmol) dispersed in diethyl ether (70 mL), 18 (10.0 g, 14.5 mmol) in diethyl ether (75 mL) was added dropwise, and the mixture was stirred at ambient temperature for 30 min under a nitrogen atmosphere. To the reaction mixture, methanol (10 mL) and then 2 mol/L HCl aqueous solution (10 mL) were added, and the mixture was extracted with diethyl ether. The combined organic layer was dried over anhydrous magnesium sulfate. After filtration, solvent in the filtrate after filtration was evaporated to give 9.09 g (95 %) of 23 as white solid
  • 55
  • [ 54258-41-2 ]
  • [ 117241-31-3 ]
  • [ 1338056-16-8 ]
  • 56
  • [ 1167422-41-4 ]
  • [ 117241-31-3 ]
  • [ 1442741-24-3 ]
  • 57
  • [ 104274-80-8 ]
  • [ 117241-31-3 ]
  • [ 1442741-88-9 ]
YieldReaction ConditionsOperation in experiment
93% With dicyclohexyl-carbodiimide; 4-(dimethylamino)pyridinium tosylate; In dichloromethane; at 20℃; for 12h;Inert atmosphere; Into a solution of 13 (0.70 g, 3.76 mmol), 4c (5.33 g, 7.90 mmol), and DPTS (1.11 g, 3.76 mmol) in anhydrous CH2CI2 (13 mL) was added the solution of DCC (2.02 g, 9.78 mmol) in CH2CI2 (2 mL) in one portion at room temperature under nitrogen atmosphere. The reaction mixture was allowed to stir at room temperature for 12 h. The reaction mixture was diluted with Et20, filtered off the urea, and washed with Et20. The filtrate was concentrated and purified by column chromatography (S1O2, 0 - 5% EtOAc:hexane) to give a product as a white solid (5.27 g, 93%). 'H NMR (500 MHz, CDC13) δ 7.22 (s, 4H, 2ArH-2,6), 4.36 (s, 4Η, 2ArC02CH2), 4.00 (m, 12Η, 6ArOCH2), 3.57 (s, 4Η, 2CH2N3), 1.79 (m, 12Η, 6ArOCH2CH2), 1.47 (m, 12Η, 6ArOCH2CH2CH2), 1.26 (m, 96Η, 6(CH2)8CH3), 0.88 (t, J = 6.8, 18H, 6CH3). 13C NMR (126 MHz, CDCI3) δ 165.9 (C=0), 153.1 (ArC-3,5), 143.2 (ArC-1), 123.9 (ArC-2,6), 108.4 (ArC-4), 73.7 (ArOCH2), 69.5 (ArOCH2), 63.5 (ArC02CH2), 52.1 (CH2N3), 44.0 (C(CH2N3)2), 32.1 (CH2CH2CH3), 30.1, 29.86, 29.82, 29.80, 29.7, 29.59, 29.52, 29.50, 26.3, 26.2, 22.8 (CH2CH3), 14.3 (CH3). MALDI-TOF (m/z): [M+Na]+ calcd for C9iH162N6NaOio, 1522.23; found 1522.29.
  • 58
  • [ 2425-41-4 ]
  • [ 117241-31-3 ]
  • [ 1235584-44-7 ]
YieldReaction ConditionsOperation in experiment
90% With dicyclohexyl-carbodiimide; 4-(dimethylamino)pyridinium tosylate; In dichloromethane; at 20℃; for 12h;Inert atmosphere; The monobenzalpentaerythritol (3.64 g, 16.3 mmol), (3,4,5)12G1-C02H (5c) (24.14 g, 35.8 mmol), and DPTS (4.78 g, 16.3 mmol) were dissolved in anhydrous CH2C12 (60 mL). DCC (8.72 g, 42.3 mmol) dissolved in anhydrous CH2C12 (10 mL) was added and the reaction was stirred for 12 h at room temperature under nitrogen atmosphere. After the reaction was complete, the mixture was diluted, filtered, and rinsed with Et20. The solvent was removed and the crude product was purified by column chromatography (Si02, 10% Et20:hexane), followed by precipitation in MeOH to give a white solid as a product: 23.35 g (90%). NMR (500 MHz, CDC13) delta 7.53 - 7.48 (m, 2H, PhH-3, 5), 7.41 - 7.35 (m, 3Eta, PhH-2, 4, 6), 7.22 (s, 2Eta, ArH-2, 6), 7.22 (s, 2Eta, 2ArH-2', 6'), 5.51 (s, 1Eta, CH-acetal), 4.83 (s, 2Eta, ArC02CH2), 4.32 (d, J= 1 1.6 Hz, 2H, 20CHaHb-ring), 4.24 (s, 2H, ArC02CH2), 4.05 - 3.93 (m, 14Eta, 6ArOCH2, 20CHaHb-ring), 1.79 (m, 12Eta, 6ArOCH2CH2), 1.52 - 1.43 (m, 12Eta, 6ArOCH2CH2CH2), 1.26 (m, 96Eta, 6(CH2)8CH3), 0.88 (t, J= 6.7 Hz, 18H, 6CH3). 13C NMR (126 MHz, CDC13) delta 166.2 (C=0), 166.1 (C=0'), 153.1 (ArC-3, 5), 153.0 (ArC-3 ', 5'), 143.1 (ArC- 4), 142.9 (ArC-4'), 137.8 (PhC-1), 129.4 (PhC-3, 5), 128.6 (PhC-4), 126.3 (PhC-2, 6), 124.5 (ArC-1), 124.0 (ArC-1 '), 108.3 (ArC-2, 6), 108.2 (ArC-2', 6'), 102.5 (CH-acetal), 73.71 (ArOCH2-4), 73.67 (ArOCH2-4'), 70.1 (OC-ring), 69.40 (ArOCH2-3, 5), 69.38 (ArOCH2-3 5'), 64.0 (ArC02CH2), 63.2 (ArC02CH2'), 38.1 (C(CH20)4), 32.1 (CH2CH2CH3), 30.5 (CH2CH2CH3), 29.90, 29.88, 29.86, 29.85, 29.80, 29.7, 29.6, 29.54, 29.52, 29.50, 26.28, 26.27, 26.22 , 22.8 (CH2CH3), 14.3 (CH3). The spectroscopic data of 16c are in agreement with those previously reported
  • 59
  • [ 14235-81-5 ]
  • [ 117241-31-3 ]
  • [ 1166917-93-6 ]
  • 61
  • (2-(4-aminophenyl)ethene-1,1,2-triyl)tribenzene [ No CAS ]
  • [ 117241-31-3 ]
  • [ 1492771-29-5 ]
YieldReaction ConditionsOperation in experiment
92.8% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; for 72h;Inert atmosphere; To P4NH2 (0.18 g, 0.52 mmol) and 3 (0.42 g, 6 mmol) in THF (50 mL), DMAP (0.01 g) and EDC-HCl (0.01 g) were added. The mixture was stirred for 3 days under an argon atmosphere at room temperature. Excess ethanol was added and the resulting precipitate was collected. Then crystallized from THF and ethanol mixture for 3 times to obtain P4 as a white solid (0.48 g, yield 92.8%). Melting point: ∼78 C (DSC). 1H NMR (300 MHz, CDCl3) δ (ppm): 0.89 (t, J=6.3 Hz, 9H), 1.20-1.48 (m, 52H), 1.68-1.93 (m, 8H), 3.96-4.07 (m, 6H), 6.96-7.17 (m, 19H), 7.36 (d, J=8.4 Hz, 2H), 7.59 (s, 1H). 13C NMR (CDCl3, 75 MHz) δ (ppm): 165.6, 153.3, 143.8, 141.5, 141.0, 140.4, 140.1, 136.4, 131.5, 130.1, 127.8, 126.7, 126.6, 119.3, 105.8, 73.8, 69.7, 32.3, 30.1,29.7, 26.5, 23.1, 14.5. FT-IR (KBr) υ (cm-1): 3306, 2921, 2849, 1640, 1580, 1527, 1497, 1467, 1335, 1233, 1113, 748, 699. MS (EI), m/z: 1004 ([M]+, calcd for C69H97NO4, 1004). Anal. calcd for C69H97NO4: C 82.50, H 9.73, N 1.39; Found: C 82.44, H 9.81, N 1.32.
  • 62
  • [ 1492771-69-3 ]
  • [ 117241-31-3 ]
  • [ 1492771-89-7 ]
YieldReaction ConditionsOperation in experiment
81.6% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; for 72h; P5NH2 (0.30 g, 1.01 mmol) and 3 (0.98 g, 14.2 mmol) were dissolved in THF (50 mL), and then EDC-HCl (0.01 g) and DMAP (0.01 g) were added. The solution was stirred at room temperature for 3 days. After removing the solvent under reduced pressure, the residue was crystallized from ethanol to give white crystalline powder P5 (0.62 g, 81.6% yield). Melting point: 127-129 C (DSC). 1H NMR (300 MHz, CDCl3) δ (ppm): 0.89 (t, J=5.1 Hz, 9H), 1.16-1.47 (m, 54H), 1.70-1.90 (m, 6H), 3.98-4.09 (m, 6H), 7.10-7.16 (m, 18H), 7.31-7.38 (d, J=8.4 Hz, 2H), 7.53-7.58 (d, J=8.7 Hz, 2H), 7.62-7.57 (d, J=6.9 Hz, 2H) 7.72-7.76 (s, 1H); 13C NMR (CDCl3, 75 MHz) δ (ppm): 165.7, 153.4, 143.8, 142.8, 141.8, 140.7, 138.2, 137.4, 136.9, 132.0, 131.5, 130.1, 126.7, 126.1, 120.4, 106.1, 73.9, 69.8, 32.3, 30.4, 29.7, 26.4, 23.0, 14.5. FT-IR (KBr) υ(cm-1): 3306, 2921, 2849, 1640, 1580, 1527, 1497, 1467, 1335, 1233, 1113, 748, 699. MS (EI) calcd for C75H101NO4 1081, found 1081. Anal. calcd for C75H101NO4: C 83.36, H 9.42, N 1.30; Found: C 83.41, H 9.57, N 1.24.
  • 63
  • [ 6705-67-5 ]
  • [ 117241-31-3 ]
  • [ 1656284-61-5 ]
  • 64
  • 3,3',6,6'-tetrakis(hydroxymethyl)dibenzo-24-crown-8 [ No CAS ]
  • [ 117241-31-3 ]
  • 3,3',6,6'-tetrakis[3'',4'',5''-tri(n-dodecyloxy)benzoxymethyl]-dibenzo-24-crown-8 [ No CAS ]
  • 65
  • [ 137763-06-5 ]
  • 1-isocyano-5-(4'-cyanobiphenyl-4-oxy)pentane [ No CAS ]
  • [ 117241-31-3 ]
  • 1-(5-(4'-cyanobiphenyl-4-oxy)pentylaminocarbonyl)-6-(4'-cyanobiphenyl-4-oxy)hexyl 3,4,5-tridodecyloxybenzoate [ No CAS ]
  • 67
  • [ 351437-96-2 ]
  • [ 117241-31-3 ]
  • C27H18N6*3C43H78O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 1,3,5-tris(1H-benzo[d]imidazol-2-yl)benzene In methanol for 1h; Reflux; Stage #2: 3,4,5-tridodecyloxy benzoic acid In methanol; chloroform for 4h; Reflux;
  • 68
  • [ 5981-09-9 ]
  • [ 117241-31-3 ]
  • C147H246N4O12 [ No CAS ]
  • 69
  • 9-bromo-10-aminomethylanthracene hydrochloride [ No CAS ]
  • [ 117241-31-3 ]
  • C58H88BrNO4 [ No CAS ]
  • 70
  • [ 540-38-5 ]
  • [ 117241-31-3 ]
  • [ 1221119-75-0 ]
  • 71
  • [ 99-24-1 ]
  • [ 143-15-7 ]
  • [ 117241-31-3 ]
YieldReaction ConditionsOperation in experiment
63% (1) Methyl gallate (3.68 g, 20 mmol) and anhydrous K2CO3 (24.8 g, 180 mmol) were added to 100 mL of CH3CN, and with stirring, the compound n-dodecyl bromide (28.7 mL, 120 mmol) was added. The mixture was heated to reflux and checked by TLC until the reaction was complete (about 24 h).Stop heating, cool naturally, suction filter to remove insoluble matter. The CH3CN was removed by rotary evaporation to give a yellow viscous material. 150 mL of CH3OH was added to dissolve it. Under stirring, aqueous NaOH (2.0 g, 50 mmol, 2 mol.L-1) was added, and the mixture was heated under reflux and detected by TLC until the reaction was complete (about 2 h). The reaction was stopped, and after cooling, CH3OH was removed by rotary evaporation, and dilute acid was added to adjust the pH to acidic. Then it was poured into crushed ice, cooled to precipitate a white solid, after suction filtration, washing (water: methanol = 1:1), drying to obtain the above synthetic route of compound 1a pure product, white solid 8.5g, yield 63%;
63% With potassium carbonate; In acetonitrile; for 24h;Heating; (1) Methyl gallate (3.68 g, 20 mmol) and anhydrous K2CO3(24.8g, 180mmol) was added to 100mL CH3CN,With stirring, the compound bromo-n-dodecane was added (28.7 mL, 120 mmol). Heating back, TLC testing, Until the reaction is complete (about 24 hours). Stop heating, cool naturally,Insoluble matter was removed by suction filtration. The CH3CN was removed by rotary evaporation to give a yellow viscous material.Add 150 mL of CH3OH to dissolve it, and stir it.Add NaOH aqueous solution (2.0 g, 50 mmol, 2 mol L-1),Heat to reflux and TLC detection until the reaction was complete (about 2 hours).The reaction was stopped, and after cooling, CH3OH was removed by steaming, and the pH was adjusted to be acidic with dilute acid.Then pour it into crushed ice, cool and precipitate a white solid, and suction filtration,Washing (water: methanol = 1:1), drying to obtain a pure compound 1,White solid 8.5g, yield 63%
  • 72
  • [ 117241-31-3 ]
  • [ 151237-01-3 ]
YieldReaction ConditionsOperation in experiment
92% With 2,2'-azobis(isobutyronitrile); nitric acid; In acetonitrile; at 50℃; for 21h;Inert atmosphere; To 18 (0.500 g, 0.726 mmol) in acetonitrile (10 mL), conc. nitric acid (0.229 g, 2.18 mmol) and azobisisobutyronitrile (AIBN) (2.50 mg, 0.0152 mmol) were added and they were stirred at 50 C for 21 h under a nitrogen atmosphere. The reaction mixture was poured into iced water, and the mixture was extracted with diethyl ether. The combined organic layer was dried over anhydrous sodium sulfate. After filtration, solvent of the filtrate was evaporated under reduced pressure, and the residual solid was purified by column chromatography (silica gel, chloroform-ethyl acetate (9:1)) to give 0.450 g (92 %) of 20 as white solid
  • 73
  • [ 15252-45-6 ]
  • [ 117241-31-3 ]
  • 3,4,5-tri(dodecyloxy)-N-(5-hexynyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 6h;Inert atmosphere; To 18 (1.98 g, 2.93mmol) in dichloromethane (50 mL), 9 (0.430 g, 4.44 mmol) and N,N'-dicyclohexylcarbodiimide (DCC) (0.917 g, 4.44 mmol) were added. The mixture was stirred at ambient temperature for 6 h under a nitrogen atmosphere. After filtration, solvent in the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel, chloroform) to give 0.670 g (30 %) of 19 as white solid
  • 74
  • [ 7770-45-8 ]
  • [ 117241-31-3 ]
  • C54H84O6 [ No CAS ]
  • 75
  • C57H39N6O9P3 [ No CAS ]
  • [ 117241-31-3 ]
  • C186H267N6O21P3 [ No CAS ]
  • 76
  • C57H48N3O9P3 [ No CAS ]
  • [ 117241-31-3 ]
  • C186H276N3O21P3 [ No CAS ]
  • 77
  • [ 117241-31-3 ]
  • [ 106-50-3 ]
  • C49H84N2O4 [ No CAS ]
  • 78
  • (3,4,5-tris(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenyl)formic acid [ No CAS ]
  • [ 117241-31-3 ]
  • [ 19333-10-9 ]
  • C103H140N8O19Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% In diethylene glycol dimethyl ether; for 6h;Reflux; Inert atmosphere; SiPcCl2 (85% dye content, 150mg, 0 .245mmoi), 3,4,5 -tris(dodecyloxy)benzoic acid (827mg, 1 .23mmol), and 3,4,5-tris(methoxy(triethylenoxy))benzoic acid (746 mg, 1.23 mmoi) weredissolved in 4mL of 2-methoxyethyl ether in a pre-dried flask. The reaction was refluxed for6 hours under argon atmosphere. After cooling down to room temperature, the solvent wasevaporated under vacuum. The remaining slurry solid was purified by column chromatography on silica gel, using DCM and then a gradient of DCM/MeOH, from 60:1 to 30:1, as eluent. The central fraction, corresponding to the final product, was collected and the solvent evaporated to yield the pure compound as a gummy blue solid (120mg, 0.O66mmol,27%).Mp.: 115CTransition temperature (to liquid crystal mesophase): 56.53 C.1H NMR (300 MHz, CDC13), 6 (ppm): 9.72 (m, 8H, Hp), 8.40(m, 8H, Hp), 4.21 (s, 2H,H), 4.19 (s, 2H, HAT), 3,74 (m, 2H), 3.68 (m, 4H), 3.61 (m, 2H), 3.56 (m, 4H), 3.50 (m, 4H),3.44 (m, 1OH), 3.38 (4H), 3.34 (m, 2H), 3.31 (m, 9H, CH3), 3.28 (m, 4H, OCH2), 3.26 (s, 4H),3.0 (t, J= 4.5 Hz, 4H, OCH2), 2.84 (t, J= 6.1 Hz, 4H, OCH2), 1,18 (m, 66H, CH2), 0.87 (m,9H, CH3)3C NMR (300 MHz, CDC13), 6 (ppm): 158.94, 158.75, 151.04, 150.54, 150.19, 140.15,140.01, 135.53, 131.46, 125.30, 124.95, 124.07, 105.69, 105.04, 72.82, 71.87, 71.79, 71.71,70.52, 70.54, 70.32, 70.20, 70.09, 69.10, 67.69, 67.45, 31.93, 31.88, 29.87, 29.69, 29.66,29.60, 29.58, 29.55, 29.52, 29.36, 29.30, 29.20, 28.80, 25.78, 25.70, 22.69, 22.65, 14.12,14.07FT4R (film), v (cm1): 2922, 2852, 1729, 1635, 1430, 1384, 1336, 1123, 1083, 914, 762, 737UV/Vis (CHC13), )max (nm) (log ): 686 (5.4), 655 (4.48), 617 (4.55), 360 (4.8)HRMS (MALDITOF, DCTB + PPGNa 2000), rn/z: Calc. for C103H140N8O19Si: 1822.0029, found 1822.0035 [Mj
  • 79
  • [ 1616780-44-9 ]
  • [ 117241-31-3 ]
  • C43H78O5*C13H12N2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at 25℃; for 0.5h; General procedure: Complexes 1-4 were all prepared using the same procedure. A representative synthesisis described for 1. Compound 9a (50.0 mg, 0.132 mmol) and 4-(2,2’-bithiophen-5-yl)-3,5-dimethyl-1H-pyrazole (34.4 mg, 0.132 mmol) were dissolved in anhydrous THF and the solution was stirred for 30 min at 25 C. The solvent was removed using a rotary evaporator to yield 1 as a pale-yellow solid.
  • 80
  • [ 26690-80-2 ]
  • [ 117241-31-3 ]
  • 2-((tert-butoxycarbonyl)amino)ethyl 3,4,5-tris(dodecyloxy)benzoate [ No CAS ]
  • 81
  • [ 14444-02-1 ]
  • [ 117241-31-3 ]
  • C67H92N2O6 [ No CAS ]
  • 82
  • [ 57260-73-8 ]
  • [ 117241-31-3 ]
  • [ 912275-84-4 ]
YieldReaction ConditionsOperation in experiment
87% (2) Compound 1a (6.75 g, 10 mmol), EDCI (2.11 g, 11 mmol), HOBt (1.49 g, 11 mmol) was added to 100 mL of CH2Cl2 and stirred at room temperature for 30 min; N-Boc-ethylenediamine (1.76 g) was added. (11 mmol) was dissolved in 20 mL of CH2Cl2 and added dropwise to the above reaction mixture, stirring at room temperature was continued, TLC detection until the reaction was complete (about 10 h). The reaction was stopped, and dilute acid was added to adjust the pH to acidic. The mixture was transferred to a separatory funnel, and the layers were separated. The organic layer was washed with H2O (100 mL×2) and saturated brine (100 mL×1) successively, and then dried over anhydrous Na 2 SO 4 . The organic solvent was distilled off under reduced pressure to give a yellow viscous liquid. 20 mL of CH2Cl2 was added to dissolve the mixture. Under stirring, CF3COOH (10 mL) was added, and the mixture was heated under reflux and checked by TLC until the reaction was complete (about 2 h). The heating was stopped, and after cooling to room temperature, Et3N was slowly added and the system was adjusted to be slightly alkaline. The reaction solution was transferred to a separating funnel, washed successively with water (50 mL×3), saturated brine (50 mL×1), and the organic layer was dried over anhydrous Na 2 SO 4 . The organic solvent was spin-dried, and the crude product was separated by column chromatography (CH2Cl2:CH3OH=20:1) to give the pure product of compound 2a as a white solid 6.2 g, yield 87%;
87% (2) Compound 1 (6.75 g, 10 mmol),EDCI (2.11g, 11mmol), HOBt (1.49g, 11mmol) was addedStir into 100 mL CH2Cl2 at room temperature for 30 minutes;N-Boc-ethylenediamine (1.76 g, 11 mmol) was dissolved in 20 mL of CH2Cl2.And added dropwise to the above reaction solution, stirring at room temperature, TLC detection,Until the reaction is complete (about 10 hours). Stop the reaction, adjust the pH to acidity with dilute acid, transfer to a separatory funnel, and separate the liquid. The organic layer is H2O (100 mL×2).Saturated brine (100 mL × 1) was washed and dried over anhydrous Na 2 SO 4 .The organic solvent was evaporated under reduced pressure to give a yellow viscous liquid.Add 20mL of CH2Cl2 to dissolve it, and stir it.Add CF3COOH (10 mL), heat to reflux, TLC detection,Until the reaction is complete (about 2 hours). Stop heating, after cooling to room temperature,Slowly add Et3N to adjust the system to weak alkaline. Transfer the reaction solution to the liquid leakageThe bucket was washed successively with water (50 mL×3) and saturated brine (50 mL×1).The organic layer was dried over anhydrous Na 2 SO 4 . Spin dry organic solvent,The crude product was separated by column chromatography (CH2Cl2:CH3OH=20:1).Obtained pure product of compound 2, 6.2 g of white solid, yield 87%
  • 83
  • [ 117241-31-3 ]
  • trans-2,5-bis(4-hydroxyphenyl)-2,5-dimethylpyrrolidine-1-oxy [ No CAS ]
  • C61H96NO7 [ No CAS ]
  • 84
  • [ 117241-31-3 ]
  • trans-2-(4-hydroxyphenyl)-2,5-dimethyl-5-phenylpyrrolidine-1-oxy [ No CAS ]
  • C61H96NO6 [ No CAS ]
  • 85
  • C19H20NO3 [ No CAS ]
  • [ 117241-31-3 ]
  • C62H96NO7 [ No CAS ]
  • 86
  • 3-(4-benzyloxyphenyl)-2,2-dimethyl-1,4-diazaspiro[4.5]dec-3-ene-8-ol 1-oxyl [ No CAS ]
  • [ 117241-31-3 ]
  • (5s,8s)-2-(4-benzyloxyphenyl)-4-oxido-3,3-dimethyl-1,4-diazaspiro[4.5]dec-1-en-8-yl 3,4,5-tris(dodecyloxy)-benzoate [ No CAS ]
  • (5r,8r)-2-(4-benzyloxyphenyl)-4-oxido-3,3-dimethyl-1,4-diazaspiro[4.5]dec-1-en-8-yl 3,4,5-tris(dodecyloxy)-benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 24h;Inert atmosphere; A round-bottom flask was purged with Ar, then charged with 3-(4-benzyloxyphenyl)-2,2-dimethyl-1,4-diazaspiro[4.5]dec-3-ene-8-ol 1-oxyl (11) (378 mg, 1.0 mmol), Ph3P (576 mg, 2.2 mmol),<strong>[117241-31-3]3,4,5-tris(dodecyloxy)benzoic acid</strong> (1.350 g, 2.0 mmol), and THF (10 mL). DEAD (348 mg, 2.0 mmol) was added to the resultant solution followed by stirring at room temperature for 24 h. The mixture was concentrated in vacuum, and the residue was triturated with Et2O and cooled to 0 . The precipitate was filtered off. The solvent was removed, and the residue was subjected to chromatography (preparative TLC) on silica gel (hexane/EtOAc, 5:1), with collection of the fractions with Rf 0.30 (cis isomer) and Rf 0.35 (trans isomer). The total yield was 58%.
  • 87
  • 2,2-dimethyl-3-(4-benzyloxyphenyl)-8-(4-hydroxyphenyl)-1,4-diazaspiro[4,5]deca-3-ene 1-oxyl [ No CAS ]
  • [ 117241-31-3 ]
  • 4-[(5r,8r)-3-(4-benzyloxyphenyl)-2,2-dimethyl-1-oxido-1,4-diazaspiro[4.5]dec-1-en-8-yl]phenyl 3,4,5-tris(dodecyloxy)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 24h;Inert atmosphere; A round-bottom flask was filled with argon, then charged with compound 8 (455 mg,1 mmol), Ph3P (576 mg, 2.2 mmol), <strong>[117241-31-3]3,4,5-tris(dodecyloxy)benzoic acid</strong> (1.350 g, 2.0 mmol), and dry THF (10mL). Diethyl azodicarboxylate (DEAD) (348 mg, 2.0 mmol) was added to the resulting solution followed bystirring at room temperature for 24 h. The mixture was concentrated in vacuum, the residue was trituratedwith Et2O, cooled to 0 , and the precipitate was filtered off. Evaporation of the solvent gave a solid, whichwas purified by preparative TLC on silica gel with hexane/EtOAc (80:20) to give the title compound 10 as a paleyellow solid (911 mg, 82%), which was used for the next step without further purification. An analytical samplewas prepared by recrystallization from EtOH to obtain ester 10 as a pale yellow amorphous solid mp 38-40 C(EtOH). IR (solid, KBr, νmax, cm1): 1747 (C=O), 1587 (C=N). ESR: t, AN 1.45 mT, giso 2.0058. Anal. calcd forC72H107N2O7 (1112.63): , 77.72; H, 9.69; N, 2.52. Found: , 77.42; H, 9.63; N, 2.50%
  • 88
  • [ 1517-05-1 ]
  • [ 117241-31-3 ]
  • 2-azidoethyl 3,4,5-tris(dodecyloxy)benzoate [ No CAS ]
  • 89
  • [ 107386-97-0 ]
  • [ 117241-31-3 ]
  • thiophene-2,3,4,5-tetrayltetrakis(benzene-4,1-diyl) tetrakis(3,4,5-tris(dodecyloxy)benzoate) [ No CAS ]
  • 90
  • 4,7-bis(4-(tert-butyl)phenyl)benzo[c][1,2,5]thiadiazol-5-amine [ No CAS ]
  • [ 117241-31-3 ]
  • N-(4,7-bis(4-(tert-butyl)phenyl)benzo[c][1,2,5]thiadiazol-5-yl)-3,4,5-tris(dodecyloxy)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With oxalyl dichloride; hexanenitrile; Triphenylphosphine oxide; for 0.5h; Add in a 50mL two-port bottleTriphenylphosphine oxide (257 mg, 0.925 mmol) and nitrile,Oxalyl chloride (117 mg, 1.2 mmol) was added dropwise to the heterogeneous mixture.After the reaction liquid is clear and transparent, it is stirred at room temperature for 10 min;Add 3,4,5-tridodecyloxybenzoic acid (624 mg, 0.925 mmol),Subsequently, a solution of 4,7-di-4-tert-butylphenyl-2,1,3-benzothiadiazol-5amine (500 mg, 1.2 mmol) in nitrile was added dropwise, and the mixture was stirred for 30 min.After the reaction was completed, the reaction was diluted with methylene chloride, washed with saturated sodium hydrogen sulfate, and then evaporated and evaporated to remove solvent. The residue was washed with petroleum ether: dichloromethane (V: V = 1:1) After separation by column chromatography, the residue was recrystallized to give 680 mg (yield: 60%).
  • 91
  • 4,7-bis(4-fluorophenyl)benzo[c][1,2,5]thiadiazol-5-amine [ No CAS ]
  • [ 117241-31-3 ]
  • N-(4,7-bis(4-fluorophenyl)benzo[c][1,2,5]thiadiazol-5-yl)-3,4,5-tris(dodecyloxy)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With oxalyl dichloride; hexanenitrile; Triphenylphosphine oxide; for 0.5h; Add triphenylphosphine oxide (190 mg, 0.681 mmol) and nitrile to a 50 mL two-necked flask.Oxalyl chloride (112 mg, 0.885 mmol) was added dropwise to the heterogeneous mixture. After the reaction mixture was clear and transparent, it was stirred at room temperature for 10 min; and 3,4,5-tridodecyloxybenzoic acid (460 mg, 0.681 mmol) was added. ), then drop by dropA solution of 4,7-di-4-fluorophenyl-2,1,3-benzothiadiazol-5amine (300 mg, 0.885 mmol) in nitrile was stirred for 30 min.After the reaction was completed, the reaction mixture was diluted with methylene chloride, washed with saturated sodium hydrogen sulfate, and then evaporated and evaporated to remove solvent. The residue was washed with petroleum ether: dichloromethane (V:V=2:1) After separation by column chromatography, recrystallization was carried out to obtain the target product 115 mg.(Yield: 17%).
  • 92
  • 4,7-diphenylbenzo[c][1,2,5]thiadiazol-5-amine [ No CAS ]
  • [ 117241-31-3 ]
  • N-(4,7-diphenylbenzo[c][1,2,5]thiadiazol-5-yl)-3,4,5-tris(dodecyloxy)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With oxalyl dichloride; hexanenitrile; Triphenylphosphine oxide; for 0.5h; Triphenylphosphine oxide (423 mg, 1.524 mmol) and nitrile were added to a 50 mL two-necked flask, and oxalyl chloride (252 mg, 1.89 mmol) was added dropwise to the heterogeneous mixture. After the reaction solution was clear and transparent, it was stirred at room temperature. 10 min; 3,4,5-tridodecyloxybenzoic acid (1.03 g, 1.524 mmol) was added, followed by dropwise additionA solution of 4,7-diphenyl-2,1,3-benzothiadiazol-5amine (600 mg, 1.89 mmol) in nitrile was stirred for 30 min. After the reaction was completed, the reaction mixture was diluted with methylene chloride, washed with saturated sodium hydrogen sulfate, and then evaporated and evaporated to remove solvent. The residue was washed with petroleum ether: dichloromethane (V:V=2:1) After separation by column chromatography, the residue was recrystallized to give 135 mg (yield: 9%).
  • 93
  • 4,7-bis(4-(9H-carbazol-9-yl)phenyl)benzo[c][1,2,5]thiadiazol-5-amine [ No CAS ]
  • [ 117241-31-3 ]
  • N-(4,7-bis(4-(9H-carbazol-9-yl)phenyl)benzo[c][1,2,5]thiadiazol-5-yl)-3,4,5-tris(dodecyloxy)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% With oxalyl dichloride; hexanenitrile; Triphenylphosphine oxide; for 0.5h; Triphenylphosphine oxide (230 mg, 0.826 mmol) and nitrile were added to a 50 mL two-necked vial, and oxalyl chloride (104 mg, 1.07 mmol) was added dropwise to the heterogeneous mixture until the reaction was clear and transparent at room temperature. Stir for 10min;Add 3,4,5-tridodecyloxybenzoic acid (558 mg, 0.826 mmol), followed by dropwise addition of 4,7-diphenyloxazole-2,1,3-benzothiadiazol-5amine (680 mg, 1.07 mmol) in nitrile solution, the reaction was stirred for 30 min. After the reaction was completed, the reaction mixture was diluted with methylene chloride, washed with saturated sodium hydrogen sulfate, and then evaporated and evaporated to remove solvent. The residue was washed with petroleum ether: methylene chloride (V:V = 1:1.3). After separation by column chromatography, the residue was recrystallized to give 280 mg (yield: 26%).
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