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[ CAS No. 88038-94-2 ] {[proInfo.proName]}

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Chemical Structure| 88038-94-2
Chemical Structure| 88038-94-2
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Product Details of [ 88038-94-2 ]

CAS No. :88038-94-2 MDL No. :MFCD00017335
Formula : C16H16O2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :HCPBURTZSXRGBN-UHFFFAOYSA-N
M.W : 240.30 Pubchem ID :522891
Synonyms :

Safety of [ 88038-94-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 88038-94-2 ]

* 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 [ 88038-94-2 ]

[ 88038-94-2 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 106-44-5 ]
  • [ 88038-94-2 ]
  • 4-(4-n-propylphenyl)-benzoic acid 4'-methylphenyl ester [ No CAS ]
  • 2
  • [ 18979-50-5 ]
  • [ 88038-94-2 ]
  • 4-(4-n-propylphenyl)-benzoic acid 4'-n-propyloxyphenyl ester [ No CAS ]
  • 3
  • [ 13037-86-0 ]
  • [ 88038-94-2 ]
  • 4-(4-n-propylphenyl)-benzoic acid 4'-n-heptyloxyphenyl ester [ No CAS ]
  • 6
  • [ 122-94-1 ]
  • [ 88038-94-2 ]
  • 4-(4-n-propylphenyl)-benzoic acid 4'-n-butyloxyphenyl ester [ No CAS ]
  • 7
  • [ 2446-69-7 ]
  • [ 88038-94-2 ]
  • 4-(4-n-propylphenyl)-benzoic acid 4'-n-hexylphenyl ester [ No CAS ]
  • 8
  • [ 18979-53-8 ]
  • [ 88038-94-2 ]
  • 4-(4-n-propylphenyl)-benzoic acid 4'-n-pentyloxyphenyl ester [ No CAS ]
  • 10
  • [ 88038-94-2 ]
  • [ 93972-05-5 ]
  • 11
  • [ 88038-94-2 ]
  • [ 65195-14-4 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; [0182] Examples 20-58:; [0183] Step 1 : General Procedure for the Preparation of Acid Chlorides. A solution of acid and oxalyl chloride (1.5 equivalents) in methylene chloride containing a catalytic amount of DMF was stirred under nitrogen at room temperature overnight. The solvent was removed under reduced pressure and the crude acid chloride used in subsequent reactions without purification.
With thionyl chloride; In tetrachloromethane; dichloromethane; Reference Example 54 4-[4-Propylphenyl]benzoyl Chloride A mixture of 2.0 g of 4-(4-propylphenyl]benzoic acid and 30 ml of thionyl chloride is stirred at reflux for 45 minutes. The reaction mixture is evaporated in vacuo to a residue which is evaporated from carbon tetrachloride (2*50 ml) to give a residue which is dissolved in methylene chloride.
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; toluene; at 0℃; for 3.0h; Method FF: To a stirred solution or suspension of the acid (1 mmol, 1 eq) in DCM (3-5 mL) was added few drops of DMF. The resulting solution was cooled to 0 C. in ice bath followed by addition of 2M (COCl)2 in toluene (1 mL, 2 eq.). This mixture was stirred at 0 C. for 3 h, and solvents were removed under vacuum to yield relatively pure acid chloride. The residue was suspended in anhydrous THF (2-3 mL), and resulting suspension was cooled to 0 C. To this suspension was added amino acid (0.5 mmol) dissolved in 1N NaOH solution (1-2 mL). The resulting mixture was stirred at rt for 16 h followed by addition of 1N HCl to pH 3. The resulting mixture was extracted with EtOAc (3×10 mL). The combined organic phase was washed with saturated aq. NaHCO3, brine, and dried over Na2SO4. Solvent was removed under vacuum to yield a mixture of the product along with starting acid as indicated by TLC and mass spectrometry (MS) analysis.The above mixture was dissolved in MeOH (3-5 mL) followed by cooling to 0 C. To this mixture was added 2M solution of TMSCHN2 in diethyl ether (4 ml, 8 eq.). This mixture was stirred at 0 C. for 10 min, and then for 20 min at rt. The yellow solution was concentrated under reduced pressure and purified by column chromatography to yield pure methyl ester.Step 1: DL-3,3,3-Trifluoro-2-[(4'-propyl-biphenyl-4-carbonyl)-amino]-propionic acid methyl ester is prepared from 3,3,3-trifluoro-D,L-alanine and <strong>[88038-94-2]4-(4-n-propylphenyl)benzoic acid</strong> following Method FF (yield=86%). 1H NMR (300 MHz, CDCl3): 7.09-7.86 (m, 2H), 7.69-7.63 (m, 2H), 7.53-7.51 (m, 2H), 7.28-7.25 (m, 2H), 6.87 (d, J=9.00 Hz, 1H), 5.62-5.56 (m, 1H), 3.89 (s, 3H), 2.62 (t, J=6.00 Hz, 2H), 1.72-1.60 (m, 2H), 0.95 (t, J=9.00 Hz, 3H). 19F NMR (282 MHz, CDCl3); -70.87, -73.80.
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 1.0h; Method EE: 4-(4-n-Propylphenyl)benzoic acid (130 mg, 0.53 mmol), DCM (8 ml), DMF (1 drop), and oxalyl chloride (0.09 ml, 1.03 mmol) are combined and stirred at rt for 1 h. The reaction mixture is concentrated in vacuo, and the residue is redissolved in DCM (8 mL). The amine (0.47 mmol) is dissolved in pyridine and combined with the DCM mixture. The combined mixture is stirred at rt for 18 h, and diluted with ethyl acetate. The ethyl acetate solution is washed with water, dried over sodium sulfate, and concentrated in vacuo. The compound was used in the next reaction without further purification.Step 8: (2S,4R)-4-Hydroxy-4-(methoxymethyl)-1-(4'-propylbiphenylcarbonyl)-N-(tetrahydro-2H-pyran-2-yloxy)pyrrolidine-2-carboxamide from 4-(4-propylphenyl) benzoic acid is prepared from (2S,4R)-4-hydroxy-4-(methoxymethyl)-N-(tetrahydro-2H-pyran-2-yloxy)pyrrolidine-2-carboxamide and 4-(4-propylphenyl)benzoic acid following Method EE (yield=85%). ESI(-) calcd. for C28H35N2O6 (495.25), found 495.2.
With oxalyl dichloride;N,N-dimethyl-formamide; In chloroform; at 5 - 40℃; for 2.55h;Inert atmosphere; Into a 250 mL three neck round bottom flask was placed a magnetic stir bar, 3.60 grams (15 mmol) of 4-(-n-propylphenyl)benzoic acid (CAS RN 88038-94-2, TCI America Chemicals Inc.) and 50 mL of chloroform (CAS 865-49-6, Sigma-Aldrich Chem. Co.). To the magnetically stirred slurry was added 5 drops of dimethylformamide (CAS 68-12-2, Alfa-Aesar Chemical Co.) and the reaction was placed under a nitrogen atmosphere then placed in an ice water bath and chilled to 5-10 C. To the stirred heterogeneous mixture was added 3.81 grams (30 mmol) of oxalyl chloride (CAS 79-37-8, Alfa-Aesar Chem. Co.) dropwise from a capillary pipet over approximately 3 minutes. The reaction was then removed from the ice bath and stirred at room temperature for 2 hours. The resulting homogeneous light yellow solution was placed in a pre-heated 40 C. oil bath and warmed with stirring at 40 C. for 30 minutes. The product mixture was removed from the oil bath, filtered through fine filter paper using a Buchner funnel to remove particulates, then the light yellow solution was concentrated to dryness in vacuo. To the flask was added 50 mL chloroform and concentrated to dryness a second time to remove residual oxalyl chloride. The product mixture afforded a light yellow thick liquid which crystallized on cooling to room temperature. The collected weight was 4.16 grams which was used without further purification.
With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 20℃; General procedure: was prepared by stirring amixture of 1a (1.16 g, 5 mmol),SOCl2 (0.59 g, 5 mmol), and several drops of DMF in toluene (30 mL) at ambient temperaturefor 5 hr. The solvent was removed under vacuum. A brown liquid (2a) was obtainedand used to next step without further purifying.
With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 20℃; for 5.0h; General procedure: 2a was prepared by heating and stirring a mixture of 4-ethyl(4-trans-cyclohexyl)benzoicacid(1a) (1.16 g, 5 mmol) and SOCl2 (0.60 g, 5 mmol) and several drops of DMF in toluene (25 mL) at ambient temperature for 5 hr. The solvent was then removed under vaccum condition. A brown liquid (2a) was obtained and used to next step without further purifying.

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