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[ CAS No. 7778-83-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 7778-83-8
Chemical Structure| 7778-83-8
Chemical Structure| 7778-83-8
Structure of 7778-83-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 7778-83-8 ]

CAS No. :7778-83-8 MDL No. :MFCD00051556
Formula : C12H14O2 Boiling Point : -
Linear Structure Formula :- InChI Key :OLLPXZHNCXACMM-CMDGGOBGSA-N
M.W : 190.24 Pubchem ID :5270647
Synonyms :

Calculated chemistry of [ 7778-83-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.05
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.81
Log Po/w (XLOGP3) : 3.52
Log Po/w (WLOGP) : 2.54
Log Po/w (MLOGP) : 2.77
Log Po/w (SILICOS-IT) : 2.94
Consensus Log Po/w : 2.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.22
Solubility : 0.114 mg/ml ; 0.000597 mol/l
Class : Soluble
Log S (Ali) : -3.76
Solubility : 0.0333 mg/ml ; 0.000175 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.38
Solubility : 0.0802 mg/ml ; 0.000422 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.23

Safety of [ 7778-83-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P273-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319-H413 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7778-83-8 ]

* 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 [ 7778-83-8 ]

[ 7778-83-8 ] Synthesis Path-Downstream   1~24

  • 1
  • [ 7778-83-8 ]
  • 2,3-dibromo-3-phenyl-propionic acid propyl ester [ No CAS ]
  • 3
  • [ 71-23-8 ]
  • cinnamic acid p-tosylhydrazide [ No CAS ]
  • [ 13326-06-2 ]
  • [ 7778-83-8 ]
  • [ 114376-01-1 ]
  • 6
  • [ 67-56-1 ]
  • [ 7778-83-8 ]
  • [ 103-26-4 ]
  • 7
  • [ 71-23-8 ]
  • [ 103-26-4 ]
  • [ 7778-83-8 ]
  • 8
  • [ 103-26-4 ]
  • [ 71-36-3 ]
  • [ 7778-83-8 ]
  • 9
  • [ 7778-83-8 ]
  • [ 52392-64-0 ]
  • 10
  • [ 56289-55-5 ]
  • [ 7778-83-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium 10% on activated carbon; In bmim NTf2;Reactivity (does not react); The hydrogenation of allyl cinnamate can lead to the reduction either of the olefinic bonds, or even hydrogenolysis of the allyl functionality may be observed (Figure 8).Using both ILs, although no hydrogenolysis was observed in either the corresponding Bmim ILs nor the common organic solvent, ethyl acetate, 84 % selectivity was reached using IL (KG51) (Table 18).Table 18
With hydrogen;palladium 10% on activated carbon; In Bmim OctOSO3;Reactivity (does not react); The hydrogenation of allyl cinnamate can lead to the reduction either of the olefinic bonds, or even hydrogenolysis of the allyl functionality may be observed (Figure 8).Using both ILs, although no hydrogenolysis was observed in either the corresponding Bmim ILs nor the common organic solvent, ethyl acetate, 84 % selectivity was reached using IL (KG51) (Table 18).Table 18
With hydrogen;palladium 10% on activated carbon; In 3-methyl-1-(2-(n-propoxy)ethoxycarbonylmethyl)imidazolium octylsulfate;Product distribution / selectivity; The hydrogenation of allyl cinnamate can lead to the reduction either of the olefinic bonds, or even hydrogenolysis of the allyl functionality may be observed (Figure 8).Using both ILs, although no hydrogenolysis was observed in either the corresponding Bmim ILs nor the common organic solvent, ethyl acetate, 84 % selectivity was reached using IL (KG51) (Table 18).Table 18
With hydrogen;palladium 10% on activated carbon; In 3-methyl-1-(propoxyethoxycarbonylmethyl)imidazolium trifluoromethanesulfonimide;Product distribution / selectivity; The hydrogenation of allyl cinnamate can lead to the reduction either of the olefinic bonds, or even hydrogenolysis of the allyl functionality may be observed (Figure 8).Using both ILs, although no hydrogenolysis was observed in either the corresponding Bmim ILs nor the common organic solvent, ethyl acetate, 84 % selectivity was reached using IL (KG51) (Table 18).Table 18
With hydrogen;palladium 10% on activated carbon; In ethyl acetate;Reactivity (does not react); The hydrogenation of allyl cinnamate can lead to the reduction either of the olefinic bonds, or even hydrogenolysis of the allyl functionality may be observed (Figure 8).Using both ILs, although no hydrogenolysis was observed in either the corresponding Bmim ILs nor the common organic solvent, ethyl acetate, 84 % selectivity was reached using IL (KG51) (Table 18).Table 18

  • 11
  • [ 56289-55-5 ]
  • [ 13326-06-2 ]
  • [ 7778-83-8 ]
  • 12
  • [ 71-23-8 ]
  • [ 73789-34-1 ]
  • [ 7778-83-8 ]
  • 13
  • [ 292638-84-7 ]
  • [ 71-23-8 ]
  • [ 201230-82-2 ]
  • [ 15895-95-1 ]
  • [ 7778-83-8 ]
  • 14
  • [ 7778-83-8 ]
  • n-propyl thionocinnamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With tetraphosphorus decasulfide; In 1,4-dioxane;Reflux; General procedure: The thionocinnamates 54refPreviewPlaceHolder1-61 were prepared by the sulfonation of their corresponding oxygenated cinnamates 13 and 47-53, refPreviewPlaceHolder[10] and refPreviewPlaceHolder[34] which in turn were prepared from the corresponding commercially available cinnamic acids and alcohols using P2S5 with little modification (refPreviewPlaceHolderScheme 5) to the literature reported procedure refPreviewPlaceHolder[35]. All the eight cinnamates (13 and 47-53) were freshly recrystallized prior to their use, and the solvent dioxane was freshly dried and distilled. A mixture of the oxygenated cinnamate 13/47-53 (100 mg) and P2S5 (1.5 equivalent) was refluxed in anhydrous dioxane (10 mL), the progress of the reaction was monitored by TLC. After completion of the reaction, the crude reaction mixture was poured into ice-cold water and extracted with ethyl acetate (3 × 30 mL). The combined organic layer was dried over sodium sulfate and evaporated in vacuo, and the residual oil was chromatographed on a silica gel column using petroleum ether. All the novel thionocinnamate 54-61 were fully and unambiguously identified on the basis of their spectral (IR, 1H NMR, 13C NMR spectra and HRMS) analysis.
  • 15
  • [ 71-23-8 ]
  • [ 104-55-2 ]
  • [ 7778-83-8 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide; at 60℃; for 3.0h; General procedure: The catalytic reactions were performed in a round-bottomed flask equipped with a magnetic stirring bar and a reflux condenser. The oxidative esterification was carried out as follows: catalyst (20 mg), aldehyde (1 mmol) and alcohol (5 mmol) were magnetically stirred in the reaction flask at 60 C. H2O2 (2 mmol) was progressively added to the reaction mixture using a syringe. The reactions were stopped after 3 h and the excess hydrogen peroxide was deactivated by the addition of aq. sodium bisulfite. The catalyst was separated from the reaction mixture by filtration. As a two-layer mixture was obtained (organic phase/water phase) after the reaction, the organic products were separated from the aqueous phase by ethyl acetate extractions. The combined organic layers were washed with brine and dried over anhydrous Na2SO4, and then analyzed by GC-MS.
  • 16
  • [ 591-50-4 ]
  • [ 925-60-0 ]
  • [ 7778-83-8 ]
YieldReaction ConditionsOperation in experiment
64%Chromat. With (tetra-n-butylammonium)2[Pd(N-4-methylphenyloxamate)2]*2H2O*MeCN; triethylamine; at 120℃; for 0.5h;Ionic liquid;Catalytic behavior; General procedure: A test-tube with screw cap and valve was charged with a magnetic stir bar, the pre-catalyst 1mol % Pd, the aryl halide (0.50mmol), NEt3 (1.00mmol), the olefin (0.75mmol) and 2-3g of the ionic liquid. The reaction was heated under continuous stirring during 30min at 120C for n-Bu4NBr and in the temperature range 80-120C for the other ionic liquids, namely n-Bu4NCl, BMIMBr and BIMIMPF6. The reaction was monitored using thin liquid chromatography on silica gel. Workup was identical to that described above for the Suzuki reaction.
  • 17
  • [ 7778-83-8 ]
  • [ 1621106-08-8 ]
  • 18
  • [ 7778-83-8 ]
  • [ 1621105-94-9 ]
YieldReaction ConditionsOperation in experiment
With sodium azide; ammonium cerium (IV) nitrate; In acetonitrile; at 0℃;Inert atmosphere; General procedure: To a deoxygenated solution of ethyl cinnamate (176 mg, 1 mmol)and NaN3 (98 mg, 1.5 mmol) in anhydrous MeCN, a deoxygenatedsolution of CAN (1.370 g, 2.5 mmol) in the same solvent (10 mL)was added dropwise at 0 C and stirred well. H2O (400 mL) wasadded to the reaction mixture and the aqueous layer was extractedwith CH2Cl2 (4 × 150 mL). The combined organic extracts werewashed with H2O (2 × 100 mL), and dried over anhydrous Na2SO4.The crude residue, on treatment with anhydrous NaOAc (123 mg,1.5 mmol) in anhydrous acetone (5 mL), followed by usual workupand purification by silica gel column chromatography using petroleumether-EtOAc (98:2) as eluent, afforded 2a as a pale yellowviscous liquid.
  • 19
  • [ 71-23-8 ]
  • [ 300-57-2 ]
  • [ 7778-83-8 ]
  • 20
  • [ 109-99-9 ]
  • [ 35193-63-6 ]
  • [ 7778-83-8 ]
  • C36H34BrO7P [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.7% With N-Bromosuccinimide; at 20℃; for 30h;Inert atmosphere; The substrate is used cinnamic acidPropyl ester (47.6mg, 0.2mmol) and (S) -1,1'- binaphthyl-2,2'-diyl hydrogen phosphate (73.1mg, 0.21mmol, 1.01Equiv.), Was addedAfter N- bromosuccinimide, 30h is reacted, and other experimental conditions were the same method as in Example 1, to obtain a colorless oily liquid 97.2mg, yield 70.7percent.Two non enantiomers by high performance liquid chromatography )The chalcone (41.6mg, 0.2mmol) and (R / S) -1,1'- binaphthyl-2,2'-diyl hydrogen phosphate (73.1mg, 0.21mmol, 1.01Equiv.) Was dissolved in 2mL<strong>[109-99-9]THF</strong> ; and at room temperature, under argon atmosphere, was slowly every 2hWas added N- bromosuccinimide (0.1mmol, 0.5Equiv.) For a total of 4 times was added, N- bromosuccinimide was added, reaction was continued for 24h, the solvent was removed under reduced pressure, the residue by column chromatography gel (ethyl acetate: n-hexane; (1: 10, V / V, 100mL), (1: 5, V / V100mL), (1: 3, V / V, 200mL)), to give a colorless oily liquid121.7mg, yield 86percent.The product form two diastereomers by high performance liquid.
  • 21
  • [ 621-82-9 ]
  • [ 7778-83-8 ]
  • 22
  • [ 71-23-8 ]
  • [ 102-92-1 ]
  • [ 7778-83-8 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 0℃; for 1.0h; General procedure: Compounds A11-A15, A17, A18, A20-A22, B1-B12, C7-C10 and C13-C20 were preparedaccording to method B in Fig 1 by reaction of the corresponding acyl chloride and thecorresponding alcohol. The general procedure was as follows. The mixture of cinnamic acid orcinnamic acids with substituents on the phenyl ring (0.10 mol) and 30 mL thionyl chloridewas refluxed at 75C for 2 h. The excess thionyl chloride was removed under reduced pressure.After the residue was dissolved in 10 mL DCM, the corresponding alcohol (10 mmol) wasadded at 0C. The solution was stirred at 0C for 1 h, and then washed with water (3 × 30 mL)followed by 5% Na2CO3 aqueous solution, and dried over anhydrous sodium sulfate. After filtration,the solvent was removed under reduced pressure. The residue was purified by silica gelcolumn chromatography ( 40 mm × L 40 cm) to afford the desired product.
  • 23
  • [ 109-60-4 ]
  • [ 100-52-7 ]
  • [ 7778-83-8 ]
  • 24
  • [ 540-54-5 ]
  • [ 621-82-9 ]
  • [ 7778-83-8 ]
YieldReaction ConditionsOperation in experiment
88% With 1,1'-(hexane-1,6-diyl)bis(1,8-diazabicyclo[5.4.0]undec-7-enium) dichlorine; In ethanol; water; at 70℃; for 2.2h;Green chemistry; General procedure: Carboxylic acids (1.00 mmol), primary chloroalkanes(1.20mmol) and IL-1 (0.30mmol) were added respectivelyinto a two necked flask equipped with 6mL 50%aqueous ethanol solution under stirring, then raised the systemtemperature to 70C for a needed time in water bath.The progress of the reaction was monitored using thin layer chromatography (TLC). When the reaction was over, thereactor was cooled down to room temperature. The mixturewas diluted with water (10mL) and extracted with ethylacetate (3 × 5mL), the extract was dried over anhydrousNa2SO4,filtered, and concentrated in a rotary evaporatorto collect target product. Meanwhile, the reborn catalystcould be applied in the next cycle was after removing thesolvent and dried at 80C under vacuum for 6h. All theesterification products were further purified by column
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