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Product Details of [ 48145-04-6 ]

CAS No. :48145-04-6 MDL No. :MFCD00053696
Formula : C11H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :RZVINYQDSSQUKO-UHFFFAOYSA-N
M.W : 192.21 Pubchem ID :39485
Synonyms :

Calculated chemistry of [ 48145-04-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.18
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.97
TPSA : 35.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.6
Log Po/w (XLOGP3) : 2.37
Log Po/w (WLOGP) : 1.79
Log Po/w (MLOGP) : 1.88
Log Po/w (SILICOS-IT) : 2.29
Consensus Log Po/w : 2.18

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.45
Solubility : 0.688 mg/ml ; 0.00358 mol/l
Class : Soluble
Log S (Ali) : -2.76
Solubility : 0.337 mg/ml ; 0.00175 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.08
Solubility : 0.158 mg/ml ; 0.000822 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.98

Safety of [ 48145-04-6 ]

Signal Word:Danger Class:9
Precautionary Statements:P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330 UN#:3082
Hazard Statements:H302-H319-H372-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 48145-04-6 ]

* 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.

  • Downstream synthetic route of [ 48145-04-6 ]

[ 48145-04-6 ] Synthesis Path-Downstream   1~57

  • 1
  • [ 122-99-6 ]
  • [ 292638-85-8 ]
  • [ 48145-04-6 ]
YieldReaction ConditionsOperation in experiment
99% With dmap; oxo[hexa(trifluoroacetato)]tetrazinc In neat (no solvent) at 80℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction;
With toluene-4-sulfonic acid; hydroquinone Entfernen des entstehenden Methanols;
With sulfuric acid; hydroquinone Entfernen des entstehenden Methanols;
  • 2
  • [ 122-99-6 ]
  • [ 140-88-5 ]
  • [ 48145-04-6 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; hydroquinone Entfernen des entstehenden Aethanols;
With toluene-4-sulfonic acid; hydroquinone Entfernen des entstehenden Aethanols;
  • 4
  • [ 4486-44-6 ]
  • [ 48145-04-6 ]
  • 3-(diisopropoxy-phosphorylsulfanyl)-propionic acid 2-phenoxy-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With 4-methoxy-phenol at 90℃; for 1h;
  • 5
  • [ 48145-04-6 ]
  • [ 2465-65-8 ]
  • 3-(diethoxy-phosphorylsulfanyl)-propionic acid 2-phenoxy-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With 4-methoxy-phenol at 90℃; for 1h;
  • 6
  • [ 33707-36-7 ]
  • [ 48145-04-6 ]
  • 2-methyl 6-(2-phenoxyethyl) (1RS,4RS,6RS)-2-azabicyclo[2.2.2]oct-7-ene-2,6-dicarboxylate [ No CAS ]
  • 2-methyl 6-(2-phenoxyethyl) (1RS,4RS,6SR)-2-azabicyclo[2.2.2]oct-7-ene-2,6-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 22% 2: 12% at 160℃; for 15h;
  • 7
  • [ 591-50-4 ]
  • [ 48145-04-6 ]
  • [ 90094-75-0 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine In toluene at 100℃; for 20h;
  • 8
  • [ 48145-04-6 ]
  • polymer; monomer(s): acrylic acid 2-phenoxy-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (2-hydroxycyclohexyl)(phenyl)methanone at 25℃; UV-irradiation;
  • 9
  • 2,4-dihydroxy-5-(4-(2-(N-(2-methacryloyloxyethyl)carbamoyloxy)ethyl)phenylazo)benzophenone [ No CAS ]
  • [ 48145-04-6 ]
  • [ 140-88-5 ]
  • None [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis-(2,4-dimethylvaleronitrile) at 80℃; for 0.666667h; 3 0.03 part by weight of BMAC synthesized in Example 1, 100 parts by weight of phenoxyethyl acrylate, 15 parts by weight of ethyl acrylate and 0.5 part by weight of 2,2'-azobis (2,4-dimethyl valeronitrile) were blended homogeneously, and the resultant was poured into a lens mold. Then the blended solution was polymerized at 80°C for 40 minutes to form a lens. The resulting lens was used as a sample for measuring light transmittance of a ray having a wave length of 220 to 800 nm (Figure 2). Further, after the lens was subjected to elusion treatment by immersing in ethanol at 40°C for 24 hours, the light transmittance was measured again, whereupon no change in the spectrum before and after the elution treatment. This shows that the polymerizable dye was chemically bonded in the material.
  • 10
  • [ 48145-04-6 ]
  • [ 15625-89-5 ]
  • poly(2-phenoxyethyl acrylate)-net-poly(trimethylolpropane triacrylate), photocured stereolithography; monomer(s): 2-phenoxyethyl acrylate; trimethylolpropane triacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Camphorquinone UV-irradiation;
  • 11
  • [ 217825-79-1 ]
  • [ 48145-04-6 ]
  • poly(phenoxyethyl acrylate-co-tribromophloroglucinol triacrylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2-diethoxyacetophenone
  • 12
  • [ 48145-04-6 ]
  • poly(phenoxyethyl acrylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2-diethoxyacetophenone
  • 13
  • [ 217825-08-6 ]
  • [ 48145-04-6 ]
  • poly(1,2-bis(acryloyloxy)tetrabromobenzene-co-phenoxyethyl acrylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2-diethoxyacetophenone
YieldReaction ConditionsOperation in experiment
With 4-cyanobenzenesulfinic acid, tetrabutylammonium salt; triphenylsulfonium hexafluoroantimonate Actinic radiation; 1 Two separate mixtures of SR339, each with 1 weight percent each of triarylsulfonium hexafluoroantimonate and the substituted tetrabutylammonium benzenesulfinate of Preparative Examples 6 or 7, were prepared. For Example 1, 1.1 weight percent of tetrabutylammonium 4-cyanobenzenesulfinate was used, whereas for Example 2, 1.0 weight percent of tetrabutylammonium 4-ethoxycarbonylbenzenesulfinate was used. Each sample was evaluated for rate and extent of cure by photo differential scanning calorimetry (photo-DSC) using a model DSC2920 calorimeter (availabe from TA Instruments, New Castle, DE) with light from a 100W medium pressure mercury that was filtered through a Model GG400 long pass filter (available from Esco Products, Oak Ridge, NJ). The results are given in Table 3. Table 3: Curing of Examples 1-2 Example Substituted tetrabutylammonium benzensulfinate Initial slope (W/g-min) Time to peak maximum (min) Total heat (J/g) 1 4-cyano 32.8 0.41 363.6 2 4-ethoxycarbonyl 21.3 0.47 314.7
with filter (GG400); 7 Two separate mixtures of SR339, each with 1 weight percent each of triarylsulfonium 4-cyanobenzenesulfinate, were prepared. Each sample was evaluated for rate and extent of cure by photo differential scanning calorimetry (photo-DSC) using a model DSC2920 calorimeter (available from TA Instruments, New Castle, DE) with light from a 100W medium pressure mercury that was either unfiltered or was filtered through a Model GG400 long pass filter (available from Esco Products, Oak Ridge, NJ) according to the data in Table 3. The results are given in Table 3. Table 3: Curing of Examples 6-7 Example Filter Initial Slope (W/g-min) Time to peak maximum (min) Total evolved heat (J/g) 6 None 209.5 0.13 359.8 7 GG400 33.2 0.33 335.3
without filter; 6 Two separate mixtures of SR339, each with 1 weight percent each of triarylsulfonium 4-cyanobenzenesulfinate, were prepared. Each sample was evaluated for rate and extent of cure by photo differential scanning calorimetry (photo-DSC) using a model DSC2920 calorimeter (available from TA Instruments, New Castle, DE) with light from a 100W medium pressure mercury that was either unfiltered or was filtered through a Model GG400 long pass filter (available from Esco Products, Oak Ridge, NJ) according to the data in Table 3. The results are given in Table 3. Table 3: Curing of Examples 6-7 Example Filter Initial Slope (W/g-min) Time to peak maximum (min) Total evolved heat (J/g) 6 None 209.5 0.13 359.8 7 GG400 33.2 0.33 335.3
With 1,2-propylene cyclic carbonate; tetrabutylammonium naphthalene-1-sulfinate with filter (GG400); 11 Four separate mixtures of SR339, each with 1 weight percent of propylene carbonate and 1 weight percent each or the naphthalene sulfinates of Preparative Examples 8 or 9, were prepared. For Examples 10 and 11, triphenylsulfonium naphthalene-1-sulfinate was used, whereas for Examples 12 and 13, triphenylsulfonium naphthalene-2-sulfinate was used. Each sample was evaluated for rate and extent of cure by photo differential scanning calorimetry (photo-DSC) using the method of Examples 6-7. The results are given in Table 4. Table 4: Curing of Examples 10-13 Example Tetrabutylammonium Filter Initial Slope (W/g-min) Time to peak maximum (min) Total evolved heat (J/g) 10 Naphthalene-1-sulfinate None 381 0.09 420 11 Naphthalene-1-sulfinate GG400 14.2 0.47 383 12 Naphthalene-2-sulfinate None 242 0.10 388 13 Naphthalene-2-sulfinate GG400 0.15 0.81 277
With 1,2-propylene cyclic carbonate; tetrabutylammonium naphthalene-1-sulfinate without filter; 10 Four separate mixtures of SR339, each with 1 weight percent of propylene carbonate and 1 weight percent each or the naphthalene sulfinates of Preparative Examples 8 or 9, were prepared. For Examples 10 and 11, triphenylsulfonium naphthalene-1-sulfinate was used, whereas for Examples 12 and 13, triphenylsulfonium naphthalene-2-sulfinate was used. Each sample was evaluated for rate and extent of cure by photo differential scanning calorimetry (photo-DSC) using the method of Examples 6-7. The results are given in Table 4. Table 4: Curing of Examples 10-13 Example Tetrabutylammonium Filter Initial Slope (W/g-min) Time to peak maximum (min) Total evolved heat (J/g) 10 Naphthalene-1-sulfinate None 381 0.09 420 11 Naphthalene-1-sulfinate GG400 14.2 0.47 383 12 Naphthalene-2-sulfinate None 242 0.10 388 13 Naphthalene-2-sulfinate GG400 0.15 0.81 277
With 1,2-propylene cyclic carbonate; tetrabutylammonium naphthalene-2-sulfinate with filter (GG400); 13 Four separate mixtures of SR339, each with 1 weight percent of propylene carbonate and 1 weight percent each or the naphthalene sulfinates of Preparative Examples 8 or 9, were prepared. For Examples 10 and 11, triphenylsulfonium naphthalene-1-sulfinate was used, whereas for Examples 12 and 13, triphenylsulfonium naphthalene-2-sulfinate was used. Each sample was evaluated for rate and extent of cure by photo differential scanning calorimetry (photo-DSC) using the method of Examples 6-7. The results are given in Table 4. Table 4: Curing of Examples 10-13 Example Tetrabutylammonium Filter Initial Slope (W/g-min) Time to peak maximum (min) Total evolved heat (J/g) 10 Naphthalene-1-sulfinate None 381 0.09 420 11 Naphthalene-1-sulfinate GG400 14.2 0.47 383 12 Naphthalene-2-sulfinate None 242 0.10 388 13 Naphthalene-2-sulfinate GG400 0.15 0.81 277
With 1,2-propylene cyclic carbonate; tetrabutylammonium naphthalene-2-sulfinate without filter; 12 Four separate mixtures of SR339, each with 1 weight percent of propylene carbonate and 1 weight percent each or the naphthalene sulfinates of Preparative Examples 8 or 9, were prepared. For Examples 10 and 11, triphenylsulfonium naphthalene-1-sulfinate was used, whereas for Examples 12 and 13, triphenylsulfonium naphthalene-2-sulfinate was used. Each sample was evaluated for rate and extent of cure by photo differential scanning calorimetry (photo-DSC) using the method of Examples 6-7. The results are given in Table 4. Table 4: Curing of Examples 10-13 Example Tetrabutylammonium Filter Initial Slope (W/g-min) Time to peak maximum (min) Total evolved heat (J/g) 10 Naphthalene-1-sulfinate None 381 0.09 420 11 Naphthalene-1-sulfinate GG400 14.2 0.47 383 12 Naphthalene-2-sulfinate None 242 0.10 388 13 Naphthalene-2-sulfinate GG400 0.15 0.81 277
With 4-cyanobenzenesulfinic acid, tetrabutylammonium salt Actinic radiation; 2 Two separate mixtures of SR339, each with 1.0 weight percent each of the tetrabutylammonium benzenesulfinate of Preparative Examples 6 or 7, were prepared. Each sample was evaluated for rate and extent of cure by photo differential scanning calorimetry according to the method of Comparative Example 1. The results are given in Table 5. Table 5: Curing of Comparative Examples 2-3 Comparative Example Substituted tetrabutylammonium benzensulfinate Initial slope (W/g-min) Time to peak maximum (min) Total heat (J/g) 2 4-Cyano 0 0 0 3 4-Ethoxycarbonyl 0 0 0
With 4-cyanobenzenesulfinic acid, tetrabutylammonium salt for 0.0125h; Irradiation using 100W quartz-tungsten-halogen (QTH) light source; 3 A mixture of SR339 with 1.0 weight percent of triarylsulfonium hexafluorophosphate and 1.0 weight percent of tetrabutylammonium 4-cyanobenzenesulfinate was prepared in a screw-cap vial. The mixture was purged with nitrogen gas for 45 seconds and then the vial was sealed and the sample was irradiated wtih a 100W quartz-tungsten-halogen (QTH) light source (model I-100, available Cuda Fiberoptics, Jacksonvill, FL) by holding and slowly agitating the vial approximately 2cm in front of the light source. The light source shutter was fully open. Cure time was considered to be the time that it took for the solution viscosity to increase so that the liquid no longer flowed in teh vial as the vial was agitated. The mixture was cured in 5 seconds.
With 4-cyanobenzenesulfinic acid, tetrabutylammonium salt for 0.0125h; Irradiation using Model 5560 dental curing light; 4 A mixture of SR339 with 1.0 weight percent of triarylsulfonium hexafluorophosphate and 1.0 weight percent of tetrabutylammonium 4-cyanobenzenesulfinate was prepared in a screw-cap vial. The mixture was purged with nitrogen gas for 45 seconds and then the vial was sealed and the sample was irradiated wtih a MOdle 5560 dental curing light (obtained from 3M Company, St. Paul, MN) by holding and slowly agitating the vial approximately 2cm in front of the light source. Cure time was considered to be the time that it took for the solution viscosity to increase so that the liquid no longer flowed in teh vial as the vial was agitated. The mixture was cured in 40 seconds.
With 4-carboethoxybenzenesulfinic acid, tetrabutylammonium salt Actinic radiation; 3 Two separate mixtures of SR339, each with 1.0 weight percent each of the tetrabutylammonium benzenesulfinate of Preparative Examples 6 or 7, were prepared. Each sample was evaluated for rate and extent of cure by photo differential scanning calorimetry according to the method of Comparative Example 1. The results are given in Table 5. Table 5: Curing of Comparative Examples 2-3 Comparative Example Substituted tetrabutylammonium benzensulfinate Initial slope (W/g-min) Time to peak maximum (min) Total heat (J/g) 2 4-Cyano 0 0 0 3 4-Ethoxycarbonyl 0 0 0
With 4-carboethoxybenzenesulfinic acid, tetrabutylammonium salt; triphenylsulfonium hexafluoroantimonate Actinic radiation; 2 Two separate mixtures of SR339, each with 1 weight percent each of triarylsulfonium hexafluoroantimonate and the substituted tetrabutylammonium benzenesulfinate of Preparative Examples 6 or 7, were prepared. For Example 1, 1.1 weight percent of tetrabutylammonium 4-cyanobenzenesulfinate was used, whereas for Example 2, 1.0 weight percent of tetrabutylammonium 4-ethoxycarbonylbenzenesulfinate was used. Each sample was evaluated for rate and extent of cure by photo differential scanning calorimetry (photo-DSC) using a model DSC2920 calorimeter (availabe from TA Instruments, New Castle, DE) with light from a 100W medium pressure mercury that was filtered through a Model GG400 long pass filter (available from Esco Products, Oak Ridge, NJ). The results are given in Table 3. Table 3: Curing of Examples 1-2 Example Substituted tetrabutylammonium benzensulfinate Initial slope (W/g-min) Time to peak maximum (min) Total heat (J/g) 1 4-cyano 32.8 0.41 363.6 2 4-ethoxycarbonyl 21.3 0.47 314.7
With triphenylsulfonium hexafluoroantimonate Actinic radiation; 1 A mixture of SR339 and 1 weight percent of Ar3S+SbF6- was prepared. The sample was evaluated for rate and extent of cure by photo differential scanning calorimetry (photo-DSC) using a model DSC2920 calorimeter (availabe from TA Instruments, New Castle, DE) with light from a 100W medium pressure mercury that was filtered through a Model GG400 long pass filter (available from Esco Products, Oak Ridge, NJ). The results are given in Table 4. Table 4: Curing of Comparative Example 1 Comparative Example Initial slope (W/g-min) Time to peak maximum (min) Total evolved heat (J/g) 1 0 0 0
for 0.0125h; Irradiation using 100W quartz-tungsten-halogen (QTH) light source; 4 a mixture of SR339 with 1.0 weight percent of triarylsulfonium hexafluorophosphate was prepared in a screw-cap vial. The mixture was purged with nitrogen gas for 45 seconds and then the vial was sealed and the sample was irradiated as described in Example 3. Cure time was considered to be the time that it took for the solution viscosity to increase so that the liquid no longer flowed in the vial as the vial was agitated. The mixture was cured in 24 seconds.
for 0.0125h; Irradiation with a Model 5560 dental curing light; 5 a mixture of SR339 with 1.0 weight percent of triarylsulfonium hexafluorophosphate was prepared in a screw-cap vial. The mixture was purged with nitrogen gas for 45 seconds and then the vial was sealed and the sample was irradiated as described in Example 4. Cure time was considered to be the time that it took for the solution viscosity to increase so that the liquid no longer flowed in the vial as the vial was agitated. The mixture did not cure. After 40 seconds the mixture still flowed in the vial.

  • 15
  • [ 122-99-6 ]
  • [ 497-19-8 ]
  • [ 814-68-6 ]
  • [ 48145-04-6 ]
YieldReaction ConditionsOperation in experiment
In benzene 2 (Compound No. 23) EXAMPLE 2 β-phenoxyethylacrylate (Compound No. 23) This compound was prepared according to a known process (Chemical Abstracts Vol. 59, 11323a). Namely, acrylic acid-chloride (5g) was added slowly under ice cooling into the mixture of β-phenoxyethylalcohol (6.75g), sodium-carbonate (2.9g), cuprous chloride (0.2g) and benzene (50ml) with stirring. The mixture was allowed to stand 15 hours at room temperature and then refluxed for 4 hours. The reaction mixture was treated according to the above mentioned known process, giving a crude product (6.6g). The crude product on fractionation gave a fraction (4.7g), b.p. 88.0° C./0.1mmHg, of β-phenoxy-ethyl acrylate.
  • 16
  • [ 15214-89-8 ]
  • [ 48145-04-6 ]
  • [ 80-62-6 ]
  • poly(2-acrylamido-2-methylpropanesulfonic acid-co-methyl methacrylate-co-2-phenoxyethyl acrylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile); In N,N-dimethyl-formamide; at 95℃; for 6h; In a synthesis reactor Accelerator SLT100 from Chemspeed, per reaction vessel 0.21 ml of initiator solution 2 was added to 6.72 ml of monomer solution 1. With shaking, the mixture was then heated at 95 C. for 4 h, a further 0.07 ml of initiator solution 2 was then added and the polymerization was concluded at 95 C. over a period of 2 h.; Monomer solution 1: Mixture comprising 150 mg of methyl methacrylate, 450 mg of 2-phenoxyethyl acrylate and 300 mg of <strong>[15214-89-8]2-acrylamido-2-methylpropanesulfonic acid</strong> dissolved in DMF to 8.64 ml. Initiator solution 2: 100 mg of 2,2'-azobis(2-methylpropionitrile) dissolved in DMF to 1.00 ml.
  • 17
  • [ 151285-25-5 ]
  • 2-(2'-hydroxy-5'-(3-(methylacryloxy)propyl)-3-tert-butylphenyl)-5-chloro-2H-benzotriazol [ No CAS ]
  • [ 141-32-2 ]
  • [ 2082-81-7 ]
  • [ 48145-04-6 ]
  • [ 97-88-1 ]
  • poly(1,4-butanediol dimethacrylate-co-3-(2',6'-dichloro-4'-nitrophenylazo)-9-(2'-methacryloyloxyethyl)carbazole-co-ethylene glycol phenyl ether acrylate-co-2-(2'-hydroxy-5'-methacrylyloxypropyl-3'-tert-butylphenyl) - 5-chloro-2H-benzotriazole-co-n-butyl acrylate-co-n-butyl methacrylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile); at 60 - 95℃; for 48h; 0.01% by weight of the colorant thus obtained, 54% by weight of ethylene glycol phenyl ether acrylate, 39.7% by weight of n-butyl methacrylate, 4.0% by weight of n-butyl acrylate, 2.0% by weight of <strong>[2082-81-7]1,4-butanediol dimethacrylate</strong> employed as a crosslinking agent, 0.3% by weight of 2-(2'-hydroxy-5'-methacrylyloxypropyl-3'-tert-butylphenyl) - 5-chloro-2H-benzotriazole employed as an UV absorber and an appropriate amount of 2,2-azobisisobutyronitrile employed as a polymerization initiator were mixed together and the resultant mixture was introduced into a test tube. Then it was polymerized in a thermostat at 60C for 24 ours, in an air oven at 95C for 24 hours and in an vacuum oven at 95C. Thus, a soft base material for intraocular lenses colored in orange was obtained.
  • 18
  • [ 141-32-2 ]
  • [ 2082-81-7 ]
  • [ 48145-04-6 ]
  • [ 97-88-1 ]
  • poly(1,4-butanediol dimethacrylate-co-ethylene glycol phenyl ether acrylate-co-n-butyl acrylate-co-n-butyl methacrylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-(5'-hydroxy-3'-methyl-1'-phenyl-4'-pyrazylylmethylene)-1-(4'-methacryloyloxymethylphenyl)-3-methyl-2-pyrazolin-5-one; 1-[4'-(4'-methacryloyloxyethylphenylazo)phenylazo]-2-naphthol; 2,2'-azobis(isobutyronitrile); at 60 - 95℃; for 48h;Air oven; vacuum oven; 0.006% by weight of the yellow colorant obtained above, 0.0008% by weight of the red colorant, 53.9% by weight of ethylene glycol phenyl ether acrylate, 39.7% by weight of n-butyl methacrylate, 4 . 0% by weight of n-butyl acrylate, 2.0% by weight of <strong>[2082-81-7]1,4-butanediol dimethacrylate</strong> employed as a crosslinking agent, 0.3% by weight of 2-(2'-hydroxy-5'-methacryloxypropyl-3'-tert-butylphenyl)-5 -chloro-2H-benzotriazole employed as an UV light absorber, and a trace amount of 2,2-azobisisobutyronitrile employed as a polymerization initiator were mixed together and supplied into a test tube. Then the mixture was polymerized in a thermostat at 60C for 24 hours, in an air oven at 95C for 24 hours and then in a vacuum oven at 95C to thereby give a soft base material for intraocular lenses (a base material for ocular lenses) in an orange color.
  • 19
  • [ 74-85-1 ]
  • [ 48145-04-6 ]
  • poly(ethylene-co-(2-phenoxyethyl acrylate)) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In para-xylene at 120℃; for 18h; 43 In a nitrogen-filled drybox, a 40 mL glass insert was loaded with the nickel compound and, optionally, a Lewis acid (e.g., BPh3 or B(C6F5)3) and borate (e.g., NaBAF or LiBArF) and any other specified cocatalysts. Next, the solvent was added to the glass insert followed by the addition of any co-solvents and then comonomers. The insert was greased and capped. The glass insert was then loaded in a pressure tube inside the drybox. The pressure tube was then sealed, brought outside of the drybox, connected to the pressure reactor, placed under the desired ethylene pressure and shaken mechanically. After the stated reaction time, the ethylene pressure was released and the glass insert was removed from the pressure tube. The polymer was precipitated by the addition of MeOH (20 mL). The polymer was then collected on a frit and rinsed with MeOH and, optionally, acetone. The polymer was transferred to a pre-weighed vial and dried under vacuum overnight. The polymer yield and characterization were then obtained.
In para-xylene at 120℃; for 18h; 45 In a nitrogen-filled drybox, a 40 mL glass insert was loaded with the nickel compound and, optionally, a Lewis acid (e.g., BPh3 or B(C6F5)3) and borate (e.g., NaBAF or LiBArF) and any other specified cocatalysts. Next, the solvent was added to the glass insert followed by the addition of any co-solvents and then comonomers. The insert was greased and capped. The glass insert was then loaded in a pressure tube inside the drybox. The pressure tube was then sealed, brought outside of the drybox, connected to the pressure reactor, placed under the desired ethylene pressure and shaken mechanically. After the stated reaction time, the ethylene pressure was released and the glass insert was removed from the pressure tube. The polymer was precipitated by the addition of MeOH (20 mL). The polymer was then collected on a frit and rinsed with MeOH and, optionally, acetone. The polymer was transferred to a pre-weighed vial and dried under vacuum overnight. The polymer yield and characterization were then obtained.
In para-xylene at 120℃; for 18h; 44 In a nitrogen-filled drybox, a 40 mL glass insert was loaded with the nickel compound and, optionally, a Lewis acid (e.g., BPh3 or B(C6F5)3) and borate (e.g., NaBAF or LiBArF) and any other specified cocatalysts. Next, the solvent was added to the glass insert followed by the addition of any co-solvents and then comonomers. The insert was greased and capped. The glass insert was then loaded in a pressure tube inside the drybox. The pressure tube was then sealed, brought outside of the drybox, connected to the pressure reactor, placed under the desired ethylene pressure and shaken mechanically. After the stated reaction time, the ethylene pressure was released and the glass insert was removed from the pressure tube. The polymer was precipitated by the addition of MeOH (20 mL). The polymer was then collected on a frit and rinsed with MeOH and, optionally, acetone. The polymer was transferred to a pre-weighed vial and dried under vacuum overnight. The polymer yield and characterization were then obtained.
In para-xylene at 120℃; for 18h; 46 In a nitrogen-filled drybox, a 40 mL glass insert was loaded with the nickel compound and, optionally, a Lewis acid (e.g., BPh3 or B(C6F5)3) and borate (e.g., NaBAF or LiBArF) and any other specified cocatalysts. Next, the solvent was added to the glass insert followed by the addition of any co-solvents and then comonomers. The insert was greased and capped. The glass insert was then loaded in a pressure tube inside the drybox. The pressure tube was then sealed, brought outside of the drybox, connected to the pressure reactor, placed under the desired ethylene pressure and shaken mechanically. After the stated reaction time, the ethylene pressure was released and the glass insert was removed from the pressure tube. The polymer was precipitated by the addition of MeOH (20 mL). The polymer was then collected on a frit and rinsed with MeOH and, optionally, acetone. The polymer was transferred to a pre-weighed vial and dried under vacuum overnight. The polymer yield and characterization were then obtained.

  • 20
  • [ 74-85-1 ]
  • [ 48145-04-6 ]
  • poly(ethylene-co-(2-phenoxyethyl acrylate)) [ No CAS ]
  • poly(2-phenoxyethyl acrylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1,2,4-trichlorobenzene (TCB) at 120℃; for 18h; 14 In a drybox, a glass insert was loaded with the isolated Ni compounds. Solvent and optionally comonomers were added to the glass insert. A Lewis acid cocatalyst [typically BPh3 or B(C6F5)3] was often added to the solution. The insert was then capped and sealed. Outside of the drybox, the tube was placed under ethylene and was shaken mechanically at desired temperature listed in Table 1 for about 18 h. The resulted reaction mixture was blended with methanol, filtered, repeatedly washed with methanol and dried in vacuo.
  • 21
  • [ 74-85-1 ]
  • [ 48145-04-6 ]
  • [ 292638-85-8 ]
  • poly((ethylene-co-(methyl acrylate))-co-((methyl acrylate)-co-(phenoxyethyl acrylate))) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethene; acrylic acid methyl ester With [dodecyl(tetramethyl)cyclopentadienyl]iron carbonyl dimer; 2-butyl iodide In toluene at 150℃; for 0.166667h; Stage #2: 2-phenoxyethyl acrylate In toluene at 20 - 150℃; for 0.5h; 16 A 400 mL stainless-steel autoclave was dried sufficiently, and a gas in the autoclave was displaced with a nitrogen gas. There were put in the autoclave, at ordinary temperature and atmospheric pressure, using a syringe, 18 mL of methyl acrylate manufactured by Tokyo Chemical Industry Co., Ltd., 4 mL of a toluene solution of [dodecyl(tetramethyl)cyclopentadienyl]iron carbonyl dimer (transition metal compound) obtained in Reference Example 2 having a concentration of 0.05 mol/L, and 76 mL of purified toluene as a polymerization solvent. After adding ethylene (olefin) thereto, the mixture was heated up to 150° C., and ethylene (olefin) was pressed at 150° C. into the autoclave up to its pressure of 4.0 MPa, thereby stabilizing the system. Finally, 2.0 mL of a toluene solution of 2-iodobutane (manufactured by Tokyo Chemical Industry Co., Ltd.) having a concentration of 1.0 mol/L was put therein, thereby polymerizing methyl acrylate and ethylene at 150° C. for 10 minutes, this polymerization step being referred to as the first polymerization step. The autoclave was cooled down to 20° C. or lower, and the inner pressure thereof was depressed till atmospheric pressure. There was added 50 mL of phenoxyethyl acrylate to the autoclave, and the mixture was heated again up to 150° C., thereby further polymerizing phenoxyethyl acrylate and the remaining methyl acrylate at 150° C. for 30 minutes, this polymerization step being referred to as the second polymerization step. The polymerization reaction mixture was subjected to distillation under reduced pressure to distil away the remaining monomer (methyl acrylate and phenoxyethyl acrylate) and the solvent (toluene). The resultant solid was dried for three hours in a vacuum dryer (80° C.), thereby obtaining 21 g of a block copolymer consisting of (i) a random copolymer block of methyl acrylate with ethylene, and (ii) a random copolymer block of methyl acrylate with phenoxyethyl acrylate. Said block copolymer had a weight average molecular weight (Mw) of 27,000 and a number average molecular weight (Mn) of 9,500, in terms of a molecular weight of polystyrene. Its molecular weight distribution (Mw/Mn) of 2.9 was a single peak distribution. Results are shown in Table 6.
  • 22
  • [ 603-76-9 ]
  • [ 48145-04-6 ]
  • [ 1276027-75-8 ]
YieldReaction ConditionsOperation in experiment
93% With indium(III) bromide In 1,2-dichloro-ethane at 80℃; for 12h; Inert atmosphere; regioselective reaction;
  • 23
  • [ 48145-04-6 ]
  • [ 1422263-05-5 ]
YieldReaction ConditionsOperation in experiment
93% With N-iodophthalimide; 3-quinuclidinol In acetonitrile at 20℃; for 24h; Darkness; chemoselective reaction;
  • 24
  • [ 48145-04-6 ]
  • N-(2,4-dimethylphenyl)-N-(2-methylpropyl)-4-[(2-(4-morpholinyl)ethyl)oxy]benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: chlorosulfonic acid / 0 - 20 °C 2.1: pyridine / 20 °C 2.2: 2 h 3.1: potassium iodide; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] / water / 3 h / 150 °C / Microwave irradiation
Multi-step reaction with 4 steps 1: chlorosulfonic acid / dichloromethane / 16.5 h / 0 - 20 °C 2: pyridine / 20 °C 3: lithium hydroxide; water / tetrahydrofuran / 2 h 4: potassium iodide; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] / water / 3 h / 150 °C / Microwave irradiation
  • 25
  • [ 48145-04-6 ]
  • N-(2,4-dimethylphenyl)-4-[(2-hydroxyethyl)oxy]-N-(2-methylpropyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: chlorosulfonic acid / 0 - 20 °C 2.1: pyridine / 20 °C 2.2: 2 h
Multi-step reaction with 3 steps 1: chlorosulfonic acid / dichloromethane / 16.5 h / 0 - 20 °C 2: pyridine / 20 °C 3: lithium hydroxide; water / tetrahydrofuran / 2 h
  • 26
  • [ 48145-04-6 ]
  • 2-[4-(chlorosulfonyl)phenyl]oxy}ethyl 2-propenoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With chlorosulfonic acid at 0 - 20℃; 29 Intermediate 29: 2-jT4-(chlorosulfony0phenyl"loxy ethyl 2-propenoate Intermediate 29: 2-jT4-(chlorosulfony0phenyl"loxy ethyl 2-propenoate A solution of 2-(phenyloxy)ethyl 2-propenoate (5 g, 26.0 mmol) in dichloromethane (50 mL), was cooled to 0 °C. Chlorosulfonic acid (5.21 mL, 78 mmol) was added dropwise over 15 minutes at 0 °C then the mixture was allowed to warm to room temperate over 30 minutes. The reaction mixture was stirred overnight (16 hours) at room temperature. The solution was then poured onto ice and extracted with dichloromethane (3 x 50 mL). Resulting emulsion was diluted with ethyl acetate (200 mL) and brine (50 mL) in order to achieve separation of phases. The aqueous layer was further extracted with ethyl acetate (100 mL). The combined organic fractions were dried with magnesium sulphate then evaporated in vacuo to give an oily solid, which was dried under high vacuum overnight. After drying, a sticky solid was isolated (3.2 g) and this was taken PBb lb/H- on to the next step without further purification. LCMS [LCMS1] Rt 0.47 min, m/z (ES-) 272 (M- CI+OH).
With chlorosulfonic acid In dichloromethane at 0 - 20℃; for 16.5h; Intermediate 29: 2-[4-(chlorosulfonyl)phenyl]oxy}ethyl 2-propenoate A solution of 2-(phenyloxy)ethyl 2-propenoate (5 g, 26.0 mmol) in dichloromethane (50 mL), was cooled to 0° C. Chlorosulfonic acid (5.21 mL, 78 mmol) was added dropwise over 15 minutes at 0° C. then the mixture was allowed to warm to room temperate over 30 minutes. The reaction mixture was stirred overnight (16 hours) at room temperature. The solution was then poured onto ice and extracted with dichloromethane (3×50 mL). Resulting emulsion was diluted with ethyl acetate (200 mL) and brine (50 mL) in order to achieve separation of phases. The aqueous layer was further extracted with ethyl acetate (100 mL). The combined organic fractions were dried with magnesium sulphate then evaporated in vacuo to give an oily solid, which was dried under high vacuum overnight. After drying, a sticky solid was isolated (3.2 g) and this was taken on to the next step without further purification. LCMS [LCMS1] Rt 0.47 min, m/z (ES-) 272 (M-Cl+OH).
  • 27
  • [ 48145-04-6 ]
  • [ 495-48-7 ]
  • [ 1586777-24-3 ]
YieldReaction ConditionsOperation in experiment
81% With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper diacetate In 1,2-dichloro-ethane at 110℃; for 12h; Inert atmosphere;
  • 28
  • [ 48145-04-6 ]
  • 3-(3-aminopropyl)-1-vinyl-2-pyrrolidone [ No CAS ]
  • 3-(3-((3-oxo-3-(2-phenoxyethoxy)propyl)amino)propyl)-1-vinyl-2-pyrrolidone [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With acetic acid In chloroform at 40℃; for 4h;
  • 29
  • [ 48145-04-6 ]
  • MANDELIC ACID [ No CAS ]
  • C29H26O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper diacetate In N,N-dimethyl-formamide at 110℃; for 12h;
  • 30
  • [ 48145-04-6 ]
  • [ 22286-82-4 ]
  • (2Z,4E)-1-ethyl 6-(2-phenoxyethyl) 2-phenylhexa-2,4-dienedioate [ No CAS ]
  • C22H22O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70 % de With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate In 1,4-dioxane at 135℃; for 24h; Sealed tube; Inert atmosphere; Overall yield = 50 %; Overall yield = 36.4 mg; chemoselective reaction;
  • 31
  • [ 48145-04-6 ]
  • C23H29NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: chlorosulfonic acid / dichloromethane / 16.5 h / 0 - 20 °C 2: pyridine / 20 °C
  • 32
  • [ 48145-04-6 ]
  • [ 100-47-0 ]
  • 2-phenoxyethyl (E)-3-(2-cyanophenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; silver(I) acetate In acetic acid at 120℃; for 14h; Inert atmosphere; regioselective reaction;
  • 33
  • [ 1641-09-4 ]
  • [ 48145-04-6 ]
  • bis(2-phenoxyethyl) 3,3'-(3-cyanothiophene-2,4-diyl)(2E,2'E)-diacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate In acetic acid; 1,2-dichloro-ethane at 120℃; for 16h; Inert atmosphere; regioselective reaction;
  • 34
  • [ 371-42-6 ]
  • [ 48145-04-6 ]
  • 2-phenoxyethyl 3-(4-fluorophenylthio)propionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With scandium tris(trifluoromethanesulfonate) In neat (no solvent) at 20℃; for 2h; Green chemistry; regioselective reaction;
  • 35
  • [ 88070-48-8 ]
  • [ 48145-04-6 ]
  • C19H19NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; acetic acid In 1,2-dichloro-ethane at 20℃; for 24h; regioselective reaction;
  • 36
  • [ 48145-04-6 ]
  • 2-phenoxyethyl 2-formyl-2-methyl-5-oxohexanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen; dicarbonylacetylacetonato rhodium (I); 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane / dichloromethane / 5 h / 40 °C / 22502.3 Torr / Autoclave 2: potassium carbonate / dichloromethane / 6 h / 40 °C
  • 37
  • [ 201230-82-2 ]
  • [ 48145-04-6 ]
  • bis(2-phenoxyethyl) 2-formyl-2-methylpentanedioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With dicarbonylacetylacetonato rhodium (I); hydrogen; potassium carbonate; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 50℃; for 18h; Autoclave; Tandem Hydroformylation-Michael Addition Reactions; GeneralProcedure A General procedure: A 4-mL reaction vial with a stirring bar was charged with Rh(acac)(CO)2 (0.5 mg, 2 μmol, 0.2 mol%), dppb (L1, 2.5 mg, 6.0 μmol, 0.6 mol%), and K2CO3 (20 mg, 0.15 mmol, 15 mol%). THF (1 mL) was added by syringe, obtaining a clear yellow dispersion, and finally the acrylate (1.0 mmol) was added to the mixture. The reaction vial was fitted with a hollow screwcap bearing a pierced butadiene-faced septum and placed in a Parr stainless steel autoclave. The atmosphere inside the autoclave was replaced with CO by 3 compression/decompression cycles, and then pressurized with CO/H2 (1:1, 30 bar). The mixture was then stirred at maximum speed at 50 °C for 18 h; afterwards,the autoclave was cooled down to r.t. and decompressed slowly.The obtained dispersion was filtered over a pad of glass fiber, concentratedin vacuo and purified by column chromatography (silicagel, cyclohexane/EtOAc).
  • 38
  • [ 201230-82-2 ]
  • [ 48145-04-6 ]
  • C12H14O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dicarbonylacetylacetonato rhodium (I); hydrogen; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In dichloromethane at 40℃; for 5h; Autoclave; One-Pot Hydroformylation-Michael Addition-Aldol Condensation Reaction; General Procedure B General procedure: A 4-mL reaction vial with a stirring bar was charged with Rh(acac)(CO)2 (0.5 mg, 2 μmol, 0.2 mol%), and MeCgPPh (L6, 1.8 mg,6.0 μmol, 0.6 mol%). CH2Cl2 (1 mL) was added by syringe to give a clear yellow solution, and finally the acrylate (1.0 mmol) was added to the mixture. The reaction vial was fitted with a hollow screwcap bearing a pierced butadiene-faced septum and placed in a Parr stainless steel autoclave. The atmosphere inside the autoclave was replaced with CO by 3 compression/decompression cycles, and then pressurized with CO/H2 (1:1, 30 bar). The mixture was then stirred at maximum speed at 40 °C for 5 h; afterwards, the autoclave was cooled to r.t. and decompressed slowly. Michael acceptor (1 equiv) was added to the product of the hydroformylation step, and finally acatalytic amount of base (15 mol%) was added to the mixture. The reaction vials were closed tightly and stirred at 40 °C for 4-6 h while following the progress of the reaction by TLC. The obtained dispersion was washed with water/CH2Cl2 and the organic phase was concentrated in vacuo and purified by column chromatography (silica gel,cyclohexane/EtOAc).
  • 39
  • [ 13497-18-2 ]
  • [ 48145-04-6 ]
  • 2-phenoxyethyl 3-(bis(3-(triethoxysilyl)propyl)amino)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.6% In ethanol at 20℃; for 8h; Inert atmosphere; 6 Preparation Example 6:
Preparation of 2-phenoxyethyl 3-(bis(3-(triethoxysilyl)propyl)amino)propanoate To a 50 ml, round-bottomed flask, 4.557 mmol of bis(3-triethoxysilylpropyl)amine (Gelest Co.) and 5 ml of ethanol were added for dissolving, and 4.557 mmol of 2-phenoxyethyl acrylate (TCI Co.) was added thereto, followed by stirring at room temperature in nitrogen conditions for 8 hours. After finishing the reaction, solvents were removed under a reduced pressure and distilled at 120° C. under a reduced pressure to obtain 4.17 mmol of a 2-phenoxyethyl 3-(bis(3-(triethoxysilyl)propyl)amino)propanoate compound of Formula (vi) (Yield 91.6%). 1H NMR spectroscopic data of separated 2-phenoxyethyl 3-(bis(3-(triethoxysilyl)propyl)amino)propanoate are as follows. 1H-NMR (500 MHz, CDCl3) δ 7.26-7.23 (m, 2H), δ 6.94-6.84 (m, 3H), δ4.39-4.37 (t, 2H), δ 4.14-4.12 (t, 3H), δ 3.79-3.75 (m, 12H), δ 2.78-2.75 (t, 2H), δ 2.46-2.43 (t, 2H), δ 2.39-2.36 (t, 4H), δ 1.63-1.43 (m, 4H), δ 1.20-1.17 (m, 18H), δ 0.56-0.52 (m, 4H)
  • 40
  • (N-cyclohexylaminomethyl)triethoxysilane [ No CAS ]
  • [ 48145-04-6 ]
  • 2-phenoxyethyl 3-(cyclohexyl((triethoxysilyl)methyl)amino)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.4% In ethanol at 20℃; for 8h; Inert atmosphere; 1 Preparation Example 1:
Preparation of 2-phenoxyethyl 3-(cyclohexyl((triethoxysilyl)methyl)amino)propanoate To a 50 ml, round-bottomed flask, 5.744 mmol of (N-cyclohexylaminomethyl)triethoxysilane (Gelest Co.) and 5 ml of ethanol were added for dissolving, and 5.744 mmol of 2-phenoxyethyl acrylate (TCI Co.) was added thereto, followed by stirring at room temperature in nitrogen conditions for 8 hours. After finishing the reaction, solvents were removed under a reduced pressure and distilled at 120° C. under a reduced pressure to obtain 4.990 mmol of a 2-phenoxyethyl 3-(cyclohexyl((triethoxysilyl)methyl)amino)propanoate compound of Formula (i) (Yield 91.4%). 1H NMR spectroscopic data of separated 2-phenoxyethyl 3-(cyclohexyl((triethoxysilyl)methyl)amino)propanoate are as follows. 1H-NMR (500 MHz, CDCl3) δ 7.49-7.23 (m, 2H), δ 6.97-6.86 (m, 3H), δ 4.40-4.36 (m, 2H), δ 4.16-34.03 (m, 4H), δ 3.87-3.81 (m, 3H), δ 2.78-2.75 (m, 2H), δ 2.50-2.41 (m, 4H), δ 2.17-2.11 (m, 3H), δ 1.72-1.56 (m, 7H), δ 1.26-1.16 (m, 12H)
  • 41
  • [ 492-38-6 ]
  • [ 48145-04-6 ]
  • 2-phenoxyethyl (Z)-(5-oxo-4-phenyl-5H-furan-2-ylidene)acetate [ No CAS ]
  • 2-phenoxyethyl (E)-(5-oxo-4-phenyl-5H-furan-2-ylidene)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 45% 2: 10% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In acetonitrile at 120℃; Inert atmosphere; Sealed tube; Overall yield = 55 %;
  • 42
  • [ 4250-81-1 ]
  • [ 48145-04-6 ]
  • 2-phenoxyethyl 2-phenyl-3-propylcyclobut-2-ene-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With indium tris(trifluoroacetylacetonate); trimethylsilyl bromide In 1,2-dichloro-ethane at 0 - 20℃; for 2h; Inert atmosphere;
  • 43
  • [ 48145-04-6 ]
  • [ 829-48-1 ]
  • 2-phenoxyethyl 2-(3-ethoxy-6-methoxy-1H-isoindol-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 1-Adamantanecarboxylic acid In ethanol at 24℃; for 16h; Schlenk technique; Inert atmosphere;
  • 44
  • [ 48145-04-6 ]
  • ethyl 3,4,5-trimethoxybenzimidate [ No CAS ]
  • 2-phenoxyethyl 2-(3-ethoxy-4,5,6-trimethoxy-1H-isoindol-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 1-Adamantanecarboxylic acid In ethanol at 24℃; for 16h; Schlenk technique; Inert atmosphere;
  • 45
  • [ 48145-04-6 ]
  • [ 103-81-1 ]
  • (E)-2-phenoxyethyl 3-(2-(2-amino-2-oxoethyl)phenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With oxygen; palladium diacetate; trifluoroacetic acid at 100℃; for 36h; regioselective reaction;
  • 46
  • [ 13436-48-1 ]
  • [ 48145-04-6 ]
  • 2-phenoxyethyl (E)-3-(1-methyl-1H-indazol-3-yl)acrylate [ No CAS ]
  • 47
  • [ 5145-65-3 ]
  • [ 48145-04-6 ]
  • 2-phenoxyethyl (E)-3-(1-benzoyl-1H-pyrrol-2-yl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate In toluene at 110℃; for 24h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;
  • 48
  • [ 611-32-5 ]
  • [ 48145-04-6 ]
  • 2-phenoxyethyl 4-(quinolin-8-yl)butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 1,1,1,3',3',3'-hexafluoro-propanol; Trimethylacetic acid at 120℃; for 24h; Inert atmosphere; Glovebox; regioselective reaction;
  • 49
  • [ 22927-13-5 ]
  • [ 48145-04-6 ]
  • phenoxyethyl 3-ethyldihydrocinnamate [ No CAS ]
  • 50
  • [ 48145-04-6 ]
  • [ 5326-06-7 ]
  • (E)-P-ethoxy-P-phenyl-N-(2-phenoxyethyl acrylate) phosphonamide [ No CAS ]
  • (Z)-P-ethoxy-P-phenyl-N-(2-phenoxyethyl acrylate) phosphonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 38% 2: 24% With oxygen; palladium diacetate; copper(I) bromide In tetrahydrofuran at 80℃; for 5h; stereoselective reaction;
1: 24% 2: 38% With oxygen; palladium diacetate; nickel dichloride In tetrahydrofuran at 80℃; for 5h; stereoselective reaction; Typical synthetic procedure of enephosphorylamides 3 General procedure: A Schlenk tube (35 mL) equipped with a magnetic bar was loaded with phosphorylamides 1 (0.5 mmol), NiCl2 (20 mol%) and Pd(OAc)2 (10.0 mol%) in dry THF (5 mL), then alkenes (1.5 mmol, 3.0 Equiv.) were added dropwise and the solution and the mixture were allowed to stir at 80 °C under the O2 for 5 h. After the completion of the reaction (monitored by TLC), the mixture was basified with a diluted Na2CO3 (15 mL) solution and then extracted with dichloromethane (15mL _ 3). The organic phase was combined and then concentrated. The oily crude product was purified by column chromatography using silica gel (200-300 mesh) as a stationary phase and a mixture of petroleum and ethyl acetate as eluent to give the desired product in noted yields.
  • 51
  • [ 48145-04-6 ]
  • cyclobutanone O-(4-(trifluoromethyl)benzoyl) oxime [ No CAS ]
  • [ 104-88-1 ]
  • 2-phenoxyethyl 2-(4-chlorobenzoyl)-6-cyanohexanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With 3-(2,6-diisopropylphenyl)-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate; sodium hydrogencarbonate; magnesium triflate In N,N-dimethyl acetamide; water at 60℃; for 4h; Inert atmosphere;
  • 52
  • [ 644-87-1 ]
  • [ 48145-04-6 ]
  • C15H18O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With triethylamine In acetonitrile at 20℃; for 1h; 4 Example 4: Synthesis of a Dicarboxylic Acid Derived from 2-Phenoxyethyl Acrylate A 250 mL roundbottom flask was charged with mercaptosuccinic acid (12.3 g, 82.0 mmol), 2-phenoxyethyl acrylate (15.0 g, 78.1 mmol), acetonitrile (40 g), and triethylamine (23.7 g, 234 mmol). The solution was stirred at room temperature for 1 hour. The acetonitrile and excess triethylamine were removed by distillation at reduced pressure using a rotary evaporator. The remaining viscous oil was treated with aqueous HC1 (1.0 M, 250 mL) and diethyl ether (200 mL). The mixture was transferred to a separatory funnel and the layers were separated. The organic layer was washed with dilute aqueous HC1 (0.2 M, 200 mL), dried over anhydrous sodium sulfate, and filtered. Concentration at reduced pressure using a rotary evaporator yielded 21.5 g (81% yield) of clear oil that crystallized slowly into a white solid.
  • 53
  • [ 1613-37-2 ]
  • [ 48145-04-6 ]
  • 8-(3-oxo-3-(2-phenoxyethoxy)propyl)quinoline N-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 1-Adamantanecarboxylic acid; silver(I) acetate at 80℃; for 24h; regioselective reaction;
  • 54
  • [ 48145-04-6 ]
  • [ 55-21-0 ]
  • (E)-2-phenoxyethyl 3-(2-carbamoylphenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With silver tetrafluoroborate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate; acetic acid In 1,2-dichloro-ethane at 100℃; for 8h; Sealed tube;
  • 55
  • [ 48145-04-6 ]
  • 2-cyanobenzyl 2-hydroxy-2-phenylacetate [ No CAS ]
  • (E)-2-phenoxyethyl 3-(3-(2-((2-cyanobenzyl)oxy)-1-hydroxy-2-oxoethyl)phenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With silver(I) acetate; palladium diacetate; N-acetylglycine at 90℃; for 24h; Sealed tube;
  • 56
  • [ 48145-04-6 ]
  • methyl(1-(1-phenylvinyl)naphthalen-2-yl)sulfane [ No CAS ]
  • (R)-(2E,4Z)-2-phenoxyethyl 5-(2-(methylthio)naphthalen-1-yl)-5-phenylpenta-2,4-dienoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With silver(I) acetate; palladium diacetate; C47H59O4P In diethyl ether at 60℃; for 24h; Schlenk technique; stereoselective reaction;
  • 57
  • [ 48145-04-6 ]
  • methyl(2-(naphthalen-1-yl)phenyl)sulfane [ No CAS ]
  • 2-phenoxyethyl (E)-3-(1-(2-(methylthio)phenyl)naphthalen-2-yl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With (S)-6,6'-bis(2,4,6-triisopropylphenyl)-1,1'-spirobiindane-7,7'-diyl hydrogenphosphate; silver(I) acetate; palladium diacetate In diethyl ether at 60℃; for 24h; Schlenk technique; enantioselective reaction;
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