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CAS No. : | 15573-67-8 | MDL No. : | MFCD13192798 |
Formula : | C8H6O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KXFJZKUFXHWWAJ-UHFFFAOYSA-N |
M.W : | 166.13 | Pubchem ID : | 355 |
Synonyms : |
4-Hydroxyphenylglyoxylic acid;4-HPGA;4-Hydroxyphenylglyoxylate, 4-Hydroxyphenylglyoxylic acid, para-Hydroxybenzoylformic acid, Pisolithin A
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 40.43 |
TPSA : | 74.6 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.62 cm/s |
Log Po/w (iLOGP) : | 0.6 |
Log Po/w (XLOGP3) : | 0.97 |
Log Po/w (WLOGP) : | 0.66 |
Log Po/w (MLOGP) : | 0.12 |
Log Po/w (SILICOS-IT) : | 0.61 |
Consensus Log Po/w : | 0.59 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.72 |
Solubility : | 3.17 mg/ml ; 0.0191 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.12 |
Solubility : | 1.25 mg/ml ; 0.00751 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.14 |
Solubility : | 12.1 mg/ml ; 0.0729 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.14 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; water at 170℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | With Iodine monochloride; acetic acid at 60℃; for 1h; | |
With hydrogenchloride; Iodine monochloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With aluminium trichloride In dichloromethane at 0 - 20℃; for 24h; | |
With aluminium trichloride; nitrobenzene anschliessendes Erhitzen mit wss. HCl; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With hydrogenchloride for 18h; Heating; | |
With toluene-4-sulfonic acid Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.7 % Chromat. | With calcium hydroxide; water In isopropyl alcohol at 100℃; for 12h; P(CO) = 150 atm at room temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In ethanol for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,6-dimethylpyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; hydrogen 1.) methanol, 3 atm, 45 min, 2.) water, 100 deg C, 4 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide for 4h; Ambient temperature; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In ethyl acetate for 0.25h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid Diazotization; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In ethanol for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In ethanol for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | In ethanol for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-hydroxymandelate oxidase; oxygen; Flavin mononucleotide In various solvent(s) at 25℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With water; sodium hydroxide at 20℃; for 2h; | 1.2 The methyl-4-hydroxyglyoxylate (410 mg, 2.3 mmol) was dissolved in a 2.5 M NaOH solution (20 mL) and the reaction mixture was kept under stirring for 2 hours at room temperature. The reaction mixture was then washed with diethyl ether (2x10 mL) and acidified with concentrated HCI up to pH=2. The aqueous solution was then extracted with ethyl acetate (5x10 mL) and the combined organic phases, washed with brine (2x1 OmL) and dried over anhydrous Na2SC>4. After filtration, the removal of the solvent with the rotary evaporator delivered the 4-hydroxyphenylglyoxalic acid of formula (III) of the title in the form of a yellow solid (310 mg, 83% yield), characterized by comparison with an authentic sample. |
82% | With sodium hydroxide at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: pisolithin A With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0 - 20℃; for 30h; Stage #2: pyrrolidine In tetrahydrofuran at 20 - 50℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 97 percent / HCl / 18 h / Heating 2: 72 percent / 0.17 h / 105 °C / microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 97 percent / HCl / 18 h / Heating 2: 27 percent / 0.17 h / 105 °C / microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 97 percent / HCl / 18 h / Heating 2: 30 percent / 0.17 h / 105 °C / microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 97 percent / HCl / 18 h / Heating 2: 25 percent / 0.17 h / 105 °C / microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 97 percent / HCl / 18 h / Heating 2: 48 percent / 0.17 h / 105 °C / microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 97 percent / HCl / 18 h / Heating 2: 37 percent / 0.17 h / 105 °C / microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 44 percent / aq. glyoxylic acid; copper(II) sulfate; pyridine / 10 h / 20 °C 2: 82 percent / aq. NaOH / 2 h / 20 °C | ||
Multi-step reaction with 2 steps 1: Glyoxilic acid; copper(ll) sulfate pentahydrate; pyridine; acetic acid / water / 10 h / 20 °C 2: sodium hydroxide; water / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 71 percent / ethanol / 2 h / Heating 2: 60 percent / HCl / ethanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 50 percent / ethanol / 2 h / Heating 2: 36 percent / HCl / ethanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / ethanol / 2 h / Heating 2: 37 percent / HCl / ethanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / ethyl acetate / 0.25 h / Ambient temperature 2: hydroxylamine hydrochloride, pyridine / ethanol / 18 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / ethyl acetate / 0.25 h / Ambient temperature 2: hydroxylamine hydrochloride, pyridine / ethanol / 18 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 2 h / Heating 2: aq. NaOH / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 2,6-lutidine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 2,6-lutidine 3: 75 percent / hydroxylamine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium amalgam; water 2: durch Krystallisation des Cinchoninsalzes aus Wasser | ||
99.9 % ee | With (R)-ketoacid reductase from Saccharomyces cerevisiae ZJB5074; glycerol In aq. phosphate buffer at 30℃; Enzymatic reaction; enantioselective reaction; | |
90 % ee | With glucose dehydrogenase; alpha-D-glucopyranose; BgADH2 enzyme; nicotinamide adenine dinucleotide phosphate In water at 30℃; Enzymatic reaction; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; water; ethyl acetate | 74 Preparation 74 Preparation 74 To a solution of N-(4-octyloxybenzoyloxy)phthalimide (4.13 g) in tetrahydrofuran (16 ml) was added hydrazine-hydrate (0.53 ml) at room temperature. After the mixture was stirred at the same temperature for 1 hour, the precipitate was filtered off. To the filtrate was added water (6 ml) and 4-hydroxyphenylglyoxylic acid (1.5 g) at room temperature. The mixture was maintained at pH 4~4.5 with aqueous sodium bicarbonate solution for 2 hours, thereto was added ethyl acetate, and adjusted to pH 2 with 1N hydrochloric acid. The separated organic layer was washed with brine, and dried over magnesium sulfate. The organic solvent was evaporated in vacuo to give (4-hydroxyphenyl)-2-(4-octyloxybenzyloxyimino)acetic acid (3.4 g). IR (Nujol): 3400, 1715, 1605, 1590, 1505 cm-1 NMR (DMSO-d6, δ): 0.86 (3H, m), 1.25 (10H, m), 1.69 (2H, m), 3.94 (2H, t, J=6.4 Hz), 5.07 (2H, s), 6.82 (2H, d, J=8.7 Hz), 6.90 (2H, d, J=8.6 Hz), 7.29 (2H, d, J=8.6 Hz), 7.35 (2H, d, J=8.7 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In 2-methoxy-ethanol; water; dimethyl sulfoxide | 97 PREPARATION OF 4-[[2-(METHOXY)ETHYL]OXY]-ALPHA-OXOBENZENEACETIC ACID EXAMPLE 97 PREPARATION OF 4-[[2-(METHOXY)ETHYL]OXY]-ALPHA-OXOBENZENEACETIC ACID A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid (0.498 g) in dimethylsulfoxide (5 mL) under argon was treated with 4N sodium hydroxide (1.5 mL), stirred for 5 minutes and treated with the mesylate prepared from 2-methoxyethanol (0.462 g). The mixture was heated at 60° C. for 3 hours and poured into excess 1N hydrochloric acid. The product was extracted into diethyl ether (3*50 mL) and the organic layers were washed in turn with water (2*25 mL). The combined organic layers were dried (Na2 SO4), filtered, and evaporated to give 0.56 g of crude product as a solid. Crystallization from ethyl acetate-hexane provided 0.3 g of 4-[[2-(methoxy)ethyl]oxy]-alphaoxobenzeneacetic acid, mp 129°-130° C. Analysis Calculated for C11 H12 O5: C, 58.93; H, 5.39. Found: C, 58.69; H, 5.32. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate In methanol | 5.2 Preparation 5 (2) (a) Phenolphthalein indicator (3 drops) was added to a solution of O-methylhydroxylamine hydrochloride (3.7 g.) in dry methanol (45 ml.). To the solution was dropwise added with stirring at ambient temperature 1 N methanol solution of sodium methoxide (39 ml.) until the color of the solution was changed to purplish red. O-Methylhydroxylamine hydrochloride was added thereto by small portions until the solution was changed to colorless solution. The mixture was stirred for 30 minutes at ambient temperature. After precipitating sodium chloride was filtered off, 2-(4-hydroxyphenyl)glyoxylic acid (6.56 g.) was added to the filtrate and the mixture was stirred for 1 hour at ambient temperature. After methanol was distilled off at low temperature, a saturated sodium chloride aqueous solution was added to the residue. The mixture was adjusted to pH 1 with 10% hydrochloric acid, subjected to salting-out and extracted with ether. The extract was dried over magnesium sulfate. Ether was distilled off at low temperature to give 2-methoxyimino-2-(4-hydroxyphenyl)acetic acid (syn isomer). | |
With sodium methylate In methanol | 5.c.a Preparation 5 (2)(a) Phenolphthalein indicator (3 drops) was added to a solution of O-methylhydroxylamine hydrochloride (3.7 g.) in dry methanol (45 ml.). To the solution was dropwise added with stirring at ambient temperature 1 N methanol solution of sodium methoxide (39 ml.) until the color of the solution was changed to purplish red. O-Methylhydroxylamine hydrochloride was added thereto by small portions until the solutions was changed to colorless solution. The mixture was stirred for 30 minutes at ambient temperature. After precipitating sodium chloride was filtered off, 2-(4-hydroxyphenyl)glyoxylic acid (6.56 g.) was added to the filtrate and the mixture was stirred for 1 hour at ambient temperature. After methanol was distilled off at low temperature, a saturated sodium chloride aqueous solution was added to the residue. The mixture was adjusted to pH 1 with 10% hydrochloric acid, subjected to salting-out and extracted with ether. The extract was dried over magnesium sulfate. Ether was distilled off at low temperature to give 2-methoxyimino-2-(4-hydroxyphenyl)acetic acid (syn isomer). | |
With sodium methylate In methanol | 5.c.a Preparation 5 (2)(a) Phenolphthalein indicator (3 drops) was added to a solution of O-methylhydroxylamine hydrochloride (3.7 g.) in dry methanol (45 ml.). To the solution was dropwise added with stirring at ambient temperature 1 N methanol solution of sodium methoxide (39 ml.) until the color of the solution was changed to purplish red. O-Methylhydroxylamine hydrochloride was added thereto by small portions until the solution was changed to colorless solution. The mixture was stirred for 30 minutes at ambient temperature. After precipitating sodium chloride was filtered off, 2-(4-hydroxyphenyl)glyoxylic acid (6.56 g.) was added to the filtrate and the mixture was stirred for 1 hour at ambient temperature. After methanol was distilled off at low temperature, a saturated sodium chloride aqueous solution was added to the residue. The mixture was adjusted to pH 1 with 10% hydrochloric acid, subjected to salting-out and extracted with ether. The extract was dried over magnesium sulfate. Ether was distilled off at low temperature to give 2-methoxyimino-2-(4-hydroxyphenyl)acetic acid (syn isomer). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With hydrogenchloride; hydroxylamine hydrochloride; sodium chloride In dichloromethane; water | 10 Syn-2-Hydroxyimino-2-(4-hydroxyphenyl)acetic acid. EXAMPLE 10 Syn-2-Hydroxyimino-2-(4-hydroxyphenyl)acetic acid. Magnesium hydroxide (3.8g) was suspended in a solution of 4-hydroxyphenylglyoxylic acid (2.0g) in water (30ml) and a solution of hydroxylamine hydrochloride (1.3g) in water (5ml) was added. The mixture was stirred at room temperature for 6 hrs, cooled in ice and acidified to pH 1.5 under ethyl acetate with 6N HCl. The acidic layer was saturated with NaCl and extracted twice with ethyl acetate. The combined ethyl acetate extracts were washed three times with brine, dried, and evaporated almost to dryness. Addition of dichloromethane gave a buff-coloured solid which was collected, washed with dichloromethane and dried in vacuo to give the title compound (1.66g, 76%) mp 128°-9°; λmax(EtOH) 267.5 nm (ε12,500). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In 1,4-dioxane at 90℃; | 3 As shown in Scheme 8, compound 1002 (58 mg), 4-hydroxyphenylglyoxylic acid (69 mg), 4M HCl-dioxane (0.4 mL), and methanol (4 mL) were mixed together and heated at 90° C. overnight. After cooling, the addition of ether and filtration, compound 103 (0.11 g) was obtained as a yellow solid. To compound 103 (24.4 mg), methanol (2 mL), and 2 drops of concentrated hydrochloric acid was added 10% Pd/C (8 mg). The resulting suspension was stirred under a hydrogen balloon for 24 hours. Filtration through Celite and evaporation under vacuum gave compound 1003 (25 mg). Compound 1003 (20 mg) was refluxed in 6 M hydrochloric acid for 6 hours. Evaporation under vacuum gave the intermediate carboxylic acid, which was dissolved in DMF (2 mL), followed by the addition of 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (40 mg) and diisopropylethylamine (DIEA, 0.02 mL). The resulting mixture was stirred at 40° C. overnight, followed by the addition of water (20 mL) and TFA (0.1 mL). The crude product was extracted with ethyl acetate (3×), dried over Na2SO4, concentrated in vacuo, and purified by HPLC to obtain compound 125. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With silver carbonate In acetonitrile at 60℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With dipotassium peroxodisulfate; iron(III)-acetylacetonate; di-tert-butyl peroxide; In ethyl acetate; at 120℃; for 12h; | Combine 2-(4-hydroxyphenyl)-2-oxoacetic acid (46.8 mg, 0.2 mmol), Fe(acac)3 (21.2 mg, 0.06 mmol), isobutyraldehyde (72.0 mg, 1.0 mmol), DTBP (58.5 mg, 0.4 mmol), K2S2O8 (81.1 mg, 0.3 mmol) and a stirring bar are placed in the reaction tube, and 1 mL of ethyl acetate is added as a solvent, and the reaction tube is closed. Place the reaction tube in an oil bath at 120 C, start stirring, and perform constant temperature reaction for 12 hours. After cooling the reaction mixture to room temperature, the solid residue was filtered through a short silica gel column and washed with 10 mL of ethyl acetate. After evaporating the solvent in vacuo, the crude product was subjected to column chromatography with petroleum ether: ethyl acetate = 4: 1 as the eluent to obtain a pure product. Light yellow liquid, yield 64%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With pyridine; selenium(IV) dioxide at 90 - 110℃; for 4h; Inert atmosphere; | |
With selenium(IV) dioxide In pyridine at 110℃; for 18h; Sealed tube; | 2. Procedure for Preparation of 2b-2l General procedure: A flame-dried pressure tube was charged with the specified acetophenone (4.0 mmol,1.0 equiv.) and selenium dioxide (0.89 g, 8.0 mmol, 2.0 equiv.). Dry pyridine (5 mL)was added, the tube was sealed, and the reaction mixture was heated at 110 °C for 18h. Afterwards, the reaction was cooled to room temperature and filtered. The filtratewas acidified with 1 M HCl solution and extracted three times with EtOAc.Subsequently, the combined organic layers were extracted three times with 1 M NaOHsolution. The combined aqueous layers were acidified with conc. HCl and extractedthree times with EtOAc. The combined organic layers were dried over Na2SO4 andconcentrated in vacuo. Purification by column chromatography yielded the products2b-2l. The characteriza-tion results are consistent with the references. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With (S)-2-amino-(2-chlorophenyl)ethanoic acid In water; acetonitrile at 50℃; for 36h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 98 % ee | With L-glutamic acid; recombinant Pseudomonas stutzeri ST-201 D-phenylglycine aminotransferase; sodium chloride In aq. buffer at 37℃; Enzymatic reaction; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 48h; Inert atmosphere; | 1.3 Step 3: Preparation of (S)-1-(2-(4-hydroxyphenyl)-2-oxoacetyl)-N-(3- phenylpropyl)piperidine-2-carboxamide of formula (IV) 4-hydroxyphenylglyoxalic acid (148 mg, 0.88 mmoles) prepared as above, DIPEA (460 mg, 3.06 mmol) and HATU (410 mg, 1.08 mmol) were added to a solution of (2S)- N-(3-phenylpropyl)piperidine-2-carboxamide (177 mg, 0.72 mmol) in anhydrous DMF (30 ml_), keeping the reaction mixture at a constant temperature of 0 ° C in N2 atmosphere. The reaction mixture has assumed a yellow colour and is kept under stirring at room temperature for 48 hours, maintaining the N2 atmosphere. The reaction mixture was then diluted with ethyl acetate (in 30 ml_) and the phases were allowed to separate; the organic phase was washed with a saturated NH4CI solution and brine (3x 25 ml_), and dried over anhydrous Na2SC>4. The solution was filtered and evaporated with a rotary evaporator until a yellow oil was obtained. The raw thus obtained was purified on chromatographic column with eluent DCM:EtOAc/8:2 so as to obtain (S)-1- (2-(4-hydroxyphenyl)-2-oxoacetyl)-//-(3-phenylpropyl)piperidine-2-carboxamide (190 mg, yield 67%) of the title of formula (IV), in the form of a white solid. NMR, IR and mass spectroscopic analyses provided the following data: 1H NMR, 400MHz, CDCI3, 8:1.25-1.88 (m, 8H, CH2-16 + CH2-8+ CH2-18 + CH2- 18*); 2.22-2.30 (m, 2H, CH2-17); 2.62-2.66 (m, 2H, CH2-7); 2.68-2.76 (m, 2H, CH2-7*); 3.25-3.36 (m, 4H, CH2-9, H-15, H-9*); 3.47-3.50 (m, 1H, H-15); 4.13-4.14 (m, 1H, H- 13*); 4.59-4.63 (m,1 H, H-15*); 5.18 (m, 1H, H-13); 6.33 (bs, 1 H, NH-10); 6.83-6.85 (d, J= 8 Hz, 1 Harom); 6.87-6.90 (d, J=12 Hz, 1Harom); 6.92-6.94 (m, 1Harom); 7.15 (s, 1 H, OHpara); 7.17-7.19 (m, J= 8 Hz, 2Hmeta); 7.24-7.29 (m, 1Harom); 7.80-7.82 (d, J= 8 Hz, 2H Horto). The spectrum1 H-NMR showed the presence of a 1:0.7 mixture of two rotamers. For the signals where the attribution to the different rotamers has been possible, the symbol (*) refers to the minority rotamer. 13C NMR, 100MHz, CDCh, 8:20.21; 20.22; 24.8; 26.29; 26.31 ; 30.90; 30.01; 30.06; 39.56; 44.61; 51.96; 57.06(013); 116.28; 116.34; 125.95; 125.98; 128.12; 128.60; 128.25; 128.29; 128.38; 128.42; 132.41; 132.66; 140.99; 141.07; 168.37 (2C, amide C=0-19, 026); 170.46 (amide C=0 -11); 190.58(ketone C=0). ESI-MS: m/z 417.25 [M+Na]+, 811 [2M+Na]+ (positive mode); 787 [2M-H]~ (negative mode). IR (CDCh), crrf1:3578 (w, NH stretch.), 3315 (w, NH stretch.), 3028 (w, CH stretch.), 2947 (CH stretch.), 1664 (N-C=0 stretch.), 1601 (Ph-C=0 stretch). [a]25D = -7.68°, (c = 40mg in 2mL DCM). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 48 h / 0 - 20 °C / Inert atmosphere 2: dmap; diisopropyl-carbodiimide / N,N-dimethyl-formamide / 24 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 48 h / 0 - 20 °C / Inert atmosphere 2: dmap; diisopropyl-carbodiimide / N,N-dimethyl-formamide / 24 h / 0 - 20 °C 3: triethylsilane; trifluoroacetic acid / N,N-dimethyl-formamide / 0.75 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With tert.-butylhydroperoxide; water; tetra-(n-butyl)ammonium iodide In acetonitrile at 90℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Green chemistry; |
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P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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