Structure of 41234-23-5
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CAS No. : | 41234-23-5 |
Formula : | C11H12O4 |
M.W : | 208.21 |
SMILES Code : | O=C(C1C2=CC(OC)=C(OC)C=C2C1)O |
MDL No. : | MFCD09264093 |
* 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 |
---|---|---|
95% | With potassium hydroxide; In ethanol; for 5h;Reflux; | A mixture of 4 (50.0 g, 0.26 mol) and KOH (250.0 g, 4.5mol) in ethanol (1000 mL) was refluxed in a round-bottomed flask for 5 h. The reaction mixture was cooled to room temperature and then water (2500 mL) was added slowly intoreaction flask until it became clear. Ethanol was evaporated off in vacuo, and the residue was acidified to pH 3 with concentrated HCl and extracted with ethyl acetate (500mLx3). The combined extract was dried over anhydrous Na2SO4 and then concentrated in vacuo. The residue was washed with ethyl acetate (200 mL) to yield a white solid of 10 (52.0 g, 95 percent), mp 137?138 C. 1H NMR (300MHz, CDCl3): d3.40 (m, 2H), 3.85 (s, 6H), 4.25 (t, 1H, J3.8 Hz), 6.71 (s, 1H), 6.77 (s, 1H). 13CNMR (100 MHz, CDCl3): 32.4, 46.2, 58.3, 114.5, 115.6, 127.7, 139.8, 148.5, 149.6,178.6. EI-MS m=z 208 (M). Anal. calcd. for C11H12O4: C, 63.45; H, 5.81. Found:C, 63.65; H, 6.01. |
94% | Example 2.Preparation of 3,4-dimethoxy-bicyclo[4.2.0]octa-l ,3,5-triene-7-carboxylic acid(IV)16.4 g (292 mmol) of potassium hydroxide was dissolved in 200 ml of ion exchanged water. 36.78 g (194.4 mmol) of 3,4-dimethoxy-bicyclo[4.2.0]octa-l ,3,5-triene-7-carbonitrile of formula (III) was added to the potassium hydroxide solution. The mixture was refluxed for 4 hours and then cooled to room temperature.6.5 g of Aluminium oxide and 0.70 g of charcoal was added to the stirred mixture. It was stirred for 5 minutes, filtered and washed with 75 ml of ion exchanged water.The filtrate was stirred at room temperature and 27.5 ml (330 mmol) of cc hydrochloric acid was added. The mixture was stirred for 30 minutes at ice- water bath.The precipitated product was filtered, washed with 500 ml of ion exchanged water at 0-5 °C and dried in vacuum at 55 °C.38.0 g of the title compound was obtained in 94percent yield in the form of white, crystalline, racemic carboxylic acid of formula (IV). | |
100%Chromat. | With over-expressed nitrilase of Rhodococcus rhodochrous NCIMB 11216; In aq. phosphate buffer; ethanol; at 30℃; for 2h;pH 7.0;Enzymatic reaction; | Plating on LB+agar+kanamycin, static incubation at 37° C. for 24 hours (strain 11216 of nitrilase of recombinant E. coli). (0112) Preculture in 5 ml of LB+kanamycin (50 mg/1), incubation at 37° C., 180 rpm overnight. Culture: transfer 50 ml of LB and 500 mul of preculture to non-baffled 250-ml Erlenmeyer flasks, incubation at 28° C., 160 rpm until the OD is equal to 0.6 (i.e. about 4 hours). (0113) Induction with IPTG (0.5 mM), incubation at 17° C., 160 rpm overnight (17 hours). (0114) Activity test: centrifuge the cultures at 4° C., 6000 rpm for 20 minutes, resuspend the slurry in 10 ml of 0.1M phosphate buffer pH 7. Add bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile (10 mM)+2percent ethanol. Incubate at 220 rpm, 30° C. (0115) Note: If the culture is more than 50 ml when centrifuging, take off 50 ml and carry out the activity test using a slurry of 50 ml of culture. (0116) Hydrolysis monitoring by chiral chromatography: at 45 mins and 2 hours. Column: Phenomenex® LUNA HST 50*3 C18(2) 2.5 mum Eluant: A+B (from 0percent to 100percent B over 8 mins) A: 1000 water+25 ACN+1 TFA B: 1000 ACN+25 water+1 TFA 0.8 ml/min?40° C.?UV 210 nm Results: Monitoring by chiral chromatography shows that the reaction is not enantioselective. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15%Chromat.; 24%Chromat. | With nitrilase NIT 110; In aq. phosphate buffer; dimethyl sulfoxide; at 28℃; for 72h;pH 7.0;Enzymatic reaction; | Weigh the nitrilase being studied (15 mg), in the form of a lyophilisate, into a tube and then add 4 ml of 0.1M KH2PO4 buffer pH=7 and <strong>[35202-54-1]3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile</strong> (20 mg) dissolved in 100 mul of DMSO. (0090) Place in an incubator at 28° C. and 220 rpm. (0091) The conversion rate was measured by HPLC after 24 hours and 72 hours. (0092) The nitrilases NIT 101, NIT 102, NIT 103, NIT 104, NIT 105, NIT 106, NIT 108, NIT 109, NIT 111, NIT 112 and NIT 113 (Almac) do not hydrolyse the nitrile after 24 hours (no formation of acid or of amide). (0093) The results obtained with the nitrilases NIT 107, NIT 110, NIT 114 and NIT 115 (Almac) are collated in the Table below: The nitrilase NIT 115 was then used in another study to determine if hydrolysis of the nitrile is enantioselective. (0097) The nitrilase NIT 115 (12 mg; Almac) was used in 6 mL [2 mg/mL] of buffer. (0098) 3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile was added to reach a final concentration of 4 mg/mL thereof. (0099) Enantioselectivity was measured by HPLC using the following analytical conditions: Chiralpak IC 250*4.6 column 30percent absolute ethanol+0.1percent TFA+70percent heptane+0.1percent TFA 1 ml/min 30° C. 288 nm Note: Under these conditions, the enantiomers of the acid are separated but not those of the nitrile. (0100) The chromatogram obtained after reacting for 5 hours is shown in FIG. 2. |
47%Chromat.; 7%Chromat. | With nitrilase NIT 115; In aq. phosphate buffer; dimethyl sulfoxide; at 28℃; for 72h;pH 7.0;Enzymatic reaction; | Weigh the nitrilase being studied (15 mg), in the form of a lyophilisate, into a tube and then add 4 ml of 0.1M KH2PO4 buffer pH=7 and <strong>[35202-54-1]3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile</strong> (20 mg) dissolved in 100 mul of DMSO. (0090) Place in an incubator at 28° C. and 220 rpm. (0091) The conversion rate was measured by HPLC after 24 hours and 72 hours. (0092) The nitrilases NIT 101, NIT 102, NIT 103, NIT 104, NIT 105, NIT 106, NIT 108, NIT 109, NIT 111, NIT 112 and NIT 113 (Almac) do not hydrolyse the nitrile after 24 hours (no formation of acid or of amide). (0093) The results obtained with the nitrilases NIT 107, NIT 110, NIT 114 and NIT 115 (Almac) are collated in the Table below: The nitrilase NIT 115 was then used in another study to determine if hydrolysis of the nitrile is enantioselective. (0097) The nitrilase NIT 115 (12 mg; Almac) was used in 6 mL [2 mg/mL] of buffer. (0098) 3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile was added to reach a final concentration of 4 mg/mL thereof. (0099) Enantioselectivity was measured by HPLC using the following analytical conditions: Chiralpak IC 250*4.6 column 30percent absolute ethanol+0.1percent TFA+70percent heptane+0.1percent TFA 1 ml/min 30° C. 288 nm Note: Under these conditions, the enantiomers of the acid are separated but not those of the nitrile. (0100) The chromatogram obtained after reacting for 5 hours is shown in FIG. 2. |
Tags: 41234-23-5 synthesis path| 41234-23-5 SDS| 41234-23-5 COA| 41234-23-5 purity| 41234-23-5 application| 41234-23-5 NMR| 41234-23-5 COA| 41234-23-5 structure
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