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Chemical Structure| 3050-69-9 Chemical Structure| 3050-69-9

Structure of 3050-69-9

Chemical Structure| 3050-69-9

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Product Details of [ 3050-69-9 ]

CAS No. :3050-69-9
Formula : C8H14O2
M.W : 142.20
SMILES Code : CCCCCC(=O)OC=C
English Name :Vinyl hexanoate
MDL No. :MFCD00048869

Safety of [ 3050-69-9 ]

Application In Synthesis of [ 3050-69-9 ]

* 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 [ 3050-69-9 ]

[ 3050-69-9 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 3050-69-9 ]
  • [ 4169-04-4 ]
  • [ 87860-35-3 ]
  • [ 64658-22-6 ]
  • Hexanoic acid (S)-2-phenoxy-propyl ester [ No CAS ]
  • 2
  • [ 3050-69-9 ]
  • [ 4773-96-0 ]
  • [ 1231632-30-6 ]
  • 3
  • [ 506-03-6 ]
  • [ 3050-69-9 ]
  • [ 1278408-27-7 ]
YieldReaction ConditionsOperation in experiment
91% With Candida antarctica lipase B In dichloromethane at 20℃; for 3h; Enzymatic reaction; regioselective reaction; 4.1.2. Synthesis of (R)-1-O-hexadecyl-3-acetyl-sn-glycerol (4a) General procedure: To a mixture of 1-O-hexadecyl-sn-glycerol 1 (500 mg, 1.58 mmol) and vinyl ethanoate (170 mg, 1.97 mmol) in dichloromethane (5 ml), C. antarctica lipase (67 mg) was added and the resulting mixture stirred for 3 h at room temperature. After filtration of the lipase the reaction solution was concentrated to dryness in vacuo and the residue introduced to crystallization in petroleum ether at -18 °C, affording the product as white crystals (538 mg, 95% yield).
  • 4
  • [ 3050-69-9 ]
  • [ 4753-02-0 ]
  • [ 1609158-55-5 ]
YieldReaction ConditionsOperation in experiment
With Novozym 435 from Candida antarctica In acetone at 40℃; for 11.5h; Enzymatic reaction; regioselective reaction; General procedure for enzymatic acylation of nucleoside General procedure: The solvents were dried by gentle shaking with 4 A molecular sieves overnight. Anhydrous organic solvent (2 mL), nucleoside (0.04 mmol), vinyl ester (0.28 mmol),and Novozym 435 (60 mg) were incubated in a 10-mL Erlenmeyer shaking flask capped with a septum and heated to 40 °C over a water bath. Periodically, aliquotswere withdrawn from the reaction mixture and analyzed by HPLC. No chemical acylation was detectable as confirmed by the control experiments.
  • 5
  • [ 3050-69-9 ]
  • [ 50-90-8 ]
  • [ 1344669-07-3 ]
  • [ 1344669-08-4 ]
YieldReaction ConditionsOperation in experiment
With Novozym 435 from Candida antarctica In acetone at 40℃; for 4h; Enzymatic reaction; regioselective reaction; General procedure for enzymatic acylation of nucleoside General procedure: The solvents were dried by gentle shaking with 4 A molecular sieves overnight. Anhydrous organic solvent (2 mL), nucleoside (0.04 mmol), vinyl ester (0.28 mmol),and Novozym 435 (60 mg) were incubated in a 10-mL Erlenmeyer shaking flask capped with a septum and heated to 40 °C over a water bath. Periodically, aliquotswere withdrawn from the reaction mixture and analyzed by HPLC. No chemical acylation was detectable as confirmed by the control experiments.
  • 6
  • [ 3050-69-9 ]
  • [ 59-14-3 ]
  • [ 123760-37-2 ]
  • [ 123739-80-0 ]
YieldReaction ConditionsOperation in experiment
With Novozym 435 from Candida antarctica In acetone at 40℃; for 3h; Enzymatic reaction; regioselective reaction; General procedure for enzymatic acylation of nucleoside General procedure: The solvents were dried by gentle shaking with 4 A molecular sieves overnight. Anhydrous organic solvent (2 mL), nucleoside (0.04 mmol), vinyl ester (0.28 mmol),and Novozym 435 (60 mg) were incubated in a 10-mL Erlenmeyer shaking flask capped with a septum and heated to 40 °C over a water bath. Periodically, aliquotswere withdrawn from the reaction mixture and analyzed by HPLC. No chemical acylation was detectable as confirmed by the control experiments.
  • 7
  • [ 3050-69-9 ]
  • [ 932398-74-8 ]
  • [ 1211548-71-8 ]
  • [ 2101284-45-9 ]
  • [ 1795771-49-1 ]
YieldReaction ConditionsOperation in experiment
With Novozyme 435 lipase In tert-butyl methyl ether at 30℃; for 8h; Enzymatic reaction; enantioselective reaction;
  • 8
  • [ 3050-69-9 ]
  • [ 100-51-6 ]
  • [ 6938-45-0 ]
YieldReaction ConditionsOperation in experiment
89% With novozyme 435 In toluene at 20℃; for 2h; Enzymatic reaction;
  • 9
  • [ 3050-69-9 ]
  • [ 56552-80-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
94% With Candida antarctica lipase In dichloromethane at 20℃; for 1.5h; Enzymatic reaction; Synthesis of 1-O-Benzyl-3-hexanoyl-sn-glycerol, (R)-5a General procedure: Immobilized CAL-B (18 mg) was added to a solution of 1-O-benzyl-sn-glycerol(150 mg, 0.823 mmol) and vinyl hexanoate (134 mg, 0.940 mmol) in CH2Cl2 (3 mL). The resultingmixture was stirred at room temperature for approx. 90 min when TLC monitoringindicated a complete reaction. The lipase preparation was separated by filtration, and thesolvent was removed in vacuo on a rotary evaporator. The concentrate was applied to a4% boric acid-impregnated flash silica gel chromatography using petroleum ether/ethylacetate (7:3) as the eluent. This afforded the product (R)-5a as a colorless liquid in 94% yield (216 mg, 0.770 mmol). [α]20D = -2.29 (c. 10.0, CH2Cl2). IR (NaCl, νmax/cm-1): 3459(br), 2957 (vs), 2930 (vs), 2861 (vs), 1737 (vs). 1H NMR (400 MHz, CDCl3) δH: 7.38-7.28 (m,5H, Ph-H), 4.56 (s, 2H, PhCH2), 4.19 (dd, J = 11.5, 4.5 Hz, 1H, CH2 sn-3), 4.14 (dd, J = 11.5,6.0 Hz, 1H, CH2 sn-3), 4.05-4.00 (m, 1H, CH sn-2), 3.56 (dd, J = 9.6, 4.3 Hz, 1H, CH2 sn-1),3.50 (dd, J = 9.6, 6.1 Hz, 1H, CH2 sn-1), 2.48 (bs, 1H, OH), 2.32 (t, J = 7.6 Hz, 2H, CH2COO),1.66-1.58 (m, 2H, CH2CH2COO), 1.38-1.24 (m, 4H, CH2), 0.89 (t, J = 6.9 Hz, 3H, CH3) ppm.13C{H} NMR (101 MHz, CDCl3) δC: 174.1, 137.8, 128.6 (2), 128.0, 127.9 (2), 73.6, 71.0, 69.1,65.5, 34.2, 31.4, 24.7, 22.4, 14.0 ppm. HRMS (ESI) m/z: [M + Na]+ calcd for C16H24O4Na303.1567; found, 303.1557.
  • 10
  • [ 3050-69-9 ]
  • [ 17325-85-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
95% With Candida antarctica lipase In dichloromethane at 20℃; for 1.5h; Enzymatic reaction; Synthesis of 3-O-Benzyl-1-hexanoyl-sn-glycerol, (S)-5a General procedure: The same procedure was followed as described for (R)-5a using immobilized CAL-B(6 mg), 3-O-benzyl-sn-glycerol (50 mg, 0.274 mmol), vinyl hexanoate (44 mg, 0.309 mmol)and CH2Cl2 (3 mL). Purification on a 4% boric acid-impregnated flash silica gel chromatographyusing pet. ether/ethyl acetate (7:3) as the eluent afforded the product (S)-5a as acolorless liquid in 95% yield (73 mg, 0.260 mmol). Spectroscopic data identical to those for(R)-5a were obtained. [α]20D = +2.01 (c. 3.6, CH2Cl2). HRMS (ESI) m/z: [M + Na]+ calcd forC16H24O4Na 303.1567; found, 303.1565.
 

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