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Chemical Structure| 932398-74-8 Chemical Structure| 932398-74-8

Structure of 932398-74-8

Chemical Structure| 932398-74-8

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Product Details of [ 932398-74-8 ]

CAS No. :932398-74-8
Formula : C14H19NO3
M.W : 249.31
SMILES Code : O=C(N1CCC(O)C2=C1C=CC=C2)OC(C)(C)C
English Name :tert-Butyl 4-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate
MDL No. :MFCD29764361

Safety of [ 932398-74-8 ]

Application In Synthesis of [ 932398-74-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 932398-74-8 ]

[ 932398-74-8 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 1407968-48-2 ]
  • [ 57476-50-3 ]
  • [ 932398-74-8 ]
  • [ 179898-00-1 ]
YieldReaction ConditionsOperation in experiment
1: 26% 2: 31% 3: 11% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; triethylamine In tetrahydrofuran at 110℃; for 24h; Sealed tube; chemoselective reaction;
  • 2
  • [ 9003-20-7 ]
  • [ 932398-74-8 ]
  • [ 1211548-71-8 ]
  • [ 2101284-45-9 ]
  • [ 1795771-46-8 ]
YieldReaction ConditionsOperation in experiment
With lipase RM IM In tert-butyl methyl ether at 30℃; for 8h; Enzymatic reaction;
  • 3
  • [ 9003-20-7 ]
  • [ 932398-74-8 ]
  • [ 1211548-71-8 ]
  • [ 1795771-46-8 ]
YieldReaction ConditionsOperation in experiment
With Novozyme 435 lipase In tert-butyl methyl ether at 30℃; for 8h; Enzymatic reaction; enantioselective reaction;
  • 4
  • [ 9003-20-7 ]
  • [ 932398-74-8 ]
  • [ 1211548-71-8 ]
  • [ 1795771-46-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With Lipase TL IM In tert-butyl methyl ether at 30℃; for 8h; Enzymatic reaction;
  • 5
  • [ 9003-20-7 ]
  • [ 932398-74-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With CAL-A In tert-butyl methyl ether at 30℃; for 8h; Enzymatic reaction;
  • 6
  • [ 2549-51-1 ]
  • [ 932398-74-8 ]
  • [ 1211548-71-8 ]
  • [ 1795771-47-9 ]
YieldReaction ConditionsOperation in experiment
1: 45% 2: 42% With Novozyme 435 lipase In tert-butyl methyl ether at 30℃; for 8h; Enzymatic reaction; enantioselective reaction; 4.2. Representative procedure for the synthesis of (S)-1,2,3,4-tetrahydroquinolin-4-ol (1) and (R)-1,2,3,4-tetrahydroquinolin-4-yl 2-chloroacetate (3) General procedure: To a solution of (rac)-1,2,3,4-tetrahydroquinolin-4-ol (1) (5.00 mmol, 1 equiv) in 50 mL MeOtBu, vinyl 2-chloroacetate (25.00 mmol, 5 equiv) and Novozyme 435 (0.50 g) were consecutively added. The reaction mixture was shaken in orbital shaker at 300 rpm at 30 °C for 8 h. After that, the mixture was filtered and concentrated, and the residue was purified by column chromatography (EtOAc/petroleum = 1:5) to give (S)-1 and (R)-3, respectively.
  • 7
  • [ 10355-48-3 ]
  • [ 932398-74-8 ]
  • [ 1211548-71-8 ]
  • [ 2101284-45-9 ]
  • [ 1795771-48-0 ]
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 ]
  • [ 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;
  • 9
  • [ 20690-63-5 ]
  • [ 932398-74-8 ]
  • [ 1211548-71-8 ]
  • [ 2101284-45-9 ]
  • [ 1795771-50-4 ]
YieldReaction ConditionsOperation in experiment
With Novozyme 435 lipase In tert-butyl methyl ether at 30℃; for 8h; Enzymatic reaction; enantioselective reaction;
  • 10
  • [ 635-46-1 ]
  • [ 932398-74-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 10 h / Reflux 2: potassium permanganate / acetone / 36 h / 25 °C 3: sodium tetrahydroborate / methanol / 0.5 h / 25 °C
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 4 h / 20 - 32 °C 2: cytochrome P450 enzyme CYP102A1 R47L/Y51F/I263A/E267V/I401P mutant; D-glucose; glucose dehydrogenase; C21H25N7O17P3(3-)*2H(1+)*Na(1+) / ethanol; aq. phosphate buffer / 16 h / 20 °C / pH 8.4 / Enzymatic reaction
  • 11
  • [ 123387-53-1 ]
  • [ 932398-74-8 ]
YieldReaction ConditionsOperation in experiment
95% With glucose dehydrogenase; D-glucose; cytochrome P450 enzyme CYP102A1 R47L/Y51F/I263A/E267V/I401P mutant; C21H25N7O17P3(3-)*2H(1+)*Na(1+) In aq. phosphate buffer; ethanol at 20℃; for 16h; Enzymatic reaction;
Multi-step reaction with 2 steps 1: potassium permanganate / acetone / 36 h / 25 °C 2: sodium tetrahydroborate / methanol / 0.5 h / 25 °C
  • 12
  • [ 24424-99-5 ]
  • [ 932398-74-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 10 h / Reflux 2: potassium permanganate / acetone / 36 h / 25 °C 3: sodium tetrahydroborate / methanol / 0.5 h / 25 °C
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 4 h / 20 - 32 °C 2: cytochrome P450 enzyme CYP102A1 R47L/Y51F/I263A/E267V/I401P mutant; D-glucose; glucose dehydrogenase; C21H25N7O17P3(3-)*2H(1+)*Na(1+) / ethanol; aq. phosphate buffer / 16 h / 20 °C / pH 8.4 / Enzymatic reaction
  • 13
  • [ 179898-00-1 ]
  • [ 932398-74-8 ]
YieldReaction ConditionsOperation in experiment
97% With methanol; sodium tetrahydroborate at 0 - 20℃; for 0.666667h; Inert atmosphere;
With sodium tetrahydroborate In methanol at 25℃; for 0.5h;
  • 14
  • [ 9003-20-7 ]
  • [ 932398-74-8 ]
  • [ 1211548-71-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With LPL In tert-butyl methyl ether at 30℃; for 20h; Enzymatic reaction; 2 Example 2 [0056] About 10mg of enzyme shown in the following Table 1 was weighed into a test tube. At the same time, 4mg ofracemic 1-benzyloxycarbonyl-4-hydroxy-1,2,3,4-tetrahydroquinoline and 6mg of vinyl acetate were dissolved in 1mL oftert-butylmethylether. The solution was added to the test tube wherein the enzyme has been weighed in advance, andthe test tube was shaken at 30°C for about 20 hours. The reaction solution was centrifuged, and the supernatant wassampled and subjected to HPLC analysis. HPLC measurement conditionColumn: CHIRALPAK AD-H (4.63250mm)Mobile phase: n-hexane/ethanol=10:1Column temperature: 90°CFlow rate: 1.0mL/minDetection wavelength: 254nm[0057] Retention times of the (S)-4-hydroxy compound, the (R)-4-hydroxy compound and the 4-acetoxy compoundwere 19.6 minute, 26.8 minute, and 9.4 minute, respectively.[0058] The results are shown in Table 1. Conversion ratio (%) means a ratio that the 4-hydroxy compound has beenconverted to the 4-acetoxy compound, and was calculated by the following equation.Optical_A racemic 4-hydroxy-1-tert-butoxycarbonyl-1,2,3,4-tetrahydroquinoline was used as a substrate, and was reacted with the enzymes shown in the following Table 2 in the same manner as Example 1. Results are shown in the following Table 2.
 

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