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[ CAS No. 6880-91-7 ] {[proInfo.proName]}

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Chemical Structure| 6880-91-7
Chemical Structure| 6880-91-7
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Product Details of [ 6880-91-7 ]

CAS No. :6880-91-7 MDL No. :MFCD02183360
Formula : C21H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :ALZAZMCIBRHMFF-UHFFFAOYSA-N
M.W : 349.38 Pubchem ID :485077
Synonyms :
12,13-Dihydrochelerythrine

Safety of [ 6880-91-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6880-91-7 ]

* 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 [ 6880-91-7 ]

[ 6880-91-7 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 32155-84-3 ]
  • [ 6880-91-7 ]
  • 2
  • [ 6880-91-7 ]
  • [ 3895-92-9 ]
YieldReaction ConditionsOperation in experiment
91% A solution of norchelerythrine (1d) (10 mg, 0.03 mmol) in HCO2H (2 mL) was stirred for 12 h, and then NaBH4 (111 mg, 2.93 mmol) was added to the solution at rt. After being stirred at rt for 30 min, the mixture was adjusted to weakly alkaline with an aqueous 10% NaOH and extracted with CHCl3. The CHCl3 layer was washed with water and brine, dried over K2CO3, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 5 g) using EtOAc-hexane (1:19, v/v) as an eluent to give the 5,6-<strong>[6880-91-7]dihydrochelerythrine</strong> (7 mg, 67%), mp 221-224 C (lit.30 mp 220-224 C), which was used to the oxidation step. The Jones reagent (0.063 mL) was added to a stirred solution of the resulting 5,6-<strong>[6880-91-7]dihydrochelerythrine</strong> in acetone (10 mL) under ice-cooling. The mixture was stirred at the same temperature for 30 min, and basified with an aqueous NaOH, which was extracted with CHCl3. The CHCl3 layer was washed with water and brine, dried over K2CO3, and concentrated under reduced pressure. The residue was dissolved in a small amount of CHCl3, and then 10% HCl was added dropwise to the solution under ice-cooling. The resulting precipitates were collected by filtration to give chelerythrine chloride 2d (7 mg, 91%), mp 194-195 C (MeOH-acetone) (lit.30a mp 192-193 C and lit.30b mp 203-206 C). 1H NMR and 13C NMR spectra of synthetic 2d were shown in [Table 7] and [Table 8].
  • 3
  • [ 3895-92-9 ]
  • [ 6880-91-7 ]
YieldReaction ConditionsOperation in experiment
94% With methanol; sodium tetrahydroborate; at 20℃; for 0.5h;Darkness; The compound chelerythrinechloride (120mg, 0.31mmols) was dissolved in 20mL methanol solution, sodium borohydride (100mg, 2.7mmols) was added,After stirring for 30 minutes at room temperature in the dark, stop the reaction and filter with suction.Wash the solid with ultrapure water and methanol, dry in vacuum,The white solid product dihydrochelerythrine (102 mg, yield: 94%) was obtained.
  • 4
  • [ 64-18-6 ]
  • [ 6900-99-8 ]
  • [ 6880-91-7 ]
YieldReaction ConditionsOperation in experiment
67% A solution of norchelerythrine (1d) (10 mg, 0.03 mmol) in HCO2H (2 mL) was stirred for 12 h, and then NaBH4 (111 mg, 2.93 mmol) was added to the solution at rt. After being stirred at rt for 30 min, the mixture was adjusted to weakly alkaline with an aqueous 10% NaOH and extracted with CHCl3. The CHCl3 layer was washed with water and brine, dried over K2CO3, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 5 g) using EtOAc-hexane (1:19, v/v) as an eluent to give the 5,6-dihydrochelerythrine (7 mg, 67%), mp 221-224 C (lit.30 mp 220-224 C), which was used to the oxidation step. The Jones reagent (0.063 mL) was added to a stirred solution of the resulting 5,6-dihydrochelerythrine in acetone (10 mL) under ice-cooling. The mixture was stirred at the same temperature for 30 min, and basified with an aqueous NaOH, which was extracted with CHCl3. The CHCl3 layer was washed with water and brine, dried over K2CO3, and concentrated under reduced pressure. The residue was dissolved in a small amount of CHCl3, and then 10% HCl was added dropwise to the solution under ice-cooling. The resulting precipitates were collected by filtration to give chelerythrine chloride 2d (7 mg, 91%).
  • 5
  • [ 6900-99-8 ]
  • [ 77-78-1 ]
  • [ 6880-91-7 ]
  • 7
  • canadine [ No CAS ]
  • [ 6880-91-7 ]
  • [ 4263-84-7 ]
  • [ 485-91-6 ]
  • 8
  • [ 72584-80-6 ]
  • [ 6880-91-7 ]
  • [ 87972-96-1 ]
  • 9
  • [ 87264-52-6 ]
  • [ 6880-91-7 ]
  • 10
  • (+/-)-cis-N-methyl-7,8,13,13a-tetrahydroberberinium chloride [ No CAS ]
  • [ 6880-91-7 ]
  • [ 485-91-6 ]
  • 11
  • toddalidimerine [ No CAS ]
  • [ 6880-91-7 ]
  • 12
  • [ 485-91-6 ]
  • [ 6880-91-7 ]
YieldReaction ConditionsOperation in experiment
With recombinant Eschscholzia californica P450 CYP82N2v2; NADPH; In aq. buffer; at 30℃;pH 7.6;Enzymatic reaction;Kinetics; General procedure: P6H activity was determined in a reaction mixture that consisted of 50mM Hepes/NaOH (pH 7.6), 500μM NADPH, 10μM substrate, and the enzyme preparation (8.5ng P450). Protopine (5) and allocryptopine (11) were used as standard substrates in the enzymological characterization of CYP82N2v2, and corycavine (15), 13-oxoprotopine (17), protopine N-oxide (18), reticuline (1), scoulerine (2), and N-methyl stylopine (19) were used for the characterization of substrate-specificity. The assay mixture was incubated at 30C for 30min, except for the determination of kinetic parameters (incubation time; 5-10min), and the reaction was then terminated by the addition of Cl3CCO2H (final concentration of 2%) and MeOH (final concentration of 40%). After protein precipitation, the reaction products were determined quantitatively by reversed-phase HPLC with a Shimadzu LC-10 A system: column, COSMOSIL πNAP column (4.6×250mm; Nacalai Tesque); solvent system, 0.05% CF3CO2H/CH3CN containing 0.05% CF3CO2H (1:1); flow rate, 0.5mL/min; detection, absorbance measurement at 280nm with a SPD6A photodiode array detector. Product formation was confirmed by LC-MS (LCMS-2020, Shimadzu; ESI-MS at 70eV, positive ion mode) with the same conditions as in the HPLC analysis except for the solvent system: CH3CN/H2O/AcOH (99:99:2, v/v/v) and flow rate 0.5mL/min.
  • 13
  • chelerythrinium chloride [ No CAS ]
  • [ 6880-91-7 ]
  • 14
  • chelerythrin [ No CAS ]
  • [ 6880-91-7 ]
  • 15
  • O-acetyl-homochelidonine [ No CAS ]
  • [ 6880-91-7 ]
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