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[ CAS No. 3895-92-9 ] {[proInfo.proName]}

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Chemical Structure| 3895-92-9
Chemical Structure| 3895-92-9
Structure of 3895-92-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3895-92-9 ]

CAS No. :3895-92-9 MDL No. :MFCD00060717
Formula : C21H18ClNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :WEEFNMFMNMASJY-UHFFFAOYSA-M
M.W : 383.82 Pubchem ID :72311
Synonyms :
Chelerythrine (chloride);NSC 646662;Broussonpapyrine chloride
Chemical Name :1,2-Dimethoxy-12-methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-12-ium chloride

Safety of [ 3895-92-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3895-92-9 ]

* 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 [ 3895-92-9 ]

[ 3895-92-9 ] Synthesis Path-Downstream   1~72

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  • [ 6900-99-8 ]
  • [ 77-78-1 ]
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  • 3
  • [ 64-17-5 ]
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  • [ 64-19-7 ]
  • [ 100-63-0 ]
  • 1,2-dimethoxy-12-methyl-13-(<i>N</i>'-phenyl-hydrazino)-12,13-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-<i>c</i>]phenanthridine [ No CAS ]
  • 4
  • [ 64-17-5 ]
  • [ 3895-92-9 ]
  • [ 64-19-7 ]
  • [ 100-63-0 ]
  • 2,3-dimethoxy-6-(5-methylamino-naphtho[2,3-<i>d</i>][1,3]dioxol-6-yl)-benzaldehyde-phenylhydrazone [ No CAS ]
  • 5
  • [ 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-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%), 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].
  • 7
  • [ 3895-92-9 ]
  • [ 78-93-3 ]
  • [ 71627-29-7 ]
  • 8
  • [ 536-75-4 ]
  • [ 3895-92-9 ]
  • (R)-1,2-Dimethoxy-12-methyl-13-((S)-1-pyridin-4-yl-ethyl)-12,13-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine [ No CAS ]
  • (R)-1,2-Dimethoxy-12-methyl-13-((R)-1-pyridin-4-yl-ethyl)-12,13-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine [ No CAS ]
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  • [ 151-50-8 ]
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  • [ 5138-09-0 ]
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  • [ 145654-10-0 ]
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  • [ 3895-92-9 ]
  • [ 4070-42-2 ]
  • bis<6-(5,6-dihydrochelerythrinyl)>ether [ No CAS ]
  • 14
  • [ 3895-92-9 ]
  • [ 71-36-3 ]
  • 6-butoxy-5,6-dihydrochelerythrine [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With sodium hydroxide; In water; at 20℃; for 22.0h;Alkaline aqueous solution; A 0.1 N NaOH solution (1 mL) is added to a suspension of <strong>[3895-92-9]chelerythrine chloride</strong> (30 mg) in 1-butanol (1 mL). The mixture is stirred vigorously at room temperature for 22 h. The white solid is collected by filtration, rinsed with water and dried to afford 6-butoxy-5,6-dihydrochelerythrine (20.3 mg, 62%).
  • 15
  • [ 623-37-0 ]
  • [ 3895-92-9 ]
  • 6-(3-hexoxy)-5,6-dihydrochelerythrine [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With n-butyllithium; In tetrahydrofuran; hexane; water; at 20℃; for 74.0h; N-Butyl Lithium (1.6 M in hexanes, 0.2 mL, 0.32 mmol) is added to a solution of 3-hexanol (31.9 mg, 0.31 mmol) in THF (2 mL). The mixture is stirred for a few minutes followed by addition of <strong>[3895-92-9]chelerythrine chloride</strong> (40 mg, 0.10 mmol). The reaction is stirred for 2 hours and then the solvent is stripped off. The residue is stirred at room temperature in a mixture of water (1 mL) and 3-hexanol (1 mL) for 3 days. The off-white slurry is filtered, rinsed with water and dried to afford 6-(3-hexoxy)-5,6-dihydrochelerythrine (17.4 mg, 37%).
  • 16
  • [ 4897-50-1 ]
  • [ 3895-92-9 ]
  • 6-N-(4-piperidinopiperidin-1-yl)-5,6-dihydrochelerythrine [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% In acetonitrile; at 20℃; A reaction mixture of <strong>[3895-92-9]chelerythrine chloride</strong> (40 mg, 0.10 mmol) and 4-piperidinopiperidine (175 mg, 1.0 rnmol) in acetonitrile (2 mL) is stirred at room temperature overnight. The off-white solid is filtered, washed with acetonitrile and dried to afford 6-N-(4- piperidinopiperidin-lyl)-5,6-dihydrochelerythrine (35.9 mg, 67%).
  • 17
  • [ 111-31-9 ]
  • [ 3895-92-9 ]
  • 6-hexylthio-5,6-dihydrochelerythrine [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With triethylamine; In acetonitrile; at 20℃; for 0.5h; To a yellow suspension of <strong>[3895-92-9]chelerythrine chloride</strong> (30 mg, 0.078 mmol) and 1-hexanethiol (92 mg, 0.78 mmol) in acetonitrile (2 mL) is added a drop of triethylamine. The reaction quickly turns into a colorless solution. The reaction mixture is stirred at room temperature for 30 minutes and then the solvent is removed. The residue is triturated in methanol and filtered. The solid is rinsed with methanol and dried to afford 6- (hexylthio)-5,6-dihydrochelerythrine (10 mg, 28%).
  • 18
  • [ 3895-92-9 ]
  • [ 105-53-3 ]
  • 6-(diethylmalonyl)-5,6-dihydrochelerythrine [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With sodium hydride; In n-heptane; N,N-dimethyl-formamide; mineral oil; at 20℃; Sodium hydride 60% dispersion in mineral oil (10.4 mg, 0.26 mmol,) and anhydrous DMF (5 mL) are placed in a dry reaction vessel. Heptane (3 drops) is then added and the reaction mixture stirred. Diethyl malonate (91.6 mg, 0.57 mmol) is added via a syringe. After the cessation of gas evolution, <strong>[3895-92-9]chelerythrine chloride</strong> (100 mg, 0.26 mmol) is added and the reaction is stirred under nitrogen at room temperature until the yellow color completely disappears. The reaction is quenched by adding ice- water (5 mL). The milky suspension is stirred at room temperature until it became a white suspension. The solid is collected by filtration, rinsed with water and dried to a constant weight to afford the desired chelerythrine diethyl malonate pseudobase (107 mg, 81% yield).
  • 20
  • 6-tert-butoxy-5,6-dihydrochelerythrine [ No CAS ]
  • [ 3895-92-9 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride; at 37℃; for 2.0h;pH ~ 1.2;Simulated Gastric Fluid (SGF);Conversion of starting material; Simulated Gastric Fluid (SGF): Sodium chloride (2 gm), 750 mL distilled water, and 7.0 mL of concentrated hydrochloric acid are added into a 1000 ml volumetric flask. The flask is swirled to mix and the volume brought to 1000 mL with distilled water. The pH should be approx. 1.2.[0137] Simulated Intestinal Fluid (SIF): Monobasic potassium phosphate (6.8 gm) and sodium hydroxide (0.616gm) are added into 250 ml of distilled water in a 1000 ml volumetric flask and swirled until dissolved. 700 ml distilled water is added and the pH checked. The pH is <n="50"/>adjusted to pH 6.8 +/- 0.1 by adding either 0.2N sodium hydroxide or 0.2N hydrochloric acid and the volume is brought to 1000 ml.[0138] General conversion procedure: The pseudobases are placed in SGF or SIF at about 0.2 mg/mL concentration and placed in 37 0C bath with gentle stirring. For those pseudobases which have low aqueous solubility, up to 20% co-solvent such as methanol is added to facilitate dissolution. The progress of the conversion is followed by visual observation (color change) and 1H NMR analysis.[0139] 6-tert-Butoxy-5,6-dihydrochelerythrine (1 mg) is placed in 5 mL of simulated gastric fluid in a glass vial. The vial is gently placed in 37 0C bath with gentle stirring. The solid pseudobase gradually dissolves to give a yellow solution which is the characteristic color of the parent chelerythrine chloride. After 2h, the sample was evaporated to dryness and the residue was dissolved in DMSO-Gk for 1H NMR analysis which showed complete conversion to chelerythrine chloride.[0140] N-(isopropyl)-5.6-dihydrochelerythrine-6-amine (1 mg) is placed in 5 mL of simulated intestinal fluid in a glass vial. The vial is gently placed in 37 0C bath with gentle stirring. The solid pseudobase gradually dissolved to give a yellow solution which is the characteristic color of the parent chelerythrine chloride. After 4h, the sample was evaporated to dryness and the residue was dissolved in DMSO-fc for 1H NMR analysis which showed complete conversion to chelerythrine chloride.[0141] 6-Diethyl-(5,6-dihydrochelerythrine)-malonate (1 mg) is placed in 5 mL of simulated gastric fluid in a glass vial containing 10% methanol. The vial is gently placed in 37 0C bath with gentle stirring. The solid pseudobase gradually dissolves to give a yellow solution which is the characteristic color of the parent chelerythrine chloride. After 16h, the sample was evaporated to dryness and the residue was dissolved in OMSO-ds for 1H NMR analysis which showed complete conversion to chelerythrine chloride.
  • 21
  • 6-(diethylmalonyl)-5,6-dihydrochelerythrine [ No CAS ]
  • [ 3895-92-9 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride; In methanol; water; at 37℃; for 16.0h;pH ~ 1.2;Simulated Gastric Fluid (SGF);Conversion of starting material; Simulated Gastric Fluid (SGF): Sodium chloride (2 gm), 750 mL distilled water, and 7.0 mL of concentrated hydrochloric acid are added into a 1000 ml volumetric flask. The flask is swirled to mix and the volume brought to 1000 mL with distilled water. The pH should be approx. 1.2.[0137] Simulated Intestinal Fluid (SIF): Monobasic potassium phosphate (6.8 gm) and sodium hydroxide (0.616gm) are added into 250 ml of distilled water in a 1000 ml volumetric flask and swirled until dissolved. 700 ml distilled water is added and the pH checked. The pH is <n="50"/>adjusted to pH 6.8 +/- 0.1 by adding either 0.2N sodium hydroxide or 0.2N hydrochloric acid and the volume is brought to 1000 ml.[0138] General conversion procedure: The pseudobases are placed in SGF or SIF at about 0.2 mg/mL concentration and placed in 37 0C bath with gentle stirring. For those pseudobases which have low aqueous solubility, up to 20% co-solvent such as methanol is added to facilitate dissolution. The progress of the conversion is followed by visual observation (color change) and 1H NMR analysis.[0139] 6-tert-Butoxy-5,6-dihydrochelerythrine (1 mg) is placed in 5 mL of simulated gastric fluid in a glass vial. The vial is gently placed in 37 0C bath with gentle stirring. The solid pseudobase gradually dissolves to give a yellow solution which is the characteristic color of the parent chelerythrine chloride. After 2h, the sample was evaporated to dryness and the residue was dissolved in DMSO-Gk for 1H NMR analysis which showed complete conversion to chelerythrine chloride.[0140] N-(isopropyl)-5.6-dihydrochelerythrine-6-amine (1 mg) is placed in 5 mL of simulated intestinal fluid in a glass vial. The vial is gently placed in 37 0C bath with gentle stirring. The solid pseudobase gradually dissolved to give a yellow solution which is the characteristic color of the parent chelerythrine chloride. After 4h, the sample was evaporated to dryness and the residue was dissolved in DMSO-fc for 1H NMR analysis which showed complete conversion to chelerythrine chloride.[0141] 6-Diethyl-(5,6-dihydrochelerythrine)-malonate (1 mg) is placed in 5 mL of simulated gastric fluid in a glass vial containing 10% methanol. The vial is gently placed in 37 0C bath with gentle stirring. The solid pseudobase gradually dissolves to give a yellow solution which is the characteristic color of the parent chelerythrine chloride. After 16h, the sample was evaporated to dryness and the residue was dissolved in OMSO-ds for 1H NMR analysis which showed complete conversion to chelerythrine chloride.
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  • safrole oxide [ No CAS ]
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  • 3-<4-(7-methoxy-2-methyl)benzo<b>furanyl>-1-(3,4-methylenedioxyphenyl)-2-propen-1-one [ No CAS ]
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  • [ 145654-03-1 ]
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  • [ 145654-05-3 ]
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  • cis-2-<4-(7-methoxy-2-methylbenzo<b>furanyl)>-6,7-methylenedioxy-N-methyl-1,2,3,4-tetrahydro-1-naphthylamine [ No CAS ]
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  • [ 145654-04-2 ]
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  • 37
  • cis-2-<4-(7-methoxy-2-methylbenzo<b>furanyl)>-1-(N-methylformamido)-6,7-methylenedioxy-1,2,3,4-tetrahydronaphthalene [ No CAS ]
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  • [ 145654-08-6 ]
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  • [ 18959-63-2 ]
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  • [ 106359-40-4 ]
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  • [ 892150-32-2 ]
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  • 54
  • C19H15NO5 [ No CAS ]
  • [ 3895-92-9 ]
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  • C21H19NO5 [ No CAS ]
  • [ 3895-92-9 ]
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  • [ 56221-41-1 ]
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  • [ 56221-26-2 ]
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  • [ 130260-29-6 ]
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  • [ 49849-13-0 ]
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  • [ 3895-92-9 ]
  • [ 67-63-0 ]
  • 6-isopropoxy-5,6-dihydrochelerythrine [ No CAS ]
  • 63
  • potassium cyanide [ No CAS ]
  • [ 3895-92-9 ]
  • [ 5138-09-0 ]
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  • [ 109-97-7 ]
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