Alternatived Products of [ 3895-92-9 ]
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 |
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 ]
- 1
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[ 6880-91-7 ]
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[ 3895-92-9 ]
| Yield | Reaction Conditions | Operation 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]. |
- 2
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[ 3895-92-9 ]
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[ 6880-91-7 ]
| Yield | Reaction Conditions | Operation 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. |
Reference：
[1]Patent: CN111171039,2020,A .Location in patent: Paragraph 0072-0077
[2]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 2002 - 2006
[3]Collection of Czechoslovak Chemical Communications,1977,vol. 42,p. 2686 - 2693
[4]Phytochemistry,1967,vol. 6,p. 1541 - 1550
[5]Collection of Czechoslovak Chemical Communications,1986,vol. 51,p. 2626 - 2634
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