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Palmatine chloride
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Name

Palmatine chloride

 EINECS N/A
CAS No. 10605-02-4 Density 1.25g/cm3
PSA 40.80000 LogP 0.38880
Solubility N/A Melting Point 205℃
Formula C21H22ClNO4 Boiling Point 611.8°C at 760 mmHg
Molecular Weight 387.863 Flash Point 184.1°C
Transport Information N/A Appearance N/A
Safety 24/45 Risk Codes 20/22-36/38
Molecular Structure Molecular Structure of 10605-02-4 (Palmatine chloride) Hazard Symbols N/A
Synonyms

Dibenzo(a,g)quinolizinium, 5,6-dihydro-2,3,9,10-tetramethoxy-, chloride;Palmatine chloride(6CI,7CI);Fibrauretin;

Article Data 7

Palmatine chloride Synthetic route

2-[2-(6,7-dimethoxyisoquinolin-3-yl)-4,5-dimethoxyphenyl]ethanol

10605-02-4

palmatine chloride

Conditions
ConditionsYield
With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 6h;92%
With tetrachloromethane; triphenylphosphine In dichloromethane at 27 - 30℃; for 24h; Inert atmosphere;70%

2-(2-(2-(1,3-dioxolan-2-yl)-3,4-dimethoxyphenyl)acetyl)-4,5-dimethoxyphenethyl pivalate

10605-02-4

palmatine chloride

Conditions
ConditionsYield
Stage #1: 2-(2-(2-(1,3-dioxolan-2-yl)-3,4-dimethoxyphenyl)acetyl)-4,5-dimethoxyphenethyl pivalate With ammonium chloride In ethanol; water at 90 - 110℃; for 56h;
Stage #2: With sodium hydroxide In water for 0.0833333h;		88%
With ammonium chloride In ethanol; water at 90 - 110℃; for 66h; Inert atmosphere;
80-48-8

methyl p-toluene sulfonate

2,3-dihydroxy-9,10-dimethoxy-5,6-dihydro-isoquino[3,2-a]isoquinolinylium chloride

10605-02-4

palmatine chloride

Conditions
ConditionsYield
Stage #1: methyl p-toluene sulfonate; 2,3-dihydroxy-9,10-dimethoxy-5,6-dihydro-isoquino[3,2-a]isoquinolinylium chloride With potassium carbonate In acetonitrile at 80℃; for 12h; Green chemistry;
Stage #2: Reagent/catalyst; Solvent; Temperature; Green chemistry;		80%
77-78-1

dimethyl sulfate

2,3-dihydroxy-9,10-dimethoxy-5,6-dihydro-isoquino[3,2-a]isoquinolinylium chloride

10605-02-4

palmatine chloride

Conditions
ConditionsYield
With potassium carbonate In methanol at 60℃; for 6h;75%

2,3-dihydroxyberberine methanesulfonate

616-38-6

carbonic acid dimethyl ester

10605-02-4

palmatine chloride

Conditions
ConditionsYield
Stage #1: 2,3-dihydroxyberberine methanesulfonate; carbonic acid dimethyl ester With caesium carbonate In N,N-dimethyl-formamide at 140℃; for 8h;
Stage #2: With hydrogenchloride In water for 0.5h; Solvent; Reagent/catalyst;		73.5%

2,3-dihydroxy-9,10-dimethoxy-5,6-dihydro-isoquino[3,2-a]isoquinolinylium chloride

74-88-4

methyl iodide

10605-02-4

palmatine chloride

Conditions
ConditionsYield
With sodium hydroxide In methanol at 25℃; for 6h;60%

2-{[2-(2-hydroxyethyl)-4,5-dimethoxyphenyl]ethynyl}-4,5-dimethoxybenzaldehyde

10605-02-4

palmatine chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: silver nitrate; ammonium acetate / tert-butyl alcohol / 14 h / 27 - 30 °C / Inert atmosphere
2: triphenylphosphine; tetrachloromethane / dichloromethane / 24 h / 27 - 30 °C / Inert atmosphere
View Scheme

2-acetyl-4,5-dimethoxyphenethyl pivalate

2-(6-bromo-2,3-dimethoxyphenyl)-1,3-dioxolane

10605-02-4

palmatine chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) / tetrahydrofuran / 18 h / 90 °C / Inert atmosphere
2: ammonium chloride / water; ethanol / 66 h / 90 - 110 °C / Inert atmosphere
View Scheme
633-65-8

berberine chloride

10605-02-4

palmatine chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: trifluorormethanesulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 0.5 h / 25 °C
1.2: 0 °C
1.3: anion-exchange resin (Cl-)
2.1: potassium carbonate / acetonitrile / 12 h / 80 °C / Green chemistry
2.2: anion-exchange resin (Cl-) / Green chemistry
View Scheme
Multi-step reaction with 2 steps
1.1: trifluorormethanesulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 0.5 h / 25 °C
1.2: 0 °C
1.3: anion-exchange resin (Cl-)
2.1: potassium carbonate / methanol / 6 h / 60 °C
View Scheme
4393-09-3

2,3-dimethoxybenzyl amine

10605-02-4

palmatine chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: C14H22O4Rh / water / 24 h / 100 °C / Sealed tube; Green chemistry
2.1: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] / 2 h / 100 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
3.2: 1 h / 20 °C
View Scheme

Palmatine chloride Specification

The Palmatine chloride, with CAS registry number 10605-02-4, has the systematic name of 2,3,9,10-tetramethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium chloride. This chemical has the related registry number of 3486-67-7 (Parent). And this chemical should be stored in cool, dry place.

Physical properties of Palmatine chloride: (1)ACD/LogP: -1.12; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.12; (4)ACD/LogD (pH 7.4): -1.12; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 5.88; (8)ACD/KOC (pH 7.4): 5.88; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 40.8 Å2.

Uses of Palmatine chloride: it can be used to produce 5,6-dihydro-2,3,8,9-10-pentamethoxydibenzo[a,g]quinolizinium-13-olate. This reaction will need reagents 1 % rose bengal, oxygen and solvent methanol. The reaction time is 20 min with reaction temperature of 0 ℃. The yield is about 60%.

You can still convert the following datas into molecular structure:
(1)SMILES: [Cl-].O(c4cc3c2cc1ccc(OC)c(OC)c1c[n+]2CCc3cc4OC)C
(2)InChI: InChI=1/C21H22NO4.ClH/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4;/h5-6,9-12H,7-8H2,1-4H3;1H/q+1;/p-1
(3)InChIKey: RLQYRXCUPVKSAW-REWHXWOFAH
(4)Std. InChI: InChI=1S/C21H22NO4.ClH/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4;/h5-6,9-12H,7-8H2,1-4H3;1H/q+1;/p-1
(5)Std. InChIKey: RLQYRXCUPVKSAW-UHFFFAOYSA-M

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