Dicentrine

Base Information

• Chemical Name: Dicentrine
• CAS No.: 517-66-8
• Molecular Formula: C20H21 N O4
• Molecular Weight: 339.391
• NSC Number: 406035
• UNII: J2ZGT5M0N7
• DSSTox Substance ID: DTXSID10199651
• Nikkaji Number: J9.429C
• Wikipedia: Dicentrine
• Wikidata: Q15410930
• Metabolomics Workbench ID: 136649
• ChEMBL ID: CHEMBL464748
• Mol file: 517-66-8.mol

Synonyms:(R)-(-)-dicentrine;dicentrine;dicentrine nitrate, (S)-isomer;dicentrine, (-)-;dicentrine, (R)-isomer;L-dicentrine

Chemical Property of Dicentrine

Chemical Property:

• Vapor Pressure: 2.12E-09mmHg at 25°C
• Melting Point: 177-178℃
• Refractive Index: 1.6250 (estimate)
• Boiling Point: 480.7°Cat760mmHg
• PKA: 6.65±0.20(Predicted)
• Flash Point: 142.7°C
• PSA: 40.16000
• Density: 1.266g/cm³
• LogP: 3.12250
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 339.14705815
• Heavy Atom Count: 25
• Complexity: 502

Purity/Quality:

99% ^*data from raw suppliers

Dicentrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C4=C2C1CC5=CC(=C(C=C54)OC)OC)OCO3
• Isomeric SMILES: CN1CCC2=CC3=C(C4=C2[C@@H]1CC5=CC(=C(C=C54)OC)OC)OCO3
• Description: D-Dicentrine is an aporphinic alkaloid found in several plant species, mainly from family Lauraceae, including Lindera megaphylla. D-Dicentrine shows antinociceptive activity in a mouse model of pain. It probably acts via a TRPA1-dependent mechanism. D-Dicentrine is an alpha 1-adrenoceptor antagonist effective against human hyperplastic prostates.
• Uses: d-Dicentrine is a natural aporphine alkaloid extracted from the root of L. megaphylla which displays antitumor effects through inhibition of topoisomerase II.

Technology Process of Dicentrine

There total 14 articles about Dicentrine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 53.0%

(S)-methyl 10,11-dimethoxy-7a,8-dihydro-5H-[1,3]dioxolo[40,5’:4,5]benzo[1,2,3-de]benzo[g]quinoline-7(6H)-carboxylate → (S)-dicentrine (517-66-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2019.130814

Reference yield:

(7aS)-10,11-dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinolin-5c-ol; hydrochloride (72203-90-8) → (S)-dicentrine (517-66-8)

Guidance literature:

With hydrogenchloride; palladium on activated charcoal; In acetic acid; at 50 - 60 ℃; for 4h; under 3102.9 Torr;

Reference yield:

3,4-methylenedioxyphenylethylamine (1484-85-1) → (S)-dicentrine (517-66-8)

Guidance literature:

Multi-step reaction with 6 steps

1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere

2: trifluoromethylsulfonic anhydride; 2-chloropyridine / dichloromethane / 0.25 h / -78 - 0 °C / Inert atmosphere

3: triethylamine; formic acid; Noyori's catalyst / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 10 h / 20 °C / Inert atmosphere

5: palladium diacetate; potassium carbonate; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt / N,N-dimethyl acetamide / 8 h / 130 °C / Inert atmosphere

6: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With 4-methyl-morpholine; 2-chloropyridine; dmap; lithium aluminium tetrahydride; formic acid; Noyori's catalyst; trifluoromethylsulfonic anhydride; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; 2: |Bischler-Napieralski Reaction / 3: |Noyori Asymmetric Hydrogenation;

DOI:10.1016/j.tet.2019.130814

upstream raw materials:

demethyldicentrine

methyl iodide

diazomethane

formaldehyd

Downstream raw materials:

Dehydrodicentrin

Refernces

• 1、 Heng, Hui Li,Chee, Chin Fei,Thy, Chun Keng,Tee, Jia Ti,Chin, Sek Peng,Herr, Deron R.,Buckle, Michael J. C.,Paterson, Ian C.,Doughty, Stephen W.,Abd. Rahman, Noorsaadah,Chung, Lip Yong. "In vitro functional evaluation of isolaureline, dicentrine and glaucine enantiomers at 5-HT2 and α1 receptors". . p. 132 - 138. Retrieved 2018/10/15.
• 2、 Wang,Cheng. "Alkaloids of Illigera luzonensis (Presl) Merr". . p. 1148 - 1150. Retrieved 2007/10/04.