Stylopine

Base Information

• Chemical Name: Stylopine
• CAS No.: 4312-32-7
• Molecular Formula: C₁₉H₁₇NO₄
• Molecular Weight: 323.348
• Hs Code.: 2934999090
• NSC Number: 404529,110382
• DSSTox Substance ID: DTXSID50904180
• Nikkaji Number: J263.139C
• Wikipedia: Tetrahydrocoptisine
• Wikidata: Q28603617
• Metabolomics Workbench ID: 131422
• ChEMBL ID: CHEMBL3343660
• Mol file: 4312-32-7.mol

Synonyms:(+-)-tetrahydrocoptisine;(+-)stylopine;(-)-stylopine;(-)-tetrahydrocoptisine;(12bS)-6,7,12b,13-Tetrahydro-4H-bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizine;(S)-stylopine;4H-(1,3)benzodioxolo(5,6-a)-1,3-benzodioxolo(4,5-g)quinolizine, 6,7,12b,13-tetrahydro-;6,7,12b,13-Tetrahydro-4H-bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizine;stylopin;stylopine;stylopine, (S)-isomer;stylopine, 14C-labeled, (+,-)-isomer;tetrahydrocoptisine

Chemical Property of Stylopine

Chemical Property:

• Vapor Pressure: 7E-09mmHg at 25°C
• Melting Point: 221-222℃
• Boiling Point: 466.6°Cat760mmHg
• PKA: 6.53±0.20(Predicted)
• Flash Point: 142.5°C
• PSA: 40.16000
• Density: 1.47g/cm³
• LogP: 2.73740
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 323.11575802
• Heavy Atom Count: 24
• Complexity: 502

Purity/Quality:

99%, ^*data from raw suppliers

Tetrahydrocoptisine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CC3=C(CC2C4=CC5=C(C=C41)OCO5)C=CC6=C3OCO6
• Uses: dl-Stylopineis is an isoquinoline alkaloid isolated from the whole plant of Argemone mexicana. (S)-Stylopine is an important intermediate in the biosynthesis of benzophenanthridine alkaloids, such as Sanguinarine. dl-Stylopineis is an isoquinoline alkaloid isolated from the whole plant of Argemone mexicana. (S)-Stylopine is an important intermediate in the biosynthesis of benzophenanthridine alkaloids, such as Sanguinarine.

Technology Process of Stylopine

There total 82 articles about Stylopine 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: 99.0%

14-bromo-6,7,12b,13-tetrahydro-4H-[1,3]dioxolo[4,5-g][1,3]dioxolo[4',5':7,8]isoquino[3,2-a]isoquinoline (65826-53-1) → Stylopine (84-39-9,2884-83-5,4312-32-7,7461-02-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; triethylamine; In methanol; chloroform; at 20 ℃; for 24h;

Reference yield: 86.0%

(±)-8-oxostylopine (76177-42-9) → Stylopine (84-39-9,2884-83-5,4312-32-7,7461-02-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 0.75h; Heating;

DOI:10.1021/jo982451w

Reference yield: 85.0%

coptisine chloride (6020-18-4) → Stylopine (84-39-9,2884-83-5,4312-32-7,7461-02-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 24h;

DOI:10.1016/S0040-4020(02)00467-2

upstream raw materials:

rac-7-methyl-2,3;9,10-bis-methylenedioxy-berbinium; chloride

14-bromo-6,7,12b,13-tetrahydro-4H-[1,3]dioxolo[4,5-g][1,3]dioxolo[4',5':7,8]isoquino[3,2-a]isoquinoline

coptisine chloride

7,8-methylenedioxy-2-(3,4-methylenedioxyphenethyl)-1,2,3,4-tetrahydroisoquinolin-3-one

Downstream raw materials:

coptisine chloride

corydamine

protopine

Refernces

• 1、 -. "Berberine type alkaloid production (by machine translation)". Paragraph 0076. . Retrieved 2018/05/29.
• 2、 Zhou, Shiqiang,Tong, Rongbiao. "A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps". supporting information. p. 7084 - 7089. Retrieved 2016/05/19.