(-)-Armepavine

Base Information

• Chemical Name: (-)-Armepavine
• CAS No.: 524-20-9
• Molecular Formula: C19H23NO3
• Molecular Weight: 313.397
• Hs Code.: 2933499090
• UNII: RE6Z59021R
• DSSTox Substance ID: DTXSID901318368
• Nikkaji Number: J869.385D
• Wikidata: Q27105839
• ChEMBL ID: CHEMBL1186510
• Mol file: 524-20-9.mol

Synonyms:armepavine;armepavine, (+-)-isomer;armepavine, (R)-isomer;armepavine, (S)-isomer

Chemical Property of (-)-Armepavine

Chemical Property:

• Vapor Pressure: 4.21E-09mmHg at 25°C
• Melting Point: 149-150°
• Boiling Point: 460.5°Cat760mmHg
• PKA: 9.99±0.15(Predicted)
• Flash Point: 232.3°C
• PSA: 41.93000
• Density: 1.151g/cm³
• LogP: 3.11900
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 313.16779360
• Heavy Atom Count: 23
• Complexity: 370

Purity/Quality:

99%, ^*data from raw suppliers

Armepavine 99.53% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)O)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C=C2[C@H]1CC3=CC=C(C=C3)O)OC)OC

Technology Process of (-)-Armepavine

There total 18 articles about (-)-Armepavine 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:

6,7-dimethoxy-1-[[4-[5-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolinyl)methyl-2-methoxy]phenoxy]benzyl]-2-methyl-1,2,3,4-tetrahydroisoquinoline (228271-22-5) → (S)-armepavine (14400-96-5,3423-14-1) + armepavine (524-20-9,3423-14-1) + (R)-(-)-O-methylarmepavine (3423-02-7,13425-06-4) + (R)-O-methylarmepavine (5701-00-8,13425-06-4)

Guidance literature:

With ammonia; sodium; In 1,4-dioxane; at -78 ℃; for 2h;

DOI:10.1002/ejoc.201301128

Reference yield:

(+/-)-1-(4-hydroxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride + formaldehyd (50-00-0,30525-89-4,61233-19-0) → (S)-armepavine (14400-96-5,3423-14-1) + armepavine (524-20-9,3423-14-1)

Guidance literature:

With sodium acetate; sodium cyanoborohydride; zinc(II) chloride; In methanol; at 20 ℃; for 24h; Overall yield = 96 %; Overall yield = 35.5 mg;

DOI:10.1021/acs.joc.5b00509

Reference yield:

(-)-cycleanine (518-94-5,10438-14-9,18210-67-8,30745-31-4,68778-89-2) → armepavine (524-20-9,3423-14-1)

Guidance literature:

With ammonia; sodium; In toluene; 1) -60 deg C, 3 h, 2) room temperature, 20 h;

DOI:10.1016/S0040-4020(01)81679-3

upstream raw materials:

cycleanine

(-)-cycleanine

N-Norarmepavine

formaldehyd

Downstream raw materials:

2-methylisococlaurine

(R)-O-methylarmepavine

Refernces

• 1、 Kawabata, Yuki,Naito, Yu,Saitoh, Tsuyoshi,Kawa, Kohei,Fuchigami, Toshio,Nishiyama, Shigeru. "Synthesis of (+)-O-methylthalibrine by employing a stereocontrolled Bischler-Napieralski reaction and an electrochemically generated diaryl ether". . p. 99 - 104. Retrieved 2014/01/06.
• 2、 Bhakuni,Dewan S.,Jain,Sudha,Chaturvedi,Rekha. "THE BIOSYNTHESIS OF THE ALKALOIDS OF CISSAMPELOS PAREIRA LINN". . p. 3975 - 3982. Retrieved 2007/10/02.