Lophocerine

Base Information

• Chemical Name: Lophocerine
• CAS No.: 19485-63-3
• Molecular Formula: C₁₅H₂₃NO₂
• Molecular Weight: 249.353
• DSSTox Substance ID: DTXSID90331794
• Nikkaji Number: J15.900J
• Wikidata: Q27107232
• Metabolomics Workbench ID: 69244
• Mol file: 19485-63-3.mol

Synonyms:Lophocerine;19485-63-3;C09571;AKOS004902384;6-methoxy-2-methyl-1-(2-methylpropyl)-3,4-dihydro-1H-isoquinolin-7-ol;1,2,3,4-Tetrahydro-6-methoxy-2-methyl-1-(2-methylpropyl)isoquinolin-7-ol;AC1L9CKZ;CHEBI:6535;DTXSID90331794;Q27107232;1-isobutyl-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol;6-methoxy-2-methyl-1-(2-methyl-propyl)-1,2,3,4-tetrahydro-isoquinolin-7-ol

Chemical Property of Lophocerine

Chemical Property:

• Vapor Pressure: 1.25E-05mmHg at 25°C
• Boiling Point: 358.3°C at 760 mmHg
• Flash Point: 170.5°C
• PSA: 32.70000
• Density: 1.035g/cm³
• LogP: 2.91380
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 249.172878976
• Heavy Atom Count: 18
• Complexity: 269

Purity/Quality:

99% ^*data from raw suppliers

6-METHOXY-2-METHYL-1-(2-METHYLPROPYL)-3,4-DIHYDRO-1H-ISOQUINOLIN-7-OL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1C2=CC(=C(C=C2CCN1C)OC)O
• Description: This alkaloid belongs to the isoquinoline group and is one of the cactus bases being found in Lophocereus schottii. It is a colourless oil giving a crystalline picrate and a styphnate with m.p. 191.5-193°C and 171-2°C respectively. The structure has been established as 1:2:3:4-tetrahydro-7-hydroxy-l-isobutyl-6- methoxy-2-methylisoquinoline. It yields a methyl ether, forming a picrate, m.p. 180-2°C and a styphnate, m.p. 210-2°C. The corresponding ethyl ether also gives a picrate and styphnate with m.p. ISO-3°C and 182-3°C respectively.

Technology Process of Lophocerine

There total 15 articles about Lophocerine 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: 39.0%

7-benzyloxy-6-methoxy-2-methyl-1-(2-methyl-1-propen-1-yl)-1,2,3,4-tetrahydroisoquinoline (106412-32-2) → Lophocerin (19485-63-3,25181-14-0)

Guidance literature:

With hydrogen; palladium on activated charcoal;

Reference yield:

2-methyl-3-buten-2-ol (115-18-4) → Lophocerin (19485-63-3,25181-14-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 73 percent / triphenylphosphine, Pd(AcO)2 / triethylamine

2: 78 percent / ammonium acetate

3: 81 percent / NaBH₄ / methanol

4: 77 percent / Zn, HCl / methanol

5: 99 percent / CH₂Cl₂; triethylamine

6: 86 percent / LiAlH₄ / tetrahydrofuran

7: 39 percent / H₂ / Pd/C

With ammonium acetate; hydrogenchloride; palladium diacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; triphenylphosphine; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; triethylamine;

Reference yield:

4-benzyloxy-6-bromo-3-methoxybenzaldehyde (40705-22-4) → Lophocerin (19485-63-3,25181-14-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 73 percent / triphenylphosphine, Pd(AcO)2 / triethylamine

2: 78 percent / ammonium acetate

3: 81 percent / NaBH₄ / methanol

4: 77 percent / Zn, HCl / methanol

5: 99 percent / CH₂Cl₂; triethylamine

6: 86 percent / LiAlH₄ / tetrahydrofuran

7: 39 percent / H₂ / Pd/C

With ammonium acetate; hydrogenchloride; palladium diacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; triphenylphosphine; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; triethylamine;

upstream raw materials:

7-benzyloxy-1-isobutyl-6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline

7-benzyloxy-6-methoxy-2-methyl-1-(2-methyl-1-propen-1-yl)-1,2,3,4-tetrahydroisoquinoline

2-methyl-3-buten-2-ol

4-benzyloxy-6-bromo-3-methoxybenzaldehyde

Refernces

• 1、 Yamada, Fumio,Hasegawa, Toshifumi,Wakita, Masayuki,Sugiyama, Mitsuru,Somei, Masanori. "A NOVEL REDUCTIVE AMINO CYCLIZATION METHOD AND ITS APPLICATION FOR THE SYNTHESES OF PYRROLIDINE AND PIPERIDINE NUCLEUS". . p. 1223 - 1226. Retrieved 2007/10/02.