2H-quinolizin-2-ol, 4-(3,4-dimethoxyphenyl)octahydro-, (2S,4S,9aS)-

Base Information

• Chemical Name: 2H-quinolizin-2-ol, 4-(3,4-dimethoxyphenyl)octahydro-, (2S,4S,9aS)-
• CAS No.: 89771-49-3
• Molecular Formula: C₁₇H₂₅NO₃
• Molecular Weight: 291.39
• DSSTox Substance ID: DTXSID201161768
• Nikkaji Number: J640.751J
• Mol file: 89771-49-3.mol

Synonyms:lasubin I;lasubin II;lasubine II

Chemical Property of 2H-quinolizin-2-ol, 4-(3,4-dimethoxyphenyl)octahydro-, (2S,4S,9aS)-

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 291.18344366
• Heavy Atom Count: 21
• Complexity: 338

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2CC(CC3N2CCCC3)O)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)[C@@H]2C[C@H](C[C@H]3N2CCCC3)O)OC

Technology Process of 2H-quinolizin-2-ol, 4-(3,4-dimethoxyphenyl)octahydro-, (2S,4S,9aS)-

There total 58 articles about 2H-quinolizin-2-ol, 4-(3,4-dimethoxyphenyl)octahydro-, (2S,4S,9aS)- 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: 87.3%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (2R,4R,9aR)-4-(3-Hydroxy-4-methoxy-phenyl)-octahydro-quinolizin-2-ol (52656-92-5,52656-94-7,59373-46-5,66393-21-3,80324-16-9,96684-86-5,96684-87-6) → (±)-lasubine II (89771-49-3)

Guidance literature:

In methanol; at 0 ℃; for 15h;

Reference yield: 83.0%

4-(3,4-dimethoxyphenyl)octahydro-1H-quinolizin-2-yl 4-nitrobenzoate → (±)-lasubine II (89771-49-3)

Guidance literature:

With methanol; potassium carbonate; at 20 ℃; Inert atmosphere;

DOI:10.1002/asia.201501143

Reference yield: 76.0%

(6R*,8R*,9aR*)-6-(3,4-Dimethoxyphenyl)-8-hydroxy-4-quinolizidinone (102734-22-5) → (±)-lasubine II (89771-49-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 4h; Heating;

upstream raw materials:

(4S,9aR)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2-one

4-methoxy-3-(trisopropylsilyl)pyridine

4-lithio-1,2-dimethoxybenzene

4-Methoxy-1-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxycarbonyl]-3-triisopropylsilanyl-pyridinium; chloride

Downstream raw materials:

(+)-subcosine I

2-(p-methoxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine

2-(p-benzyloxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine

Acetic acid (2R,4R,9aR)-4-(3,4-dimethoxy-phenyl)-octahydro-quinolizin-2-yl ester