Obaberine

Base Information

• Chemical Name: Obaberine
• CAS No.: 1263-80-5
• Molecular Formula: C₃₈H₄₂N₂O₆
• Molecular Weight: 622.761
• DSSTox Substance ID: DTXSID50155135
• Nikkaji Number: J14.946B
• Wikidata: Q27107561
• Metabolomics Workbench ID: 68053
• ChEMBL ID: CHEMBL464525
• Mol file: 1263-80-5.mol

Synonyms:OBABERINE;(+)-obaberine;1263-80-5;CHEMBL464525;CHEBI:7712;Oxyacanthan, 6,6'7,12'-tetramethoxy-2,2'-dimethyl-;NSC 269190;AC1L2OCJ;6,6',7,12'-tetramethoxy-2,2'-dimethyloxyacanthan;D0P1HA;DTXSID50155135;CHEBI:543003;BDBM50241642;C09596;Q27107561;O(C)c1c(OC)cc2CCN(C)C3Cc4ccc(cc4)Oc5cc(ccc5OC)CC6N(C)CCc7cc(OC)c(Oc1c23)cc67;(1R,14S)-6,20,21,25-tetramethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.29,12.13,7.114,18.027,31.022,33]hexatriaconta-3(36),4,6,9(35),10,12(34),18,20,22(33),24,26,31-dodecaene

Chemical Property of Obaberine

Chemical Property:

• Boiling Point: 710.5oC at 760 mmHg
• Flash Point: 175.8oC
• PSA: 61.86000
• Density: 1.172g/cm3
• LogP: 7.03820
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 622.30428706
• Heavy Atom Count: 46
• Complexity: 979

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C3=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=CC(=C(C=C7CCN6C)OC)O3)OC)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)C[C@@H]6C7=CC(=C(C=C7CCN6C)OC)O3)OC)OC)OC

Technology Process of Obaberine

There total 14 articles about Obaberine 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:

2-benzoyl-6,7,6',12'-tetramethoxy-oxyacanth-1'-ene (61897-94-7) → 6,7,6',12'-tetramethoxy-2,2'-dimethyl-oxyacanthane (1263-80-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄

2: (i) LiAlH₄, AlCl₃, (ii) H₂, Pd-C, (iii) /BRN= 1209228/, (iv) NaBH₄

With sodium tetrahydroborate;

DOI:10.1016/S0040-4039(01)85520-9

Reference yield:

2-benzoyl-6,7,6',12'-tetramethoxy-1',17'-seco-oxyacanthan-1'-one (61897-93-6) → 6,7,6',12'-tetramethoxy-2,2'-dimethyl-oxyacanthane (1263-80-5)

Guidance literature:

Multi-step reaction with 3 steps

1: POCl₃

2: NaBH₄

3: (i) LiAlH₄, AlCl₃, (ii) H₂, Pd-C, (iii) /BRN= 1209228/, (iv) NaBH₄

With sodium tetrahydroborate; trichlorophosphate;

DOI:10.1016/S0040-4039(01)85520-9

Reference yield:

2-benzyl-6,7,6',12'-tetramethoxy-2'-methyl-oxyacanthane (64520-26-9) → 6,7,6',12'-tetramethoxy-2,2'-dimethyl-oxyacanthane (1263-80-5)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd-C / acetic acid

2: methanol; H₂O

With hydrogen; palladium on activated charcoal; In methanol; water; acetic acid;

DOI:10.1248/cpb.25.1636

upstream raw materials:

diazomethane

oxyacanthine

(2²Ξ,4¹S)-1⁴,2⁷,4^6,7-tetramethoxy-2³,4²-dimethyl-2^2,3,4,5,4^1,2,3,4-octahydro-3,7-dioxa-1(1,3),6(1,4)-dibenzena-2(2,8)-benzo[d]azepina-4(8,1)-isoquinolina-cycloheptaphan-2¹-one

formaldehyd

Downstream raw materials:

homoaromoline

aromoline

Refernces

• 1、 Kostalova, Daniela,Uhrin, Dusan,Hrochova, Viera,Tomko, Jozef. "A NEW BISBENZYLISOQUINOLINE ALKALOID FROM Mahonia aquifolium (PURSH) NUTT.". . p. 242 - 246. Retrieved 2007/10/02.
• 2、 Ibuka,Konoshima,Inubushi. "Chemical conversion of stepinonine to bisbenzylisoquinoline alkaloids". . p. 133 - 138. Retrieved 2007/10/04.