Sinococuline

Base Information

• Chemical Name: Sinococuline
• CAS No.: 109351-36-2
• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.384
• UNII: J5624PB437
• DSSTox Substance ID: DTXSID00911127
• Wikipedia: Sinococuline
• Wikidata: Q15427859
• ChEMBL ID: CHEMBL524026
• Mol file: 109351-36-2.mol

Synonyms:sinococuline

Chemical Property of Sinococuline

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 562.7°Cat760mmHg
• PKA: 9.90±0.70(Predicted)
• Flash Point: 294.1°C
• PSA: 91.18000
• Density: 1.41g/cm³
• LogP: 0.91140
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 333.15762283
• Heavy Atom Count: 24
• Complexity: 538

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C(CC3C4=C(C(C(CC42CCN3)O)O)OC)C=C1)O
• Isomeric SMILES: COC1=C(C2=C(C[C@H]3C4=C([C@H]([C@H](C[C@]42CCN3)O)O)OC)C=C1)O

Technology Process of Sinococuline

There total 5 articles about Sinococuline 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: 95.0%

(6S,7S,9S,13S)-8,14-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,8-dimethoxymorphinane-6,7-diol (160694-06-4) → Sinococuline (109351-36-2)

Guidance literature:

palladium dihydroxide; In ethanol; cyclohexene; for 4.5h; Heating;

DOI:10.1039/c39940002707

Reference yield:

(6S,9S,13S)-8,14-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-6-<(tert-butyldimethylsilyl)oxy>-3,8-dimethoxymorphinan-7-one (160694-04-2) → Sinococuline (109351-36-2)

Guidance literature:

Multi-step reaction with 3 steps

1: LiBEt₃H / tetrahydrofuran / 3 h / -78 °C

2: p-TsOH*H₂O / tetrahydrofuran; H₂O / 96 h / Ambient temperature

3: 95 percent / Pd(OH)2/C / cyclohexene; ethanol / 4.5 h / Heating

With lithium triethylborohydride; toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; ethanol; water; cyclohexene;

DOI:10.1039/c39940002707

Reference yield:

(6S,7S,9S,13S)-8,14-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-6-<(tert-butyldimethylsilyl)oxy>-3,8-dimethoxymorphinan-7-ol (160694-05-3) → Sinococuline (109351-36-2)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH*H₂O / tetrahydrofuran; H₂O / 96 h / Ambient temperature

2: 95 percent / Pd(OH)2/C / cyclohexene; ethanol / 4.5 h / Heating

With toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; ethanol; water; cyclohexene;

DOI:10.1039/c39940002707

upstream raw materials:

cephamorphinanine

(6S,7S,9S,13S)-8,14-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,8-dimethoxymorphinane-6,7-diol

(6S,9S,13S)-8,14-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-6-<(tert-butyldimethylsilyl)oxy>-3,8-dimethoxymorphinan-7-one

(6S,7S,9S,13S)-8,14-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-6-<(tert-butyldimethylsilyl)oxy>-3,8-dimethoxymorphinan-7-ol

Refernces

• 1、 Hitotsuyanagi, Yukio,Nishimura, Kunihiko,Ikuta, Hiroshi,Takeya, Koichi,Itokawa, Hideji. "Syntheses of Antitumor Morphinane Alkaloids, Sinococuline and 6-epi-, 7-epi-, and 6-epi-7-epi-Sinococuline, from Sinomenine". . p. 4549 - 4558. Retrieved 2007/10/02.