3-Epi-schelhammericine

Base Information

• Chemical Name: 3-Epi-schelhammericine
• CAS No.: 24204-36-2
• Molecular Formula: C₁₉H₂₃NO₃
• Molecular Weight: 313.397
• NSC Number: 166070
• Nikkaji Number: J16.381C
• Wikidata: Q104394768
• ChEMBL ID: CHEMBL486621
• Mol file: 24204-36-2.mol

Synonyms:NSC166070;3-epi-schelhammericine;CHEMBL486621;NSC-166070;24204-36-2;B602425K093;C-Homoerythrinan,6-didehydro-3-methoxy-15,16-[methylenebis(oxy)]-, (3.beta.)-

Chemical Property of 3-Epi-schelhammericine

Chemical Property:

• Vapor Pressure: 3.36E-08mmHg at 25°C
• Boiling Point: 447.5°Cat760mmHg
• Flash Point: 132.8°C
• PSA: 30.93000
• Density: 1.27g/cm³
• LogP: 2.93560
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 313.16779360
• Heavy Atom Count: 23
• Complexity: 507

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1CC=C2CCN3C2(C1)C4=CC5=C(C=C4CCC3)OCO5
• Isomeric SMILES: CO[C@H]1CC=C2CCN3[C@]2(C1)C4=CC5=C(C=C4CCC3)OCO5
• Description: This epimer of schelhammericine occurs in Phelline comosa. The structure has been deduced from spectroscopic data, particularly from the NMR and mass spectra.

Technology Process of 3-Epi-schelhammericine

There total 54 articles about 3-Epi-schelhammericine 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: 98.0%

(+/-)-8-oxo-schelhemmericine (102487-83-2,102487-84-3) → (+/-)-schelhammericine (21030-78-4,24204-36-2,102487-78-5,102487-79-6)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1248/cpb.33.3574

Reference yield: 94.0%

(+/-)-8-oxo-epischelhemmericine (102487-83-2,102487-84-3) → (+/-)-epischelhammericine (21030-78-4,24204-36-2,102487-78-5,102487-79-6)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1248/cpb.33.3574

Reference yield:

7α-hydroxy-6β-methoxycarbonyl-16,17-methylenedioxy-2,8-dioxo-Δ3-homoerithrinan (89412-91-9) → (+/-)-epischelhammericine (21030-78-4,24204-36-2,102487-78-5,102487-79-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 88 percent / H₂ / 5percent Pd/C / acetone / 6.5 h / Ambient temperature

2: 97 percent / pyridine / 12 h / Ambient temperature

3: 62 percent / DBU / toluene / 2 h / Heating

4: 1.) PhSeCl, BF₃*Et₂O, 2.) MPC / 1.) THF, reflux, 10.5 h 2.) 13 h, RT

5: 96 percent / NaBH₄ / methanol; tetrahydrofuran / 0.75 h / Ambient temperature

6: 1.) NaH, imidazole / 1.) THF, reflux, 3h 2.) 30 min

7: 67 percent / 1.) Bu3SnH, α,α-bisisobutyronitrile 2.) HCl / 1.)toluene, reflux, 5h 2.) 50 deg C, 2.5 h

8: 62 percent / CaCl₂, 3-ethylpentane-3-thiol / dimethylsulfoxide / 1 h / 140 - 145 °C

9: 13 percent / Bu₄NBH₄ / methanol / 1.17 h / 0 °C

10: 1.) NaH, imidazole 2.) Bu₄NHSO₄ / 1.) THF, reflux, 1h 2.) RT, 5h

11: 94 percent / LiAlH₄, AlCl₃ / tetrahydrofuran / 1 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; aluminium trichloride; Phenylselenyl chloride; 2,2'-azobis(isobutyronitrile); 3-ethylpentan-3-yl thiol; boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; tetra(n-butyl)ammonium hydrogensulfate; myristyl-gamma-picolinium chloride; sodium hydride; tetrabutylammonium borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dimethyl sulfoxide; acetone; toluene;

DOI:10.1248/cpb.44.500

upstream raw materials:

3β,15,16-trimethoxy-11a-homo-erythrin-1(6)-en-7ξ-ol

2β-chloro-15,16-methanediyldioxy-3β-methoxy-11a-homo-erythrin-1(6)-ene

homoerythratine

Alkaloid H