N-Normethylskytanthine

Base Information

• Chemical Name: N-Normethylskytanthine
• CAS No.: 116183-67-6
• Molecular Formula: C₁₀H₁₉N
• Molecular Weight: 153.268
• DSSTox Substance ID: DTXSID40151308
• Wikidata: Q83017747
• Mol file: 116183-67-6.mol

Synonyms:delta-N-normethylskytanthine;N-normethylskytanthine

Chemical Property of N-Normethylskytanthine

Chemical Property:

• Vapor Pressure: 0.294mmHg at 25°C
• Boiling Point: 202.3°Cat760mmHg
• PKA: 11.67±0.60(Predicted)
• Flash Point: 70.4°C
• PSA: 12.03000
• Density: 0.867g/cm³
• LogP: 2.21680
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 153.151749610
• Heavy Atom Count: 11
• Complexity: 144

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C1CNCC2C
• Isomeric SMILES: C[C@@H]1CC[C@@H]2[C@H]1CNC[C@@H]2C

Technology Process of N-Normethylskytanthine

There total 15 articles about N-Normethylskytanthine 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:

(1S,6R,1'S)-5-methyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>non-7-en-4-one (139025-15-3,139069-01-5) → (-)-δ-N-Normethylskytanthine (116183-67-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 3-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / -18 °C

2: 1) Et₂NH, BuLi / 1) Et₂O, hexane, ice-bath, 10 min, 2) Et₂O, r.t., overnight

3: 1) DMSO, oxalyl chloride, 2) Et₃N / 1) CH₂Cl₂, -60 deg C, 45 min, 2) CH₂Cl₂, -50 to -60 deg C, 45 min

4: 90 percent / HMPA, LDA / tetrahydrofuran / 2 h / -80 - -30 °C

5: 22 percent / Zn / acetic acid / 20 h / Heating

6: 81 percent / BF₃*Et₂O / CHCl₃ / 6 h / 0 °C

7: 90 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

8: 2) H₂ / 1) Raney-Ni, 2) 10percent Pd/C / 1) EtOH, reflux, 5 h, 2) AcOH, 70 psi, 45 deg C, 20 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; sodium hydrogencarbonate; dimethyl sulfoxide; diethylamine; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; lithium diisopropyl amide; palladium on activated charcoal; nickel; In tetrahydrofuran; dichloromethane; chloroform; acetic acid;

DOI:10.1002/hlca.19930760416

Reference yield:

(-)-(1R,5R,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)spiro<<3>azabicyclo<4.3.0>nonane-8,2''-<1.3>dithiane>-4-one (139025-21-1) → (-)-δ-N-Normethylskytanthine (116183-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

2: 2) H₂ / 1) Raney-Ni, 2) 10percent Pd/C / 1) EtOH, reflux, 5 h, 2) AcOH, 70 psi, 45 deg C, 20 h

With lithium aluminium tetrahydride; hydrogen; palladium on activated charcoal; nickel; In tetrahydrofuran;

DOI:10.1002/hlca.19930760416

Reference yield:

(-)-(1S,5R,6R,7R,8S,1'S)-7,8-epoxy-5-methyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4-one (139025-16-4) → (-)-δ-N-Normethylskytanthine (116183-67-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) Et₂NH, BuLi / 1) Et₂O, hexane, ice-bath, 10 min, 2) Et₂O, r.t., overnight

2: 1) DMSO, oxalyl chloride, 2) Et₃N / 1) CH₂Cl₂, -60 deg C, 45 min, 2) CH₂Cl₂, -50 to -60 deg C, 45 min

3: 90 percent / HMPA, LDA / tetrahydrofuran / 2 h / -80 - -30 °C

4: 22 percent / Zn / acetic acid / 20 h / Heating

5: 81 percent / BF₃*Et₂O / CHCl₃ / 6 h / 0 °C

6: 90 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

7: 2) H₂ / 1) Raney-Ni, 2) 10percent Pd/C / 1) EtOH, reflux, 5 h, 2) AcOH, 70 psi, 45 deg C, 20 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; dimethyl sulfoxide; diethylamine; triethylamine; zinc; lithium diisopropyl amide; palladium on activated charcoal; nickel; In tetrahydrofuran; chloroform; acetic acid;

DOI:10.1002/hlca.19930760416

upstream raw materials:

(+)-(1R,5R,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)spiro<<3>azabicyclo<4.3.0>nonane-8,2''-<1,3>dithiane>

(1S,6R,1'S)-5-methyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>non-7-en-4-one

(-)-(1R,5R,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)spiro<<3>azabicyclo<4.3.0>nonane-8,2''-<1.3>dithiane>-4-one

(-)-(1S,5R,6R,7R,8S,1'S)-7,8-epoxy-5-methyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4-one

Refernces

• 1、 Cid, M. M.,Eggnauer, U.,Weber, H. P.,Pombo-Villar, E.. "Synthesis of (-)-δ-N-Normethylskytanthine". . p. 7233 - 7236. Retrieved 2007/10/02.