7-Methyl-3-(2-propynyloxy)-4,5,6,7-tetrahydroisothiazolo(4,5-c)pyridine

Base Information

• Chemical Name: 7-Methyl-3-(2-propynyloxy)-4,5,6,7-tetrahydroisothiazolo(4,5-c)pyridine
• CAS No.: 143756-51-8
• Molecular Formula: C₁₀H₁₂N₂OS
• Molecular Weight: 208.284
• DSSTox Substance ID: DTXSID90932008
• Wikidata: Q82907646
• Mol file: 143756-51-8.mol

Synonyms:7-methyl-3-(2-propynyloxy)-4,5,6,7-tetrahydroisothiazolo(4,5-c)pyridine;Lu 26-046;Lu-26-046

Chemical Property of 7-Methyl-3-(2-propynyloxy)-4,5,6,7-tetrahydroisothiazolo(4,5-c)pyridine

Chemical Property:

• Vapor Pressure: 0.00479mmHg at 25°C
• Boiling Point: 276.5°Cat760mmHg
• Flash Point: 121°C
• PSA: 62.39000
• Density: 1.184g/cm³
• LogP: 1.69060
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 208.06703418
• Heavy Atom Count: 14
• Complexity: 250

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CNCC2=C1SN=C2OCC#C
• Isomeric SMILES: C[C@@H]1CNCC2=C1SN=C2OCC#C

Technology Process of 7-Methyl-3-(2-propynyloxy)-4,5,6,7-tetrahydroisothiazolo(4,5-c)pyridine

There total 9 articles about 7-Methyl-3-(2-propynyloxy)-4,5,6,7-tetrahydroisothiazolo(4,5-c)pyridine 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:

(RS)-N-(2-cyanoethyl)-2-methyl-3-aminopropionitrile (120241-52-3) → (R)-(-)-7-methyl-3-propargyl-4,5,6,7-tetrahydroisothiazolo<4,5-c>pyridine (143756-51-8)

Guidance literature:

Multi-step reaction with 9 steps

2: 64 percent / aq. H₂SO₄ / 0.5 h / 60 - 70 °C

3: 88 percent / xylene / 0.75 h / Heating

4: 1.) H₂S, 2.) Br₂ / 1.) DMF, 16 h, 2.) EtOAc, CH₂Cl₂, rt, 16 h

5: HBr / H₂O; acetic acid / 72 h

6: K₂CO₃ / H₂O; tetrahydrofuran / 16 h

7: Bu₄NHSO₄, K₂CO₃ / dimethylformamide / 4 h / 70 °C

8: HCl / diethyl ether / 3 h / Ambient temperature

With hydrogenchloride; sulfuric acid; hydrogen sulfide; hydrogen bromide; bromine; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In tetrahydrofuran; diethyl ether; water; acetic acid; N,N-dimethyl-formamide; xylene;

DOI:10.1016/S0968-0896(99)00033-4

Reference yield:

ethyl rac-3-cyano-5-methyl-4-oxopiperidine-1-carboxylate (243636-70-6) → (R)-(-)-7-methyl-3-propargyl-4,5,6,7-tetrahydroisothiazolo<4,5-c>pyridine (143756-51-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 64 percent / aq. H₂SO₄ / 0.5 h / 60 - 70 °C

2: 88 percent / xylene / 0.75 h / Heating

3: 1.) H₂S, 2.) Br₂ / 1.) DMF, 16 h, 2.) EtOAc, CH₂Cl₂, rt, 16 h

4: HBr / H₂O; acetic acid / 72 h

5: K₂CO₃ / H₂O; tetrahydrofuran / 16 h

6: Bu₄NHSO₄, K₂CO₃ / dimethylformamide / 4 h / 70 °C

7: HCl / diethyl ether / 3 h / Ambient temperature

With hydrogenchloride; sulfuric acid; hydrogen sulfide; hydrogen bromide; bromine; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In tetrahydrofuran; diethyl ether; water; acetic acid; N,N-dimethyl-formamide; xylene;

DOI:10.1016/S0968-0896(99)00033-4

Reference yield:

ethyl (RS)-3-hydroxy-7-methyl-4,5,6,7-tetrahydroisothiazolo<4,5-c>pyridine-5-carboxylate (243636-75-1) → (R)-(-)-7-methyl-3-propargyl-4,5,6,7-tetrahydroisothiazolo<4,5-c>pyridine (143756-51-8)

Guidance literature:

Multi-step reaction with 5 steps

1: HBr / H₂O; acetic acid / 72 h

2: K₂CO₃ / H₂O; tetrahydrofuran / 16 h

3: Bu₄NHSO₄, K₂CO₃ / dimethylformamide / 4 h / 70 °C

4: HCl / diethyl ether / 3 h / Ambient temperature

With hydrogenchloride; hydrogen bromide; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In tetrahydrofuran; diethyl ether; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(99)00033-4

upstream raw materials:

(RS)-7-methyl-3-propargyl-4,5,6,7-tetrahydroisothiazolo<4,5-c>pyridine

(RS)-N-(2-cyanoethyl)-2-methyl-3-aminopropionitrile

ethyl rac-3-cyano-5-methyl-4-oxopiperidine-1-carboxylate

ethyl (RS)-3-hydroxy-7-methyl-4,5,6,7-tetrahydroisothiazolo<4,5-c>pyridine-5-carboxylate

Refernces