N-[(1R,2R)-1,2,3,4-Tetrahydro-1-hydroxy-7-methoxy-2-naphthalenyl]propanamide

Base Information

• Chemical Name: N-[(1R,2R)-1,2,3,4-Tetrahydro-1-hydroxy-7-methoxy-2-naphthalenyl]propanamide
• CAS No.: 88058-70-2
• Molecular Formula: C₁₄H₁₉NO₃
• Molecular Weight: 249.31
• DSSTox Substance ID: DTXSID70535253
• Wikidata: Q82409460
• Mol file: 88058-70-2.mol

Synonyms:88058-70-2;N-[(1R,2R)-1,2,3,4-TETRAHYDRO-1-HYDROXY-7-METHOXY-2-NAPHTHALENYL]PROPANAMIDE;N-[(1R,2R)-1-hydroxy-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]propanamide;SCHEMBL7272276;DTXSID70535253

Chemical Property of N-[(1R,2R)-1,2,3,4-Tetrahydro-1-hydroxy-7-methoxy-2-naphthalenyl]propanamide

Chemical Property:

• Melting Point: 158-160°C
• PSA: 58.56000
• LogP: 1.96050
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 249.13649347
• Heavy Atom Count: 18
• Complexity: 295

Purity/Quality:

97% ^*data from raw suppliers

N-[(1R,2R)-1,2,3,4-Tetrahydro-1-hydroxy-7-methoxy-2-naphthalenyl]propanamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)NC1CCC2=C(C1O)C=C(C=C2)OC
• Isomeric SMILES: CCC(=O)N[C@@H]1CCC2=C([C@H]1O)C=C(C=C2)OC
• Uses: N-[(1R,2R)-1,2,3,4-Tetrahydro-1-hydroxy-7-methoxy-2-naphthalenyl]propanamide (cas# 88058-70-2) is a compound useful in organic synthesis.

Technology Process of N-[(1R,2R)-1,2,3,4-Tetrahydro-1-hydroxy-7-methoxy-2-naphthalenyl]propanamide

There total 13 articles about N-[(1R,2R)-1,2,3,4-Tetrahydro-1-hydroxy-7-methoxy-2-naphthalenyl]propanamide 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: 87.0%

N-[(1R,2R)-7-Methoxy-1-(3-methoxy-2-oxo-3-phenyl-propyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-propionamide (88336-54-3) → N-<(1R,2R)-1,2,3,4-tetrahydro-1-hydroxy-7-methoxy-2-naphthalenyl>propanamide (88058-70-2,887407-57-0)

Guidance literature:

With potassium hydroxide; In ethanol; water; at 50 ℃; for 0.25h;

DOI:10.1021/jm00378a014

Reference yield:

7-Methoxy-1-tetralone (6836-19-7) → N-<(1R,2R)-1,2,3,4-tetrahydro-1-hydroxy-7-methoxy-2-naphthalenyl>propanamide (88058-70-2,887407-57-0)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium tert-butoxide, isoamyl nitrite / diethyl ether; butan-1-ol / 4 h / Ambient temperature

2: H₂ / 10percent Pd/C / tetrahydrofuran

3: 55 percent / sodium borohydride / ethanol

4: dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / 1 h

5: 87 percent / KOH / ethanol; H₂O / 0.25 h / 50 °C

With dmap; potassium hydroxide; sodium tetrahydroborate; potassium tert-butylate; hydrogen; dicyclohexyl-carbodiimide; isopentyl nitrite; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; water; butan-1-ol;

DOI:10.1021/jm00378a014

Reference yield:

2-hydroximino-7-methoxy-1-tetralone (2471-80-9) → N-<(1R,2R)-1,2,3,4-tetrahydro-1-hydroxy-7-methoxy-2-naphthalenyl>propanamide (88058-70-2,887407-57-0)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / 10percent Pd/C / tetrahydrofuran

2: 55 percent / sodium borohydride / ethanol

3: dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / 1 h

4: 87 percent / KOH / ethanol; H₂O / 0.25 h / 50 °C

With dmap; potassium hydroxide; sodium tetrahydroborate; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; water;

DOI:10.1021/jm00378a014

upstream raw materials:

(+)-trans-2-amino-7-methoxy-1-tetralol

propionic acid anhydride

N-[(1R,2R)-7-Methoxy-1-(3-methoxy-2-oxo-3-phenyl-propyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-propionamide

7-Methoxy-1-tetralone

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