8-Methoxy-2-acetamidotetralin

Base Information

• Chemical Name: 8-Methoxy-2-acetamidotetralin
• CAS No.: 153221-21-7
• Molecular Formula: C₁₃H₁₇NO₂
• Molecular Weight: 219.283
• DSSTox Substance ID: DTXSID90934704
• Nikkaji Number: J573.629C
• ChEMBL ID: CHEMBL53015
• Mol file: 153221-21-7.mol

Synonyms:2-acetamido-8-methoxytetralin;2-AMTT;8-methoxy-2-acetamidotetralin;AH 001;AH-001;AH001

Chemical Property of 8-Methoxy-2-acetamidotetralin

Chemical Property:

• Vapor Pressure: 6.24E-08mmHg at 25°C
• Boiling Point: 439.7°Cat760mmHg
• Flash Point: 219.7°C
• PSA: 0.00000
• Density: 1.11g/cm³
• LogP: 0.00000
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 219.125928785
• Heavy Atom Count: 16
• Complexity: 254

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)NC1CCC2=C(C1)C(=CC=C2)OC

Technology Process of 8-Methoxy-2-acetamidotetralin

There total 16 articles about 8-Methoxy-2-acetamidotetralin 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: 91.0%

N-(8-methoxy-3,4-dihydronaphthalen-2-yl)acetamide (1426931-42-1) → (S)-N-(8-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (153221-21-7)

Guidance literature:

With C₅₀H₅₄IrNO₄PSi₂⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen; In dichloromethane; at 23 ℃; for 20h; under 37503.8 Torr; enantioselective reaction;

DOI:10.1021/acscatal.6b01314

Reference yield: 88.0%

N-(8-methoxy-3,4-dihydronaphthalen-2-yl)acetamide (1426931-42-1) → N-(8-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (153221-21-7) + (S)-N-(8-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (153221-21-7)

Guidance literature:

With C₄₅H₆₀NO₄PRh⁽¹⁺⁾*BF₄^(1-); hydrogen; In dichloromethane; at 5 ℃; for 50h; under 7500.75 Torr; Reagent/catalyst; enantioselective reaction; Autoclave;

DOI:10.1002/adsc.201700573

Reference yield: 88.0%

N-(8-methoxy-3,4-dihydronaphthalen-2-yl)acetamide (1426931-42-1) → N-(8-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (153221-21-7) + (S)-N-(8-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (153221-21-7)

Guidance literature:

With C₄₅H₆₀NO₄PRh⁽¹⁺⁾*BF₄^(1-); hydrogen; In dichloromethane; at 5 ℃; for 50h; under 7500.75 Torr; Reagent/catalyst; enantioselective reaction; Autoclave;

DOI:10.1002/adsc.201700573

upstream raw materials:

acetic anhydride

8-Methoxy-(2R)-2-amino-1,2,3,4-tetrahydronaphthalene hydrochloride

8-methoxy-2-aminotetralin

acetyl chloride

Downstream raw materials:

1,2,3,4-tetrahydro-8-methoxy-5-(methylthio)-2-naphthalenamine

Refernces

• 1、 Margalef, Jèssica,Pàmies, Oscar,Diéguez, Montserrat. "Phosphite-Thiother Ligands Derived from Carbohydrates allow the Enantioswitchable Hydrogenation of Cyclic β-Enamides by using either Rh or Ir Catalysts". . p. 813 - 822. Retrieved 2017.
• 2、 Margalef, Jèssica,Biosca, Maria,de la Cruz-Sánchez, Pol,Caldentey, Xisco,Rodríguez-Escrich, Carles,Pàmies, Oscar,Pericàs, Miquel A.,Diéguez, Montserrat. "Indene Derived Phosphorus-Thioether Ligands for the Ir-Catalyzed Asymmetric Hydrogenation of Olefins with Diverse Substitution Patterns and Different Functional Groups". supporting information. p. 4561 - 4574. Retrieved 2021/04/05.
• 3、 Biosca, Maria,Magre, Marc,Pàmies, Oscar,Diéguez, Montserrat. "Asymmetric Hydrogenation of Disubstituted, Trisubstituted, and Tetrasubstituted Minimally Functionalized Olefins and Cyclic β-Enamides with Easily Accessible Ir-P,Oxazoline Catalysts". . p. 10316 - 10320. Retrieved 2018/10/20.