(4aS,8aS)-2-Benzoyl-1,3,4,4a,5,8a-hexahydro-6(2H)-isoquinolinone

Base Information

• Chemical Name: (4aS,8aS)-2-Benzoyl-1,3,4,4a,5,8a-hexahydro-6(2H)-isoquinolinone
• CAS No.: 52346-14-2
• Molecular Formula: C16H17NO2
• Molecular Weight: 255.31
• Hs Code.: 2933499090
• European Community (EC) Number: 678-155-4
• DSSTox Substance ID: DTXSID50446919
• Wikidata: Q76416108
• Mol file: 52346-14-2.mol

Synonyms:52346-14-2;(4aS,8aS)-2-Benzoyl-1,3,4,4a,5,8a-hexahydro-6(2H)-isoquinolinone;(4AS,8aS)-2-benzoyl-1,3,4,4a,5,8a-hexahydroisoquinolin-6(2H)-one;(4aS,8aS)-2-benzoyl-1,3,4,4a,5,8a-hexahydroisoquinolin-6-one;2-Benzoyl-1,3,4,4a,5,8a-hexahydro-6(2H)-isoquinolinone;B2360;DTXSID50446919;KIGUODXTRRRCCD-KBPBESRZSA-N;CCA34614;MFCD28990857;AKOS027252975;AS-71731;CS-0453238;D88931;(4aS,8aS)-2-benzoyl-1,2,3,4,4a,5,6,8a-octahydroisoquinolin-6-one

Chemical Property of (4aS,8aS)-2-Benzoyl-1,3,4,4a,5,8a-hexahydro-6(2H)-isoquinolinone

Chemical Property:

• Vapor Pressure: 4.3E-08mmHg at 25°C
• Refractive Index: 1.585
• Boiling Point: 444.4°C at 760 mmHg
• Flash Point: 205.4°C
• PSA: 37.38000
• Density: 1.18g/cm³
• LogP: 2.23180
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 255.125928785
• Heavy Atom Count: 19
• Complexity: 396

Purity/Quality:

98%,99%, ^*data from raw suppliers

(4aS,8aS)-2-Benzoyl-1,3,4,4a,5,8a-hexahydro-6(2H)-isoquinolinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC2C1CC(=O)C=C2)C(=O)C3=CC=CC=C3
• Isomeric SMILES: C1CN(C[C@H]2[C@@H]1CC(=O)C=C2)C(=O)C3=CC=CC=C3

Technology Process of (4aS,8aS)-2-Benzoyl-1,3,4,4a,5,8a-hexahydro-6(2H)-isoquinolinone

There total 6 articles about (4aS,8aS)-2-Benzoyl-1,3,4,4a,5,8a-hexahydro-6(2H)-isoquinolinone 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:

N-benzoylmeroquinene tert-butyl ester (52346-13-1) → 4a(S),8a(R)-2-benzoyl-1,3,4,4a,5,8a-hexahydro-6(2H)-isoquinolinone (52346-14-2)

Guidance literature:

In sulfuric acid; Yield given; 1.) 0 deg C, 30 min; 2.) 20 deg C, 30 min;

DOI:10.1016/S0040-4039(00)73922-0

Reference yield:

quininone (84-31-1) → 4a(S),8a(R)-2-benzoyl-1,3,4,4a,5,8a-hexahydro-6(2H)-isoquinolinone (52346-14-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxygen / tert-butyl alcohol; tetrahydrofuran / 0.25 h / Cooling with ice

1.2: 1.67 h / 20 - 35 °C

2.1: pyridine / dichloromethane / 2.25 h / 20 °C / Reflux; Inert atmosphere

3.1: sulfuric acid / dichloromethane / 2.25 h / 0 - 30 °C / Inert atmosphere

With pyridine; sulfuric acid; oxygen; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;

DOI:10.15227/orgsyn.075.0223

Reference yield:

tert-butyl 2-[(3R,4S)-3-ethenylpiperidin-4-yl]acetate (52346-11-9) → 4a(S),8a(R)-2-benzoyl-1,3,4,4a,5,8a-hexahydro-6(2H)-isoquinolinone (52346-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 2.25 h / 20 °C / Reflux; Inert atmosphere

2: sulfuric acid / dichloromethane / 2.25 h / 0 - 30 °C / Inert atmosphere

With pyridine; sulfuric acid; In dichloromethane;

DOI:10.15227/orgsyn.075.0223

upstream raw materials:

N-benzoylmeroquinene tert-butyl ester

N-benzoyl meroquinene

quininone

tert-butyl 2-[(3R,4S)-3-ethenylpiperidin-4-yl]acetate

Downstream raw materials:

4a(S),8a(R)-2-benzoyloctahydro-6(2H)-isoquinolinone

(4aS,8aR)-2-Benzoyl-1,3,4,4a,5,8a-hexahydro-2H-isoquinolin-6-one