(4aS,5R,6S,10bS)-5-(naphthalen-2-yl)-6-(2-oxo-2-phenylethyl)-2-phenyl-4a,5,6,10b-tetrahydro-4H-benzo[f]isochromen-4-one

Base Information

• Chemical Name: (4aS,5R,6S,10bS)-5-(naphthalen-2-yl)-6-(2-oxo-2-phenylethyl)-2-phenyl-4a,5,6,10b-tetrahydro-4H-benzo[f]isochromen-4-one
• CAS No.: 1280739-09-4
• Molecular Formula: C₃₇H₂₈O₃
• Molecular Weight: 520.628
• Mol file: 1280739-09-4.mol

Synonyms:

Chemical Property of (4aS,5R,6S,10bS)-5-(naphthalen-2-yl)-6-(2-oxo-2-phenylethyl)-2-phenyl-4a,5,6,10b-tetrahydro-4H-benzo[f]isochromen-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,5R,6S,10bS)-5-(naphthalen-2-yl)-6-(2-oxo-2-phenylethyl)-2-phenyl-4a,5,6,10b-tetrahydro-4H-benzo[f]isochromen-4-one

There total 3 articles about (4aS,5R,6S,10bS)-5-(naphthalen-2-yl)-6-(2-oxo-2-phenylethyl)-2-phenyl-4a,5,6,10b-tetrahydro-4H-benzo[f]isochromen-4-one 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:

3-(naphthalen-2-yl)prop-2-en-1-al (113388-98-0,20884-05-3) + (2E,2′E)-3,3′-(1,2-phenylene)bis(1-phenylprop-2-en-1-one) (156204-13-6) → 5-(naphthalen-2-yl)-6-(2-oxo-2-phenylethyl)-2-phenyl-4a,5,6,10b-tetrahydro-4H-benzo[f]isochromen-4-one + (4aS,5R,6S,10bS)-5-(naphthalen-2-yl)-6-(2-oxo-2-phenylethyl)-2-phenyl-4a,5,6,10b-tetrahydro-4H-benzo[f]isochromen-4-one (1280739-09-4)

Guidance literature:

With 2-(2,4,6-trimethyl-phenyl)-6,10b-dihydro-4H,5aH-5-oxa-3,10c-diaza-2-azonia-cyclopenta[c]fluorene; magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 12h; optical yield given as %ee; stereoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201007144

Reference yield:

(Benzoylmethylene)triphenylphosphorane (20913-05-7,859-65-4) → 5-(naphthalen-2-yl)-6-(2-oxo-2-phenylethyl)-2-phenyl-4a,5,6,10b-tetrahydro-4H-benzo[f]isochromen-4-one + (4aS,5R,6S,10bS)-5-(naphthalen-2-yl)-6-(2-oxo-2-phenylethyl)-2-phenyl-4a,5,6,10b-tetrahydro-4H-benzo[f]isochromen-4-one (1280739-09-4)

Guidance literature:

Multi-step reaction with 2 steps

2: 2-(2,4,6-trimethyl-phenyl)-6,10b-dihydro-4H,5aH-5-oxa-3,10c-diaza-2-azonia-cyclopenta[c]fluorene; magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

With 2-(2,4,6-trimethyl-phenyl)-6,10b-dihydro-4H,5aH-5-oxa-3,10c-diaza-2-azonia-cyclopenta[c]fluorene; magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; 1: Wittig reaction / 2: Michael-type addition;

DOI:10.1002/anie.201007144

Reference yield:

o-phthalic dicarboxaldehyde (643-79-8) → 5-(naphthalen-2-yl)-6-(2-oxo-2-phenylethyl)-2-phenyl-4a,5,6,10b-tetrahydro-4H-benzo[f]isochromen-4-one + (4aS,5R,6S,10bS)-5-(naphthalen-2-yl)-6-(2-oxo-2-phenylethyl)-2-phenyl-4a,5,6,10b-tetrahydro-4H-benzo[f]isochromen-4-one (1280739-09-4)

Guidance literature:

Multi-step reaction with 2 steps

2: 2-(2,4,6-trimethyl-phenyl)-6,10b-dihydro-4H,5aH-5-oxa-3,10c-diaza-2-azonia-cyclopenta[c]fluorene; magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

With 2-(2,4,6-trimethyl-phenyl)-6,10b-dihydro-4H,5aH-5-oxa-3,10c-diaza-2-azonia-cyclopenta[c]fluorene; magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; 1: Wittig reaction / 2: Michael-type addition;

DOI:10.1002/anie.201007144

upstream raw materials:

3-(naphthalen-2-yl)prop-2-en-1-al

(2E,2′E)-3,3′-(1,2-phenylene)bis(1-phenylprop-2-en-1-one)

(Benzoylmethylene)triphenylphosphorane

o-phthalic dicarboxaldehyde