3-benzyloxy-13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-7,8-dihydro-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one

Base Information

• Chemical Name: 3-benzyloxy-13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-7,8-dihydro-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one
• CAS No.: 895632-74-3
• Molecular Formula: C₃₉H₃₇NO₈
• Molecular Weight: 647.725

Synonyms:3-benzyloxy-13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-7,8-dihydro-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one

Chemical Property of 3-benzyloxy-13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-7,8-dihydro-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 3-benzyloxy-13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-7,8-dihydro-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one

There total 9 articles about 3-benzyloxy-13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-7,8-dihydro-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-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: 95.0%

7-benzyloxy-3-[2-(3,4-dimethoxy-phenyl)-ethyl]-1-(3-isopropoxy-4-methoxy-phenyl)-8-methoxy-3H-5-oxa-3-aza-cyclopenta[a]naphthalen-4-one (895632-73-2) → 3-benzyloxy-13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-7,8-dihydro-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one (895632-74-3)

Guidance literature:

With boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene; In dichloromethane; at -40 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2006.03.121

Reference yield:

1-[2-(3,4-dimethoxy-phenyl)-ethyl]-3-(3-isopropoxy-4-methoxy-phenyl)-4-trifluoromethanesulfonyloxy-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester (895632-68-5) → 3-benzyloxy-13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-7,8-dihydro-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one (895632-74-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 90 percent / aq. Na₂CO₃ / Pd(PPh₃)4 / tetrahydrofuran / 20 h / Heating

2.1: 93 percent / cc.HCl / methanol / 2 h / Heating

3.1: aq. KOH / ethanol / 3 h / Heating

3.2: 77 percent / p-TsOH / CH₂Cl₂ / 1 h / Heating

4.1: 96 percent / Cu₂O; quinoline / 0.17 h / 220 °C

5.1: 95 percent / phenyliodine bis(trifluoroacetate); BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -40 °C

With quinoline; copper(I) oxide; hydrogenchloride; potassium hydroxide; boron trifluoride diethyl etherate; sodium carbonate; bis-[(trifluoroacetoxy)iodo]benzene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1.1: Suzuki-Miyaura coupling;

DOI:10.1016/j.tetlet.2006.03.121

Reference yield:

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → 3-benzyloxy-13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-7,8-dihydro-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one (895632-74-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 91 percent / NaHCO₃ / acetonitrile / 2.5 h / Heating

2.1: 85 percent / NaH / tetrahydrofuran / 4.5 h / Heating

3.1: 92 percent / pyridine / 2 h / 0 °C

4.1: 80 percent / aq. Na₂CO₃ / Pd(PPh₃)4 / tetrahydrofuran / 5 h / Heating

5.1: 90 percent / aq. Na₂CO₃ / Pd(PPh₃)4 / tetrahydrofuran / 20 h / Heating

6.1: 93 percent / cc.HCl / methanol / 2 h / Heating

7.1: aq. KOH / ethanol / 3 h / Heating

7.2: 77 percent / p-TsOH / CH₂Cl₂ / 1 h / Heating

8.1: 96 percent / Cu₂O; quinoline / 0.17 h / 220 °C

9.1: 95 percent / phenyliodine bis(trifluoroacetate); BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -40 °C

With quinoline; copper(I) oxide; hydrogenchloride; potassium hydroxide; boron trifluoride diethyl etherate; sodium hydride; sodium hydrogencarbonate; sodium carbonate; bis-[(trifluoroacetoxy)iodo]benzene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; acetonitrile; 2.1: Hinsberg-type pyrrole synthesis / 4.1: Suzuki-Miyaura coupling / 5.1: Suzuki-Miyaura coupling;

DOI:10.1016/j.tetlet.2006.03.121

upstream raw materials:

7-benzyloxy-3-[2-(3,4-dimethoxy-phenyl)-ethyl]-1-(3-isopropoxy-4-methoxy-phenyl)-8-methoxy-3H-5-oxa-3-aza-cyclopenta[a]naphthalen-4-one

1-[2-(3,4-dimethoxy-phenyl)-ethyl]-3-(3-isopropoxy-4-methoxy-phenyl)-4-trifluoromethanesulfonyloxy-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester

7-benzyloxy-3-[2-(3,4-dimethoxy-phenyl)-ethyl]-1-(3-isopropoxy-4-methoxy-phenyl)-8-methoxy-4-oxo-3,4-dihydro-5-oxa-3-aza-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester

7-benzyloxy-3-[2-(3,4-dimethoxy-phenyl)-ethyl]-1-(3-isopropoxy-4-methoxy-phenyl)-8-methoxy-4-oxo-3,4-dihydro-5-oxa-3-aza-cyclopenta[a]naphthalene-2-carboxylic acid

Downstream raw materials:

20-benzyl-13-isopropyllamellarin α

3-hydroxy-13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one

14-(3-hydroxy-4-methoxyphenyl)-2,11,12-trimethoxy-6-oxo-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-3-yl 2,2,2-trichloroethyl sulfate

sulfuric acid 13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-6-oxo-6H-5-oxa-6b-aza-dibenzo[a,i]fluoren-3-yl ester 2,2,2-trichloro-ethyl ester

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