(3aR,9aR)-N-(8-mentholyl)-5-methoxy-3a,4,9,9a-tetrahydrobenz[f]isoindoline

Base Information

• Chemical Name: (3aR,9aR)-N-(8-mentholyl)-5-methoxy-3a,4,9,9a-tetrahydrobenz[f]isoindoline
• CAS No.: 402858-48-4
• Molecular Formula: C₂₃H₃₅NO₂
• Molecular Weight: 357.536

Synonyms:(3aR,9aR)-N-(8-mentholyl)-5-methoxy-3a,4,9,9a-tetrahydrobenz[f]isoindoline

Chemical Property of (3aR,9aR)-N-(8-mentholyl)-5-methoxy-3a,4,9,9a-tetrahydrobenz[f]isoindoline

Chemical Property:

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Technology Process of (3aR,9aR)-N-(8-mentholyl)-5-methoxy-3a,4,9,9a-tetrahydrobenz[f]isoindoline

There total 5 articles about (3aR,9aR)-N-(8-mentholyl)-5-methoxy-3a,4,9,9a-tetrahydrobenz[f]isoindoline 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: 88.0%

7-methoxy-3,13,13-trimethyl-2,3,4,4a,5b,6,11,11a,13,13a-decahydro-1H,5aH-5-oxa-12a-aza-dibenzo[b,h]fluoren-12-one (402858-39-3) → (3aR,9aR)-N-(8-mentholyl)-5-methoxy-3a,4,9,9a-tetrahydrobenz[f]isoindoline (402858-48-4)

Guidance literature:

With aluminium hydride; In tetrahydrofuran; at -10 ℃; for 0.133333h;

DOI:10.1021/jo010746v

Reference yield:

(E)-3-(2-methoxyphenyl)propenal (60125-24-8) → (3aR,9aR)-N-(8-mentholyl)-5-methoxy-3a,4,9,9a-tetrahydrobenz[f]isoindoline (402858-48-4)

Guidance literature:

Multi-step reaction with 4 steps

1: toluene

2: 92 percent / Et₃N / CH₂Cl₂ / 0 °C

3: dimethylformamide / 3.5 h / 153 °C

4: 88 percent / AlH₃ / tetrahydrofuran / 0.13 h / -10 °C

With aluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 3: intramolecular Diels-Alder reaction;

DOI:10.1021/jo010746v

Reference yield:

(-)-aminomenthol (55179-51-6) → (3aR,9aR)-N-(8-mentholyl)-5-methoxy-3a,4,9,9a-tetrahydrobenz[f]isoindoline (402858-48-4)

Guidance literature:

Multi-step reaction with 4 steps

1: toluene

2: 92 percent / Et₃N / CH₂Cl₂ / 0 °C

3: dimethylformamide / 3.5 h / 153 °C

4: 88 percent / AlH₃ / tetrahydrofuran / 0.13 h / -10 °C

With aluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 3: intramolecular Diels-Alder reaction;

DOI:10.1021/jo010746v

upstream raw materials:

7-methoxy-3,13,13-trimethyl-2,3,4,4a,5b,6,11,11a,13,13a-decahydro-1H,5aH-5-oxa-12a-aza-dibenzo[b,h]fluoren-12-one

(E)-3-(2-methoxyphenyl)propenal

(-)-aminomenthol

(2S,7R,9R,10S)-2-[2'-(o-methoxyphenyl)vinyl]-4,4,7-trimethyl-octahydro-2H-1,3-benzoxazine

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