2-{2-[(1R,2S,3R)-3-Benzyl-2-((Z)-propenyl)-cyclopentyl]-allyl}-benzo[de]isoquinoline-1,3-dione

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Chemical Name:2-{2-[(1R,2S,3R)-3-Benzyl-2-((Z)-propenyl)-cyclopentyl]-allyl}-benzo[de]isoquinoline-1,3-dione
CAS No.:131140-40-4
Molecular Formula:C₃₀H₂₉NO₂
Molecular Weight:435.566
Hs Code.:

Synonyms:2-{2-[(1R,2S,3R)-3-Benzyl-2-((Z)-propenyl)-cyclopentyl]-allyl}-benzo[de]isoquinoline-1,3-dione

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Chemical Property of 2-{2-[(1R,2S,3R)-3-Benzyl-2-((Z)-propenyl)-cyclopentyl]-allyl}-benzo[de]isoquinoline-1,3-dione

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Technology Process of 2-{2-[(1R,2S,3R)-3-Benzyl-2-((Z)-propenyl)-cyclopentyl]-allyl}-benzo[de]isoquinoline-1,3-dione

There total 11 articles about 2-{2-[(1R,2S,3R)-3-Benzyl-2-((Z)-propenyl)-cyclopentyl]-allyl}-benzo[de]isoquinoline-1,3-dione 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: 79.0%

: 81-83-4
1,8-Naphthalimide

: 131140-39-1
2-[(1S,2R,3S)-3-Benzyl-2-((Z)-propenyl)-cyclopentyl]-prop-2-en-1-ol

: 131140-40-4
2-{2-[(1R,2S,3R)-3-Benzyl-2-((Z)-propenyl)-cyclopentyl]-allyl}-benzo[de]isoquinoline-1,3-dione

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; for 2h;
DOI:10.1016/S0040-4020(01)87749-8

Reference yield:

: 542-28-9,26354-94-9
3,4,5,6-tetrahydro-2H-pyran-2-one

: 131140-40-4
2-{2-[(1R,2S,3R)-3-Benzyl-2-((Z)-propenyl)-cyclopentyl]-allyl}-benzo[de]isoquinoline-1,3-dione

Guidance literature:: Multi-step reaction with 10 steps

1: 59 percent / HMPA, diisopropylamine, n-butyllithium / tetrahydrofuran / 5 h / -78 - 20 °C

2: 99 percent / DIBAL-H / tetrahydrofuran / 1 h / -78 °C

3: 70 percent / imidazole / dimethylformamide / 0.67 h / 50 °C

4: 1.)HMPA, n-butyllithium / 1.)THF, -78 deg C, 5 min., 2.)THF, -78 deg C -> 25 deg C, 12 h

5: Dowex 50W-8X / methanol / 12 h

6: 96 percent / 1.)oxalyl chloride, DMSO, 2.)triethylamine / CH₂Cl₂ / 1.)-55 deg C, 15 min., 2.)-55 deg C -> 25 deg C

7: 1.)n-butyllithium / 1.)THF, 0 deg C, 2.)THF, a.)0 deg C, 30 min., b.)25 deg C, 1.5 h

8: active iron catalyst / benzene / 7 h

9: 80 percent / DIBAL-H / tetrahydrofuran / 2 h / 0 - 20 °C

10: 79 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 2 h / 0 - 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; Dowex 50W-8X; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine; diethylazodicarboxylate; iron catalyst; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(01)87749-8

Reference yield:

: 32821-74-2
(±)-3-benzyltetrahydro-2H-pyran-2-one

: 131140-40-4
2-{2-[(1R,2S,3R)-3-Benzyl-2-((Z)-propenyl)-cyclopentyl]-allyl}-benzo[de]isoquinoline-1,3-dione

Guidance literature:: Multi-step reaction with 9 steps

1: 99 percent / DIBAL-H / tetrahydrofuran / 1 h / -78 °C

2: 70 percent / imidazole / dimethylformamide / 0.67 h / 50 °C

3: 1.)HMPA, n-butyllithium / 1.)THF, -78 deg C, 5 min., 2.)THF, -78 deg C -> 25 deg C, 12 h

4: Dowex 50W-8X / methanol / 12 h

5: 96 percent / 1.)oxalyl chloride, DMSO, 2.)triethylamine / CH₂Cl₂ / 1.)-55 deg C, 15 min., 2.)-55 deg C -> 25 deg C

6: 1.)n-butyllithium / 1.)THF, 0 deg C, 2.)THF, a.)0 deg C, 30 min., b.)25 deg C, 1.5 h

7: active iron catalyst / benzene / 7 h

8: 80 percent / DIBAL-H / tetrahydrofuran / 2 h / 0 - 20 °C

9: 79 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 2 h / 0 - 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; Dowex 50W-8X; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; iron catalyst; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(01)87749-8