4-(3-butenyl)-5-methyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole

Base Information

• Chemical Name: 4-(3-butenyl)-5-methyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole
• CAS No.: 157331-62-9
• Molecular Formula: C₂₂H₂₃NO₂S
• Molecular Weight: 365.496
• Mol file: 157331-62-9.mol

Synonyms:4-(3-butenyl)-5-methyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole

Chemical Property of 4-(3-butenyl)-5-methyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(3-butenyl)-5-methyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole

There total 7 articles about 4-(3-butenyl)-5-methyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole 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: 90.0%

5-methyl-1-(phenylsulfonyl)-4-<(phenylsulfonyl)methyl>-1,6,7,8-tetrahydrocyclopentindole (157331-54-9) + allyl-trimethyl-silane (762-72-1) → 4-(3-butenyl)-5-methyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole (157331-62-9)

Guidance literature:

With ethylaluminum dichloride; In hexane; dichloromethane; at -20 ℃; for 0.5h;

DOI:10.1248/cpb.42.846

Reference yield:

1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (88075-95-0) → 4-(3-butenyl)-5-methyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole (157331-62-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) lithium diisopropylamide / 1.) THF, -82 deg C to -69 deg C, 45 min, 2.) THF, -69 deg C to -59 deg C, 1 h

2: 84 percent / MnO₂ / CH₂Cl₂ / 2 h / Heating

3: 70 percent / LiCl, H₂O / hexamethylphosphoric acid triamide / 14 h / 130 - 135 °C

4: 1.) n-BuLi / 1.) THF, hexane a) -80 deg C to -72 deg C, 20 min, b) -20 deg C, 10 min, 2.) THF, hexane, -80 deg C to -75 deg C, 20 min

5: 72 percent / NaIO₄, OsO₄ / tetrahydrofuran; H₂O / 14 h / Ambient temperature

6: 93 percent / PhCH₂SH, p-TsOH*H₂O / benzene / 2 h / Heating

7: 90 percent / EtAlCl₂ / hexane; CH₂Cl₂ / 0.5 h / -20 °C

With manganese(IV) oxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; water; ethylaluminum dichloride; toluene-4-sulfonic acid; phenylmethanethiol; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; benzene;

DOI:10.1248/cpb.42.846

Reference yield:

3-<(2ξ)-2-<(ξ)-2-methylenecyclopentyl>-1-oxo>propyl-1-(phenylsulfonyl)-1H-pyrrole → 4-(3-butenyl)-5-methyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole (157331-62-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi / 1.) THF, hexane a) -80 deg C to -72 deg C, 20 min, b) -20 deg C, 10 min, 2.) THF, hexane, -80 deg C to -75 deg C, 20 min

2: 72 percent / NaIO₄, OsO₄ / tetrahydrofuran; H₂O / 14 h / Ambient temperature

3: 93 percent / PhCH₂SH, p-TsOH*H₂O / benzene / 2 h / Heating

4: 90 percent / EtAlCl₂ / hexane; CH₂Cl₂ / 0.5 h / -20 °C

With sodium periodate; osmium(VIII) oxide; n-butyllithium; ethylaluminum dichloride; toluene-4-sulfonic acid; phenylmethanethiol; In tetrahydrofuran; hexane; dichloromethane; water; benzene;

DOI:10.1248/cpb.42.846

upstream raw materials:

5-methyl-1-(phenylsulfonyl)-4-<(phenylsulfonyl)methyl>-1,6,7,8-tetrahydrocyclopentindole

allyl-trimethyl-silane

1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde

ethyl (αξ)-α-methyl-α-<(ξ)-2-methylenecyclopentyl>-β-oxo-1-(phenylsulfonyl)-1H-pyrrole-3-propanoate

Downstream raw materials:

4-<(E)-1-butenyl>-5-methyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole