5-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-pent-3-en-2-one

Base Information

Chemical Name:5-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-pent-3-en-2-one
CAS No.:891718-99-3
Molecular Formula:C₂₃H₂₃NO₃S
Molecular Weight:393.507
Hs Code.:

5-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1<i>H</i>-indol-4-yl]-pent-3-en-2-one

Synonyms:5-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-pent-3-en-2-one

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Chemical Property of 5-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-pent-3-en-2-one

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Technology Process of 5-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-pent-3-en-2-one

There total 12 articles about 5-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-pent-3-en-2-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: 88.0%

: 891718-67-5
[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-acetaldehyde

: 4202-14-6
dimethyl (2-oxopropyl)phosphonate

: 891718-99-3
5-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-pent-3-en-2-one

Guidance literature:: dimethyl (2-oxopropyl)phosphonate; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.5h;

[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-acetaldehyde; In tetrahydrofuran; at 0 - 20 ℃; for 2.5h;
DOI:10.1021/ol060338j

Reference yield:

: 863582-11-0
N-(4-hydroxy-8-methyl-5,8-dihydro-naphthalen-1-yl)-4-methyl-benzenesulfonamide

: 891718-99-3
5-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-pent-3-en-2-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran

2.1: NMO / OsO₄

3.1: NaIO₄; SiO₂

4.1: H₂SO₄ / tetrahydrofuran

5.1: NaBH₄ / tetrahydrofuran; methanol / 1 h / 0 °C

6.1: 5.03 g / NEt₃ / tetrahydrofuran / 1 h / 0 °C

7.1: 90 percent / LiCl; BHT / Pd(PPh₃)2Cl₂ / dimethylformamide / 24 h / 125 °C

8.1: K₂CO₃; MeOH; H₂O / acetone / 2 h / 20 °C

9.1: 2.64 g / IBX / dimethylsulfoxide; tetrahydrofuran / 20 °C

10.1: n-BuLi / tetrahydrofuran / 0.5 h / 0 °C

10.2: 88 percent / tetrahydrofuran / 2.5 h / 0 - 20 °C

With methanol; sodium tetrahydroborate; sodium periodate; n-butyllithium; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methyl-phenol; sulfuric acid; water; silica gel; sodium hydride; potassium carbonate; triethylamine; lithium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; bis-triphenylphosphine-palladium(II) chloride; osmium(VIII) oxide; In tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 4.1: Plieninger indolization / 7.1: Stille coupling / 10.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol060338j

Reference yield:

: 863582-27-8
trifluoro-methanesulfonic acid 5-methyl-4-(toluene-4-sulfonylamino)-5,8-dihydro-naphthalen-1-yl ester

: 891718-99-3
5-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-pent-3-en-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: NMO / OsO₄

2.1: NaIO₄; SiO₂

3.1: H₂SO₄ / tetrahydrofuran

4.1: NaBH₄ / tetrahydrofuran; methanol / 1 h / 0 °C

5.1: 5.03 g / NEt₃ / tetrahydrofuran / 1 h / 0 °C

6.1: 90 percent / LiCl; BHT / Pd(PPh₃)2Cl₂ / dimethylformamide / 24 h / 125 °C

7.1: K₂CO₃; MeOH; H₂O / acetone / 2 h / 20 °C

8.1: 2.64 g / IBX / dimethylsulfoxide; tetrahydrofuran / 20 °C

9.1: n-BuLi / tetrahydrofuran / 0.5 h / 0 °C

9.2: 88 percent / tetrahydrofuran / 2.5 h / 0 - 20 °C

With methanol; sodium tetrahydroborate; sodium periodate; n-butyllithium; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methyl-phenol; sulfuric acid; water; silica gel; potassium carbonate; triethylamine; lithium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; bis-triphenylphosphine-palladium(II) chloride; osmium(VIII) oxide; In tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 3.1: Plieninger indolization / 6.1: Stille coupling / 9.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol060338j