4H-Furo[3,4-b]indole, 4-(phenylsulfonyl)-

Base Information

• Chemical Name: 4H-Furo[3,4-b]indole, 4-(phenylsulfonyl)-
• CAS No.: 89241-37-2
• Molecular Formula: C16H11NO3S
• Molecular Weight: 297.334
• DSSTox Substance ID: DTXSID00440129
• Nikkaji Number: J495.975B
• Wikidata: Q82256348

Synonyms:4-(phenylsulfonyl)-4H-furo[3,4-b]indole;4H-Furo[3,4-b]indole, 4-(phenylsulfonyl)-;89241-37-2;DTXSID00440129;4-(benzenesulfonyl)-4H-furo[3,4-b]indole

Chemical Property of 4H-Furo[3,4-b]indole, 4-(phenylsulfonyl)-

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 297.04596439
• Heavy Atom Count: 21
• Complexity: 480

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)S(=O)(=O)N2C3=CC=CC=C3C4=COC=C42

Technology Process of 4H-Furo[3,4-b]indole, 4-(phenylsulfonyl)-

There total 10 articles about 4H-Furo[3,4-b]indole, 4-(phenylsulfonyl)- 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: 46.0%

1-(phenylsulfonyl)-3-(hydroxymethyl)indole-2-carboxaldehyde (89241-34-9) → 4-(phenylsulfonyl)-4H-furo<3,4-b>indole (89241-37-2)

Guidance literature:

With potassium fluoride; hydroquinone; In acetic acid; at 100 ℃; for 3h;

DOI:10.1016/S0040-4039(00)94105-4

Reference yield:

(1-benzenesulfonyl-3-[1,3]dioxolan-2-yl-1H-indol-2-yl)-methanol → 4-(phenylsulfonyl)-4H-furo<3,4-b>indole (89241-37-2)

Guidance literature:

With boron trifluoride diethyl etherate; hydroquinone; In tetrahydrofuran; at 20 ℃; for 0.25h;

DOI:10.1021/jo010938q

Reference yield:

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) → 4-(phenylsulfonyl)-4H-furo<3,4-b>indole (89241-37-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 96 percent / sodium hydroxide; tetra-n-butylammonium hydrogen sulfate / CH₂Cl₂ / 2 h / 20 °C

2.1: 97 percent / p-toluenesulfonic acid / benzene / 16 h / Heating

3.1: sec-butyllithium / tetrahydrofuran; cyclohexane / 4 h / -70 - 20 °C

3.2: tetrahydrofuran; cyclohexane / 2 h / 20 °C

4.1: 0.31 g / boron trifluoride etherate; hydroquinone / tetrahydrofuran / 0.25 h / 20 °C

With sodium hydroxide; boron trifluoride diethyl etherate; sec.-butyllithium; tetra(n-butyl)ammonium hydrogensulfate; toluene-4-sulfonic acid; hydroquinone; In tetrahydrofuran; dichloromethane; cyclohexane; benzene;

DOI:10.1021/jo010938q

upstream raw materials:

1-(phenylsulfonyl)-3-(hydroxymethyl)indole-2-carboxaldehyde

Indole-3-carboxaldehyde

1-(phenylsulfonyl)indole-3-carbaldehyde

benzenesulfonyl chloride

Downstream raw materials:

5-(phenylsulfonyl)-6,11-epoxy-6,11-dihydro-5H-benzocarbazole

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