4H-Indol-4-one, 1,5,6,7-tetrahydro-2,6,6-trimethyl-1-(4-methylphenyl)-

Base Information

• Chemical Name: 4H-Indol-4-one, 1,5,6,7-tetrahydro-2,6,6-trimethyl-1-(4-methylphenyl)-
• CAS No.: 163083-04-3
• Molecular Formula: C18H21NO
• Molecular Weight: 267.371
• DSSTox Substance ID: DTXSID60414588
• Nikkaji Number: J716.133F
• Wikidata: Q82223517
• Mol file: 163083-04-3.mol

Synonyms:163083-04-3;2,6,6-Trimethyl-1-(p-tolyl)-6,7-dihydro-1H-indol-4(5H)-one;4H-Indol-4-one, 1,5,6,7-tetrahydro-2,6,6-trimethyl-1-(4-methylphenyl)-;DTXSID60414588;AKOS002776772

Chemical Property of 4H-Indol-4-one, 1,5,6,7-tetrahydro-2,6,6-trimethyl-1-(4-methylphenyl)-

Chemical Property:

• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 267.162314293
• Heavy Atom Count: 20
• Complexity: 381

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)N2C(=CC3=C2CC(CC3=O)(C)C)C

Technology Process of 4H-Indol-4-one, 1,5,6,7-tetrahydro-2,6,6-trimethyl-1-(4-methylphenyl)-

There total 2 articles about 4H-Indol-4-one, 1,5,6,7-tetrahydro-2,6,6-trimethyl-1-(4-methylphenyl)- 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: 80.0%

3-hydroxy-5,5-dimethyl-2-(2-oxopropyl)-2-cyclohex-1-one (13148-87-3) + p-toluidine (106-49-0,12221-03-3) → 1-(4-methylphenyl)-2,6,6-trimethyl-4,5,6,7-tetrahydroindol-4-one (163083-04-3)

Guidance literature:

With acetic acid; for 12h; Heating;

DOI:10.1016/j.bmc.2006.02.012

Reference yield:

dimedone (126-81-8) → 1-(4-methylphenyl)-2,6,6-trimethyl-4,5,6,7-tetrahydroindol-4-one (163083-04-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / potassium carbonate / CHCl₃ / 48 h / 20 °C

2: 80 percent / acetic acid / 12 h / Heating

With potassium carbonate; acetic acid; In chloroform; 2: Paal-Knorr reaction;

DOI:10.1016/j.bmc.2006.02.012

Reference yield: 96.0%

1-(4-methylphenyl)-2,6,6-trimethyl-4,5,6,7-tetrahydroindol-4-one (163083-04-3) → 1-(4-methylphenyl)-2,6,6-trimethyl-4,5,6,7-tetrahydroindol-4-one oxime (176314-14-0)

Guidance literature:

With sodium hydroxide; hydroxylamine hydrochloride; In ethanol; water; for 2h; Heating;

DOI:10.1016/j.bmc.2006.02.012

upstream raw materials:

3-hydroxy-5,5-dimethyl-2-(2-oxopropyl)-2-cyclohex-1-one

p-toluidine

dimedone

Downstream raw materials:

1-(4-methylphenyl)-2,6,6-trimethyl-4,5,6,7-tetrahydroindol-4-one oxime

6H-1-(4-methylphenyl)-2,7,7-trimethyl-4,5,7,8-tetrahydropyrrolo[3,2-c]azepin-4-one

Refernces

• 1、 Martínez, Roberto,ávila, J. Gustavo,Ramírez, Ma. Teresa,Pérez, Araceli,Martínez, ángeles. "Tetrahydropyrrolo[3,2-c]azepin-4-ones as a new class of cytotoxic compounds". . p. 4007 - 4016. Retrieved 2007/10/03.