6-Methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one

Base Information

• Chemical Name: 6-Methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one
• CAS No.: 856925-72-9
• Molecular Formula: C18H16 N2 O
• Molecular Weight: 276.33200
• Nikkaji Number: J2.184.495K
• Mol file: 856925-72-9.mol

Synonyms:6-Methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one;starbld0006768;SCHEMBL25858393

Chemical Property of 6-Methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one

Chemical Property:

• Melting Point: 126-128°C
• PSA: 36.10000
• LogP: 3.59570
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 276.126263138
• Heavy Atom Count: 21
• Complexity: 464

Purity/Quality:

98%Min ^*data from raw suppliers

Deoxyblebbistatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)NC3=C(C2=O)CCN3C4=CC=CC=C4

Technology Process of 6-Methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one

There total 7 articles about 6-Methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-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: 98.0%

methyl 5-methyl-2-((1-phenylpyrrolidin-2-ylidene)amino)benzoate → 6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (856925-72-9)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃; for 1h; Inert atmosphere;

DOI:10.1039/c7ob00006e

Reference yield: 90.0%

methyl 5-methyl-2-(1-phenylpyrrolidin-2-ylideneamino)benzoate → 6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (856925-72-9)

Guidance literature:

With lithium hexamethyldisilazane; at -78 - 0 ℃; for 3h;

DOI:10.1002/ejoc.200500103

Reference yield: 43.0%

(3aS)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (1177356-70-5,674289-55-5,856925-71-8) → 6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (856925-72-9)

Guidance literature:

In water; acetonitrile; at 20 ℃; for 2h; Wavelength; Irradiation;

DOI:10.1021/jacs.8b10235

upstream raw materials:

1-phenylpyrrolidin-2-one

2-amino-5-methylbenzoic acid methyl ester

2-Amino-5-methylbenzoic acid

iodobenzene

Downstream raw materials:

(3aR)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one

(3aS)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one

(±)-1,2,3,3a-tetrahydro-3a-hydroxy-6-methyl-1-phenyl-4Hpyrrolo[2,3-b]quinolin-4-one

Refernces

• 1、 Verhasselt, Sigrid,Roman, Bart I.,De Wever, Olivier,Van Hecke, Kristof,Van Deun, Rik,Bracke, Marc E.,Stevens, Christian V.. "Discovery of (S)-3′-hydroxyblebbistatin and (S)-3′-aminoblebbistatin: polar myosin II inhibitors with superior research tool properties". . p. 2104 - 2118. Retrieved 2017/03/11.
• 2、 Lucas-Lopez, Cristina,Patterson, Stephen,Blum, Till,Straight, Aaron F.,Toth, Judit,Slawin, Alexandra M. Z.,Mitchison, Timothy J.,Sellers, James R.,Westwood, Nicholas J.. "Absolute stereochemical assignment and fluorescence tuning of the small molecule tool, (-)-blebbistatin". . p. 1736 - 1740. Retrieved 2007/10/03.