Biphenylindanone A

Base Information

• Chemical Name: Biphenylindanone A
• CAS No.: 866823-73-6
• Molecular Formula: C₃₀H₃₀O₄
• Molecular Weight: 454.566
• DSSTox Substance ID: DTXSID90432098
• Wikipedia: Biphenylindanone_A
• Wikidata: Q4915436
• Pharos Ligand ID: 9PVMFDV7CRQS
• Metabolomics Workbench ID: 143804
• ChEMBL ID: CHEMBL593013
• Mol file: 866823-73-6.mol

Synonyms:3'-(((2-cyclopentyl-6,7-dimethyl-1-oxo-2,3-dihydro-1H-inden-5-yl)oxy)methyl)biphenyl-4-carboxylic acid;BINA cpd;biphenyl-indanone A

Chemical Property of Biphenylindanone A

Chemical Property:

• Melting Point: 238-241℃
• PSA: 63.60000
• Density: 1.220
• LogP: 6.79280
• Storage Temp.: Desiccate at RT
• Solubility.: DMSO: ≥18mg/mL
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 454.21440943
• Heavy Atom Count: 34
• Complexity: 719

Purity/Quality:

97% ^*data from raw suppliers

Biphenyl-indanone A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C2CC(C(=O)C2=C1C)C3CCCC3)OCC4=CC(=CC=C4)C5=CC=C(C=C5)C(=O)O
• Description: The metabotropic glutamate receptor 2 (mGluR2) is a Gi/o-coupled receptor which is expressed on presynaptic nerve terminals and modulates the release of neurotransmitters like glutamate and GABA. Biphenylindanone A (BINA) is a positive allosteric modulator of mGluR2, stimulating the human and rat receptors with EC50 values of 33.2 and 96 nM, respectively. It has no effect on glutamate-induced activation of other mGluR types. BINA can be used on cells, tissues, or animals. Because of its selectivity for mGluR2, robust in vivo activity, and brain penetrance, BINA can be used to elucidate the role of mGluR2 in such diverse processes as psychosis, schizophrenia, and drug addiction.
• Uses: Biphenylindanone A is an orally active metabotropic glutamate subtype 2 receptor positive allosteric modulator.

Technology Process of Biphenylindanone A

There total 14 articles about Biphenylindanone A 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: 63.0%

ethyl 3'-(((2-cyclopentyl-6.7-dimethyl-1-oxo-2,3-dihydro-1H-inden-5-yl)oxy)methyl)biphenyl-4-carboxylate (906483-43-0) → Biphenylindanone A (866823-73-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 60 ℃; for 2h;

DOI:10.1124/jpet.106.102046

Reference yield:

2-cyclopentyl-5-{[3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzyl]oxy}-6,7-dimethylindan-1-one (866823-97-4) → Biphenylindanone A (866823-73-6)

Guidance literature:

2-cyclopentyl-5-{[3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzyl]oxy}-6,7-dimethylindan-1-one; 4-bromobenzoic acid ester; With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In methanol; toluene; at 80 ℃; for 18h;

With lithium hydroxide; In tetrahydrofuran; at 50 ℃; for 48h;

DOI:10.1016/j.bmcl.2005.06.062

Reference yield:

2-cyclopentyl-5-hydroxy-6,7-dimethyl-indan-1-one (41715-84-8) → Biphenylindanone A (866823-73-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / potassium carbonate / dimethylformamide / 14 h / 75 °C

2: 63 percent / sodium hydroxide / tetrahydrofuran; methanol / 2 h / 60 °C

With sodium hydroxide; potassium carbonate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1124/jpet.106.102046

upstream raw materials:

2-cyclopentyl-5-{[3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzyl]oxy}-6,7-dimethylindan-1-one

ethyl 3'-(((2-cyclopentyl-6.7-dimethyl-1-oxo-2,3-dihydro-1H-inden-5-yl)oxy)methyl)biphenyl-4-carboxylate

meta-bromotoluene

2-cyclopentylacetyl chloride