Acolbifene

Base Information

• Chemical Name: Acolbifene
• CAS No.: 182167-02-8
• Molecular Formula: C29H32ClNO4
• Molecular Weight: 457.569
• UNII: 815LJ9X0D1
• DSSTox Substance ID: DTXSID501318411
• Nikkaji Number: J883.237D
• Wikipedia: Acolbifene
• Wikidata: Q15633957
• NCI Thesaurus Code: C64183
• ChEMBL ID: CHEMBL68055
• Mol file: 182167-02-8.mol

Synonyms:Acolbifene;bis(4-piperidinophenol)diimidonaphthalene-1,4,5,8-tetracarboxylic acid dibenzosulfoethylate;bis(p-piperidinophenol)diimidonaphthalene-1,4,5,8-tetracarboxylic acid dibenzosulfoethylate;EM 652;EM-652;IEM 652;ritebronii;ritebronium;ritetronium;ritetronium dibenzenesulfonate;ritetroniy;SCH 57068;SCH57068

Chemical Property of Acolbifene

Chemical Property:

• Boiling Point: 651.5°Cat760mmHg
• PKA: 9.70±0.40(Predicted)
• Flash Point: 347.8°C
• PSA: 62.16000
• Density: g/cm³
• LogP: 6.76680
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 457.22530847
• Heavy Atom Count: 34
• Complexity: 674

Purity/Quality:

97% ^*data from raw suppliers

Acolbifene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(OC2=C1C=CC(=C2)O)C3=CC=C(C=C3)OCCN4CCCCC4)C5=CC=C(C=C5)O
• Isomeric SMILES: CC1=C([C@@H](OC2=C1C=CC(=C2)O)C3=CC=C(C=C3)OCCN4CCCCC4)C5=CC=C(C=C5)O
• Uses: Prevention or treatment of breast and uterine proliferation or cancer.

Technology Process of Acolbifene

There total 8 articles about Acolbifene 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:

(2S)-7-hydroxy-3-(4'-hydroxyphenyl)-4-methyl-2-((4''-[2'''-piperidino]ethoxy)phenyl)-2H-1-benzopyran (1S)-10-camphorsulphonic acid salt (182167-59-5) → Acolbifene (182167-02-8)

Guidance literature:

With sodium carbonate; In water; ethyl acetate; N,N-dimethyl-formamide; for 4h;

Reference yield:

2,4,4'-trihydroxy deoxybenzoin (17720-60-4,423150-69-0) → Acolbifene (182167-02-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 69 percent / TsOH / 2.5 h / 0 °C

2: 1.) piperidine, 2.) Cs₂CO₃, H₂O / 1.) benzene, reflux, 60 h, 2.) acetone, reflux, 19 h

3: tetrahydrofuran / 3 h / -78 - 20 °C

4: aq. AcOH / 0.5 h / 90 °C

With piperidine; water; caesium carbonate; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran;

DOI:10.1021/jm970095o

Reference yield:

4-hydroxyphenylacetate (156-38-7) → Acolbifene (182167-02-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / BF₃*Et₂O / 1 h / 100 °C

2: 69 percent / TsOH / 2.5 h / 0 °C

3: 1.) piperidine, 2.) Cs₂CO₃, H₂O / 1.) benzene, reflux, 60 h, 2.) acetone, reflux, 19 h

4: tetrahydrofuran / 3 h / -78 - 20 °C

5: aq. AcOH / 0.5 h / 90 °C

With piperidine; boron trifluoride diethyl etherate; water; caesium carbonate; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran;

DOI:10.1021/jm970095o

upstream raw materials:

2-[4-[2-(1-piperidino)ethoxy]phenyl]-3-(4-hydroxyphenyl)-4-methyl-7-hydroxy-2H-1-benzopyran

2,4,4'-trihydroxy deoxybenzoin

4-hydroxyphenylacetate

1-(2-hydroxy-4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethanone

Downstream raw materials:

(S)-(+)-7-hydroxy-3-(4'-hydroxyphenyl)-4-methyl-2-(4''-(2'''-piperidinoethoxy)phenyl)-2H-1-benzopyran hydrochloride

EM-800