Panomifene

Base Information

• Chemical Name: Panomifene
• CAS No.: 77599-17-8
• Molecular Formula: C₂₅H₂₄F₃NO₂
• Molecular Weight: 427.466
• UNII: GCW5E728OC
• DSSTox Substance ID: DTXSID401032965
• Nikkaji Number: J2.148.593D
• Wikipedia: Panomifene
• Wikidata: Q27279037
• NCI Thesaurus Code: C66304
• ChEMBL ID: CHEMBL2105273
• Mol file: 77599-17-8.mol

Synonyms:1,2-diphenyl-1(4-((2-hydroxyethylamino)ethoxy)phenyl)-3,3,3-trifluoro-1-propene;EGIS 5650;EGIS-5650;GYKI 13504;GYKI-13504;panomifene

Chemical Property of Panomifene

Chemical Property:

• Vapor Pressure: 5.79E-13mmHg at 25°C
• Boiling Point: 550.7°C at 760 mmHg
• Flash Point: 286.9°C
• PSA: 41.49000
• Density: 1.203g/cm³
• LogP: 5.55960
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 427.17591349
• Heavy Atom Count: 31
• Complexity: 544

Purity/Quality:

95% ^*data from raw suppliers

Panomifene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)C(F)(F)F)C3=CC=C(C=C3)OCCNCCO
• Isomeric SMILES: C1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\C(F)(F)F)/C3=CC=C(C=C3)OCCNCCO
• Uses: Panomifene is an analogue to tamoxifen (T006000), an antiestrogen currently used as a therapeutic agent against breast cancer, and there are some similar routes in their metabolism.

Technology Process of Panomifene

There total 16 articles about Panomifene 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: 83.0%

ethanolamine (141-43-5) + (E)-3,3,3-trifluoro-1-[4-(2-chloroethoxy)phenyl]-1,2-diphenylpropene (179031-96-0) → (E)-3,3,3-trifluoro-1-{4-[2-(2-hydroxyethylamino)ethoxy]phenyl}-1,2-diphenylpropene (77599-17-8)

Guidance literature:

In 2-methoxy-ethanol; for 1h; Heating;

DOI:10.1016/0040-4020(96)00763-6

Reference yield:

4,4,5,5-Tetramethyl-2-[(E)-3,3,3-trifluoro-1-(4-methoxy-phenyl)-2-phenyl-propenyl]-[1,3,2]dioxaborolane → (E)-3,3,3-trifluoro-1-{4-[2-(2-hydroxyethylamino)ethoxy]phenyl}-1,2-diphenylpropene (77599-17-8)

Guidance literature:

Multi-step reaction with 4 steps

1: Pd(P-t-Bu₃P)2; Cs₂CO₃ / dioxane; H₂O / 50 °C

2: 78 percent / NaSEt / dimethylformamide / 10 h / 150 °C

3: K₂CO₃ / acetonitrile / 12 h / Heating

4: 2-methoxy-ethanol / 2 h / Heating

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate; caesium carbonate; sodium thioethylate; In 1,4-dioxane; 2-methoxy-ethanol; water; N,N-dimethyl-formamide; acetonitrile; 1: Suzuki-Miyaura coupling reaction;

DOI:10.1002/anie.200353032

Reference yield:

3,3,3-trifluoro-1-phenylpropyne (772-62-3) → (E)-3,3,3-trifluoro-1-{4-[2-(2-hydroxyethylamino)ethoxy]phenyl}-1,2-diphenylpropene (77599-17-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: copper(I) cyanide / tetrahydrofuran / -45 - -5 °C

1.2: 51 percent / iodine / tetrahydrofuran / 1 h

2.1: boron tribromide / CH₂Cl₂ / 1 h / 20 °C

3.1: 74 mg / NaH / dimethylformamide / 0 - 80 °C

4.1: 100 percent / sodium carbonate / Pd(PPh₃)4 / benzene; H₂O; ethanol / 12 h / Heating

5.1: 83 percent / 10 h / Heating

With copper(l) cyanide; boron tribromide; sodium hydride; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene; 4.1: Suzuki-Miyaura cross-coupling;

DOI:10.1016/j.tet.2005.07.022

upstream raw materials:

ethanolamine

(E)-3,3,3-trifluoro-1-[4-(2-chloroethoxy)phenyl]-1,2-diphenylpropene

3,3,3-trifluoro-1-phenylpropyne

4-methoxyphenyl magnesium bromide

Refernces

Highly regio- and stereo-selective carbometallation reaction of fluorine-containing internal acetylenes with organocopper reagents

10.1016/j.tet.2005.07.022

The study focuses on the carbometallation reactions of fluorine-containing internal acetylenes with various organocopper reagents derived from organolithium, Grignard, and organozinc reagents. The main objective was to investigate the regio- and stereo-selectivity of these reactions, which are crucial for the synthesis of fluoroalkylated molecules, particularly alkenes with fluoroalkyl groups that are found in biologically active compounds. The reactions proceeded smoothly, yielding vinylcopper intermediates that could then react with electrophiles to form trisubstituted alkenes in high to excellent yields. The study also successfully applied these reactions in the total synthesis of the anti-estrogen drug, panomifene, demonstrating the synthetic utility of the developed methods. Chemicals used in the study included fluoroalkylated internal alkynes, organocopper reagents, and various electrophiles for cross-coupling reactions, serving the purpose of exploring novel synthetic approaches for the preparation of fluoroalkylated molecules with potential pharmaceutical applications.