2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol

2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol Basic information
Product Name:2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol
Synonyms:2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol;2-[4-[(1Z)-4-chloro-1,2-diphenyl-1-buten-1-yl]phenoxy]-ethanol;2-(p-((Z)-4-Chloro-1,2-diphenyl-1-butenyl)phenoxy)ethanol;Ccris 9205;Fc-1271a;Ospemifene;Unii-B0p231ilbk;2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]ethanol
CAS:128607-22-7
MF:C24H23ClO2
MW:378.89
EINECS:664-452-6
Product Categories:Inhibitors
Mol File:128607-22-7.mol
2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol Structure
2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol Chemical Properties
Boiling point 544.6±50.0 °C(Predicted)
density 1.166±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,2-8°C
solubility DMSO: soluble20mg/mL, clear
pka14.26±0.10(Predicted)
form powder
color white to beige
InChIKeyLUMKNAVTFCDUIE-VHXPQNKSSA-N
CAS DataBase Reference128607-22-7
Safety Information
Hazard Codes N
Risk Statements 50/53
Safety Statements 60-61
RIDADR UN 3077 9 / PGIII
WGK Germany 3
HS Code 2909.49.1500
Hazardous Substances Data128607-22-7(Hazardous Substances Data)
MSDS Information
2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol Usage And Synthesis
DescriptionIn February 2013, the US FDA approved ospemifene (also referred to as FC1271a), for the treatment ofmoderate to severe dyspareunia, a symptom of vulvar and vaginal atrophy (VVA), due tomenopause. It is estimated that there are 150 million postmenopausal women worldwide with 40–70% suffering from VVA. Ospemifene is a selective estrogen receptor (ER) modulator (SERM) and the first nonhormonal, nonestrogen for the treatment of moderate to severe dyspareunia in women with menopausal VVA. It binds to ERα (IC50~800 nM) and ERβ (IC50~1600 nM) with tissue-specific estrogenic agonist/antagonist effects. Treatment with ospemifene increases the thickness of the vaginal tissue thereby decreasing fragility of the tissue and reducing potential for pain during sexual intercourse.
OriginatorTess Diagnostics and Pharmaceuticals/Hormos Medical/QuatRx (Finland)
UsesTreatment of vaginal atrophy, osteoporosis, and vasomotor symptoms.
DefinitionChEBI: An organochlorine compound that is a selective estrogen receptor modulator; used for treatment of dyspareunia.
Brand nameOsphena
Clinical UseOspemifene is a SERM that is currently in Phase II/III clinical trials for the treatment of postmenopausal osteoporosis and urogenital atrophy. It is a known metabolite of toremifene, a triphenylethylene derivative used to treat breast cancer.Ospemifene has been shown to have beneficial effects on the bone without significant estrogen-related side effects. The beneficial effect observed on bone stems from this agent's ability to increase osteoblast proliferation and, as a result, to enhance bone mineralization as well as bone formation. Unlike tamoxifen, ospemifene does not induce osteocyte apoptosis.
SynthesisThe drug can be synthesized succinctly in two steps. First, alkylation of commercially available 4-hydroxybenzophenone (130) with ethylene carbonate and catalytic sodium iodide in refluxing toluene provided benzophenone 131 in 94% yield. This was followed by a McMurry coupling involving benzophenone 131 with chloropropiophenone 132 in the presence of zinc powder and titanium tetrachloride in 2-methyltetrahydrofuran. This reaction gave rise to a mixture of triphenylethylenes directly as a 5.5:1 ratio of Z to E isomers which could be separated by crystallization in aqueous methanol to give a mixture of olefins, 98% of which was comprised of the desired Z-isomer corresponding to ospemifene (XVII). The product purity was further improved by recrystallization to give 99.9% of the Z-isomer in 46% yield from 131. Thus, ospemifene was synthesized in two steps and 43% overall yield.

Synthesis_128607-22-7

2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol Preparation Products And Raw materials
Fulvestrant Toremifene citrate Raloxifene hydrochloride

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