57367-54-1

Basic information

• Product Name: 4-Methoxy-4-oxo-3-(triphenylphosphoranylidene)-butanoic acid
• Synonyms: 4-Methoxy-4-oxo-3-(triphenylphosphoranylidene)-butanoic acid
• CAS NO: 57367-54-1
• Molecular Formula: C₂₃H₂₁O₄P
• Molecular Weight: 392.384201
• Mol File: 57367-54-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 574.5±52.0 °C(Predicted)
• Appearance: /
• Density: 1.26±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 4-Methoxy-4-oxo-3-(triphenylphosphoranylidene)-butanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxy-4-oxo-3-(triphenylphosphoranylidene)-butanoic acid(57367-54-1)
• EPA Substance Registry System: 4-Methoxy-4-oxo-3-(triphenylphosphoranylidene)-butanoic acid(57367-54-1)

Safety Data

• Hazardous Substances Data: 57367-54-1(Hazardous Substances Data)

Upstream product

• 603-35-0 triphenylphosphine 
• 67-56-1 methanol 
• 906-65-0 3-(triphenyl-λ-phosphanylidene)dihydrofuran-2,5-dione 

Downstream Products

• 1431641-32-5 C₁₆H₁₈O₇ 
• 945034-38-8 (E)-3-(methoxycarbonyl)-4-(3-aminophenyl)but-3-enoic acid 
• 910575-74-5 2-[1-(3-chloro-4-hydroxy-5-methyl-phenyl)-meth-(Z)-ylidene]-succinic acid 1-methyl ester 
• 688020-92-0 2-[1-(4-amino-3,5-bis-trifluoromethyl-phenyl)-meth-(E)-ylidene]-succinic acid-1-methyl ester 
• 910576-40-8 2-[1-(3-chloro-4-hydroxy-5-trifluoromethyl-phenyl)-meth(Z)-ylidene]-succinic acid 1-methyl ester 
• 96548-65-1 3-(benzo[d][1,3]dioxol-5-ylmethyl)-4-methoxy-4-oxobutanoic acid 
• 150160-53-5 (RS)-5-benzamido-3-(methoxycarbonyl)pentanoic acid 
• 125702-16-1 (E)-3-(methoxycarbonyl)-4-(3-nitrophenyl)but-3-enoic acid 
• 77729-55-6 2-[1-(3,5-Dimethoxy-phenyl)-meth-(E)-ylidene]-succinic acid 1-methyl ester 

Relevant articles and documents

New facile synthesis of furan-2(3H)-ones and 2,3,5-trisubstituted furans via intramolecular Wittig reaction of acid anhydride

A new facile preparation of furan-2(3H)-ones and 2,3,5-trisubstituted furans by a sequential O-acylation/Wittig(/O-acylation)reaction has been developed. The easily accessible 2-(triphenylphosphoranylidene)-succinic acid 1-ester 3 reacted with acid chloride produced furan-2(3H)-ones 4 in good yields in the presence of DMAP via sequential O-acylation and intramolecular Wittig reaction of acid anhydride. Subsequently, the 2,3,5-trisubstituted furans 5 were prepared from furan-2(3H)-ones 4 and diverse aryl chlorides in presence of triethylamine through further O-acylation.

Synthesis of the naphthoquinone core of divergolides (C-D) and model studies for elaboration of the ansabridge

Herein, we describe a facile synthesis of the naphthoquinone fragment of the aromatic core of the novel ansamycins such as hygrocins A-B and the divergolides C-D, starting from the inexpensive 2-hydroxy-3-methylbenzoic acid. We demonstrate the utility of naphthalenic synthon for further elaboration of the ansabridge via C5-C6 bond formation by employing a commercially available sterically demanding organomagnesium reagent as a model ansa chain. Facile conversion of the resulting alcohol to the naphthoquinone fragment of the targets in one pot has also been realized. These model studies set the stage for the completion of total synthesis of the biologically important novel ansamycins.

Synthesis and Analgesic Effects of N--1-oxo-2(R)-benzylpropyl>-L-isoleucyl-L-leucine, a New Potent Inhibitor of Multiple Neurotensin/Neuromedin N Degrading Enzymes

The synthesis of N--1-oxo-2(R)-benzylpropyl>-L-isoleucyl-L-leucine (JMV-390-1, 6a), a multipeptidase inhibitor based on the C-terminal sequence common to neurotensin (NT) and neuromedin N (NN), is described.This compound behaves as a full inhibitor of the major NT/NN degrading enzymes in vitro, e.g. endopeptidase 24.16, endopeptidase 24.15, endopeptidase 24.11, and leucine aminopeptidase (type IV-S), in the nanomolar range (IC50's from 30 to 60 nM).Compound 6a was found to increase endogenous recovery of NT and NN from slices of micehypothalamus depolarized with potassium.In various assays commonly used to select analgesics, e.g. hot-plate test, tail-flick test, acetic acid-induced writhing test, in mice, compound 6a proved to be potent when intracerebroventricularly (icv) injected.The analgesic effects observed were totally (hot-plate test) or largely (tail-flick test) reversed by the opioid antagonist naltrexone.Furthermore, icv injection of compound 6a (10 μg/mouse) was found to significantly potentiate the hypothermic effects of NT or NN.