91817-43-5

Basic information

• Product Name: 3-Cyclohexene-1-carboxylic acid, 4-methoxy-2-oxo-, methyl ester
• CAS NO: 91817-43-5
• Molecular Formula: C9H12O4
• Molecular Weight: 184.192
• Mol File: 91817-43-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-Cyclohexene-1-carboxylic acid, 4-methoxy-2-oxo-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclohexene-1-carboxylic acid, 4-methoxy-2-oxo-, methyl ester(91817-43-5)
• EPA Substance Registry System: 3-Cyclohexene-1-carboxylic acid, 4-methoxy-2-oxo-, methyl ester(91817-43-5)

Safety Data

• Hazardous Substances Data: 91817-43-5(Hazardous Substances Data)

Upstream product

• 16807-60-6 3-methoxycyclohex-2-en-1-one 
• 17640-15-2 methyl cyanoformate 
• 504-02-9 1,3-cylohexanedione 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 1196989-55-5 methyl (+/-)-1-benzyl-4-methoxy-2-oxo-3-cyclohexene-1-carboxylate 
• 1196989-47-5 methyl (+/-)-4-methoxy-1-(2-nitrobenzyl)-2-oxo-3-cyclohexene-1-carboxylate 
• 1193346-10-9 C₁₂H₁₆O₄ 

Relevant articles and documents

Total syntheses of (±)-platencin and (-)-platencin

The secondary metabolites platensimycin and platencin, isolated from the bacterial strain Streptomyces platensis, represent a novel class of natural products exhibiting unique and potent antibacterial activity. Platencin, though structurally similar to platensimycin, has been found to operate through a slightly different mechanism of action involving the dual inhibition of lipid elongation enzymes FabF and FabH. Both natural products exhibit strong, broad-spectrum, Gram-positive antibacterial activity to key antibiotic resistant strains, including methicillin-resistant Staphylococcus aureus, vancomycin-intermediate S. aureus, and vancomycin-resistant Enterococcus faecium. Described herein are our synthetic efforts toward platencin, culminating in both racemic and asymmetric preparation of the natural product. The syntheses demonstrate the power of the cobalt-catalyzed asymmetric Diels-Alder reaction and the one-pot reductive rearrangement of [3.2.1] bicyclic ketones to [2.2.2] bicyclic olefins.

Tricarbonylcyclohexadienyliron Complexes as Aryl Equivalents: A Formal Synthesis of (+/-)-O-Methyljoubertiamine

The use of tricarbonyl(4-methoxycyclohexadienyl)iron hexafluorophosphate 1b as a synthetic equivalent of the p-anisyl cation for a formal synthesis of (+/-)-O-methyljoubertiamine is described.