72284-17-4

Basic information

• Product Name: 2-Nonenoic acid, ethyl ester, (Z)-
• CAS NO: 72284-17-4
• Molecular Formula: C11H20O2
• Molecular Weight: 184.279
• Mol File: 72284-17-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-Nonenoic acid, ethyl ester, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nonenoic acid, ethyl ester, (Z)-(72284-17-4)
• EPA Substance Registry System: 2-Nonenoic acid, ethyl ester, (Z)-(72284-17-4)

Safety Data

• Hazardous Substances Data: 72284-17-4(Hazardous Substances Data)

Upstream product

• 111-71-7 heptanal 
• 623-51-8 ethyl 2-sulfanylacetate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 3761-92-0 n-hexylmagnesium bromide 
• 623-47-2 propynoic acid ethyl ester 
• 1071-46-1 hydrogen ethyl malonate 
• 311-46-6 ethyl 2-(dimethoxyphosphoryl)acetate 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 52790-15-5 O-Ethyl S-ethoxycarbonylmethyl thiocarbonate 

Relevant articles and documents

A highly stereoselective TMSOTf-mediated catalytic carbocupration of alkynoates

(Chemical Equation Presented) The TMSOTf-mediated catalytic carbocupration of ynoates has been investigated. It has been shown that catalyst loadings as low as 5 mol % readily allow for high yields and diastereosetectivities for a series of aromatic Grignard reagents. In addition, we have been successful in vicinally functionalizing 1a via initial TMSOTf-mediated catalytic carbocupration followed by a secondary electrophilic capture of the TMS allenoate intermediate.

Stereocontrol of the Horner-Wadsworth-Emmons Reaction: Application to the Synthesis of HIV-1 Protease Inhibitors

A systematic study on the Horner-Wadsworth-Emmons (HWE) reaction has shown that ethyl diphenylphosphonoacetate and methyl diphenylphosphonoacetate give a high excess of (Z)-alkenes. These reaction conditions were then used to prepare (Z)-ethyl-5-phenylpent-2-enoate, the corresponding (E)-isomer being prepared by standard Wittig chemistry. Reduction of each allylic ester, with diisobutylaluminium hydride (DIBAL), gave the allylic alcohols (15) and (19), respectively. Epoxidation of (15) and (19), under Sharpless conditions, gave separate samples of all four stereoisomers of 2,3-epoxy-5-phenylpentan-1-ol. Esterification of each isomer with Cbz-valine, under Mitsunobu conditions, provided (9)-(12) which were assayed against HIV protease. The cis series (9)-(10) proved to be significantly more potent than the trans (11)-12) and, within each of these series, the isomers derived from L-diisopropyltartrate [(9) and (11)] were the most active.

1,3-Dimethyl 2-oxo 1,3,2-diazaphospholidine precursor of (Z) α,β-unsaturated esters

α,β-Unsaturated esters of (Z) geometry are selectively obtained from cyclic phosphonocarboxylates derived from N,N'-dimethylethylenediamine.