7086-79-5

Basic information

• Product Name: 3-isopropenyl-6-oxoheptanal (IPOH)
• Synonyms: 3-isopropenyl-6-oxoheptanal (IPOH);3-(1-Methylethenyl)-6-oxoheptanal;3-Isopropenyl-6-oxoheptanal;Limononaldehyde;3-Isopropyl-6-oxoheptanal;Heptanal, 3-(1-Methylethenyl)-6-oxo-
• CAS NO: 7086-79-5
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.24
• Mol File: 7086-79-5.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 270℃
• Flash Point: 100℃
• Appearance: /
• Density: 0.917
• Vapor Pressure: 0.00715mmHg at 25°C
• Refractive Index: 1.437
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-isopropenyl-6-oxoheptanal (IPOH)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-isopropenyl-6-oxoheptanal (IPOH)(7086-79-5)
• EPA Substance Registry System: 3-isopropenyl-6-oxoheptanal (IPOH)(7086-79-5)

Safety Data

• Hazardous Substances Data: 7086-79-5(Hazardous Substances Data)

Usage

General Description

3-isopropenyl-6-oxoheptanal (IPOH) is a semi-volatile organic compound known for its unique chemical properties. Its use in scientific research is relatively new, and thus little is known about its safety or potential applications. The chemical structure is characterized by its aldehyde function and its conjugated system. It is highly reactive due to the presence of both an alkene and carbonyl functional groups, lending itself well to a variety of chemical transformations. The compound is typically synthesized via organic synthesis techniques, but details regarding its production and potential uses in industry or academia are still under study.

InChI:InChI=1/C10H16O2/c1-8(2)10(6-7-11)5-4-9(3)12/h7,10H,1,4-6H2,2-3H3

Upstream product

• 5989-27-5 D-limonene 
• 185197-78-8 3-methyl-3-(3-methylethenyl-5-oxopentyl)-1,2,4-trioxolane 
• 185329-56-0 1-methyl-4-(1-methylethenyl)-1,2-cyclohexanediol 
• 1195-92-2 (4R)-limonene 1,2-epoxide 
• 203719-53-3 (-)-limonene oxide 
• 1361327-90-3 (4S)-1-methyl-4-(prop-1-en-2-yl)-7,8,9-trioxabicyclo[4.2.1]nonane 
• 5989-54-8 (-)-(S)-limonene 

Downstream Products

• 85031-78-3 1-((S)-4-Isopropenyl-cyclopent-1-enyl)-ethanone 
• 362056-98-2 1-((S)-5-Isopropenyl-2-methyl-cyclopent-1-enylmethoxy)-3-methyl-benzene 
• 64309-03-1 (3RS,6R)-3-methyl-6-(1-methylethenyl)dec-9-en-1-yl acetate 
• 1298063-22-5 (2S)-5-methyl-2-(prop-1-en-2-yl)hex-5-enyl acetate 
• 144831-70-9 (2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-enyl acetate 
• 1330048-79-7 C₁₀H₁₈O 
• 50373-53-0 (2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol 
• 1327155-04-3 C₁₂H₂₀O₂ 
• 20777-39-3 (-)-(R)-lavanduyl acetate 
• 498-16-8 (R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol 
• 1330048-77-5 C₁₀H₁₈O 
• 1361327-96-9 (3S)-6-hydroxyimino-1-methoxy-3-(prop-1-en-2-yl)heptan-1-ol 
• 1361327-92-5 methyl [(1S)-2,4-dimethoxy-2,4-dimethylcyclohexyl]acetate 
• 67225-47-2 (3Z,6R)-3-methyl-6-(1-methylethenyl)-3,9-decadien-1-yl acetate 

Relevant articles and documents

Iron-catalyzed chemoselective hydride transfer reactions

A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.

Synthesis of 12-epi-Protopanaxadiol and Formal Synthesis of Ginsenoside Chikusetsusaponin-LT8

In the context of the total synthesis of protopanaxadiol, two strategies were explored. One strategy from an optically active trienic epoxide, possessing a 5-membered ring, prepared from (S)-epoxy-limonene and (S)-epoxyfarnesol, which was submitted to Ti-(III)-mediated radical cascade to afford an original tetracyclic structure resulting from a 6-endo-trig 6-endo-trig 8-endo-trig process. A second strategy, starting from a Wieland-Miescher-type ketone, using a “ring-by-ring” synthesis allowed the synthesis of 12-epi-protopanaxadiol. In this latter strategy, an efficient sequence of reactions to install the two vicinal C8–C14 quaternary centers involves: i) a Barbier type reaction; ii) an oxidative allylic transposition and iii) a nickel-catalyzed addition of trimethylaluminium. By using this second strategy, 20-hydroxydammar-24-ene-3,12-dione was synthesized which represents a formal synthesis of chikusetsusaponin-LT8, isolated from Panax japonicus.

Ozonolytic Transformations of (S)-(–)-Limonene and Abietic Acid in the Presence of Pyridine

Controlled ozonolysis of (S)-(–)-limonene in the presence of Py gave 4-methyl-3-(3-oxobutyl)pent-4-enal or 4-methyl-3-(3-oxobutyl)pent-4-enoic acid depending on the solvent (CH2Cl2 or MeOH). Exhaustive ozonolysis produced 3-acetyl-6-oxoheptanoic acid. Ozonolysis of abietic acid in CH2Cl2 in the presence of Py formed stable epoxytrioxolaneabietic acid; in MeOH–Py, the epoxyketoaldehyde corresponding to cleavage of the C13–C14 bond.