110-93-0

Basic information

• Product Name: 6-Methyl-5-hepten-2-one
• Synonyms: 2-Methyl-6-oxo-2-heptene;2-methylhept-2-en-6-one;2-Oxo-6-methylhept-5-ene;5-Hepten-2-one,6-methyl-;6-methyI-5-hepten-2-one;6-methyl-5-hepten-2-on;6-Methyl-5-hepten-2-one,(2-2-6);6-methylhept-
• CAS NO: 110-93-0
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.2
• EINECS: 203-816-7
• Product Categories: Alphabetical Listings;Certified Natural ProductsFlavors and Fragrances;Flavors and Fragrances;M-N;C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 110-93-0.mol
• Article Data: 102

Chemical Properties

• Melting Point: -67.1 °C
• Boiling Point: 73 °C18 mm Hg(lit.)
• Flash Point: 123 °F
• Appearance: Clear slightly yellow liquid
• Density: 0.855 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.121hPa at 20℃
• Refractive Index: n20/D 1.439(lit.)
• Storage Temp.: Flammables area
• Solubility: Soluble in methanol and chloroform.
• Explosive Limit: 1.1-7.3%(V)
• Water Solubility: insoluble
• BRN: 1741705
• CAS DataBase Reference: 6-Methyl-5-hepten-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methyl-5-hepten-2-one(110-93-0)
• EPA Substance Registry System: 6-Methyl-5-hepten-2-one(110-93-0)

Safety Data

• Statements: 10-36/37/38
• Safety Statements: 16-24/25
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 1
• RTECS: MJ9700000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 110-93-0(Hazardous Substances Data)

Usage

Description

6-Methyl-5-hepten-2-one has a strong, fatty, green, citrus-like odor, and a bittersweet taste reminiscent of pear. May be prepared from oil of lemongrass or from citral by refluxing for 12 hours in aqueous solution containing K2C 03, and subsequent distillation and vacuum fractionation; from acetoacetic ester and methylbuten-3-ol-2 with aluminum alcoholate in Carroll’s reaction followed by pyrolysis of the ester.

Chemical Properties

Different sources of media describe the Chemical Properties of 110-93-0 differently. You can refer to the following data:
1. 6-Methyl-5-hepten-2-one has a strong, fatty, green, citrus-like odor and bittersweet taste reminiscent of pear.
2. CLEAR SLIGHTLY YELLOW LIQUID
3. 6-Methyl-5-hepten-2-one is an important intermediate in the synthesis of terpenoids. Its odor properties are not impressive. It occurs in nature as a degradation product of terpenes. (Z)- and (E)-Tagetone, [3588-18-9], [6752-80-3], are major components of tagetes oil. Solanone [1937-54-8] and pseudoionone [141-10-6] are acyclicC13 ketoneswith a terpenoid skeleton. Solanone is one of the flavor-determining constituents of tobacco, and pseudoionone is an intermediate in the synthesis of ionones.

Occurrence

Originally identified in lemongrass; it has been reported found in the essential oils of palmarosa, lemon, citronella, vervain, geranium, Ocimum canum, Artemisia scoparia, Urtica dioica and others. Also reported found in apple, apricot, sweet and sour cherry, orange juice, citrus peel oils, bilberry, lingonberry, cranberry, guava, grapes, melon, peach, pear, raspberry, strawberry, blackberry, carrot, celery, tomato, potato, clove bud and leaf, ginger, peppermint oil, thymus, Gruyere cheese, butter, beef, hop oil, beer, cognac, cider, white wine, cocoa, tea, peanut oil, avocado, Arctic bramble, cloudberry, olive, passion fruit, plumcot, rose apple, marjoram, starfruit, mango, fig, rice, rice bran, quince, origanum, calamus, buckwheat, corn oil, wort, dried bonito, elderberry, cherimoya, kiwifruit, mountain papaya, endive, lemon balm, clary sage, nectarine, clam, Cape gooseberry, maté, German chamomile oil and mastic gum leaf oil, lime oil and apple brandy

Uses

Different sources of media describe the Uses of 110-93-0 differently. You can refer to the following data:
1. 6-Methyl-hepten-2-one is used in the synthesis of thyrsiferyl 23-Acetate which acts as an anti-leukemic inducer of apoptosis.
2. Organic synthesis, inexpensive perfumes, fla-voring.

Definition

ChEBI: A heptenone that is hept-5-en-2-one substituted by a methyl group at position 6. It is a volatile oil component of citronella oil, lemon-grass oil and palmarosa oil.

Preparation

From oil of lemongrass or from citral by refluxing for 12 hours in aqueous solution containing K2CO3, and subsequent distillation and vacuum fractionation; from acetoacetic ester and methyl-buten-3-ol-2 with aluminum alcoholate in Carroll’s reaction followed by pyrolysis of the ester

Aroma threshold values

Detection: 50 ppb

Taste threshold values

Taste characteristics at 10 ppm: green, vegetative, musty, apple, banana and green bean-like.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 4893, 1987 DOI: 10.1016/S0040-4039(00)96654-1Synthesis, p. 796, 1981 DOI: 10.1055/s-1981-29599

General Description

6-Methyl-5-hepten-2-one is one of the main flavor volatile of tomatoes.

Flammability and Explosibility

Flammable

Safety Profile

Moderately toxic by ingestion. A skin irritant. Flammable liquid when exposed to heat, sparks, or flame. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C8H14O/c1-7(2)5-4-6-8(3)9/h5H,4,6H2,1-3H3

Synthetic route

3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8) + 2-methyl-but-3-yn-2-ol (115-19-5) → 6-Methyl-hept-5-en-2-on (110-93-0) + acetone (67-64-1)

Conditions	Yield
potassium hydroxide In water at 93℃; for 6.41667h; Heating / reflux;	A 95.2% B 95.8%

2-methyl-3-buten-2-ol (115-18-4) + 2-Methoxypropene (116-11-0) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With Dimethyl phosphite at 150℃; for 14.6h; Reagent/catalyst; Time; Inert atmosphere;	95.1%
hydrogen tris(oxalato)phosphate In methanol at 124.84 - 149.84℃; for 17 - 25h; Product distribution / selectivity;	77.3%
hydrogen tris(oxalato)phosphate In acetone at 149.84℃; for 24h; Product distribution / selectivity;	56.4%

6-methylhept-5-en-2-one N,N-dimethylhydrazone (74596-83-1) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With sodium perborate; sodium hydroxide; potassium dihydrogenphosphate; water In tert-butyl alcohol at 60℃; for 24h;	94%

3-chloro-3-methyl-1-butene (2190-48-9) + 3,3-dimethyl-allyl chloride (503-60-6) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With N,N-dimethyl-formamide; sodium hydroxide In acetone at 50℃; for 2h; Reagent/catalyst; Temperature; Inert atmosphere;	92.8%

4-((E)-2,6-Dimethyl-hepta-1,5-dienyl)-morpholine → 4-morpholinecarboxaldehyde (4394-85-8) + 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With aluminum oxide; potassium permanganate; neutral In acetone for 4h; Ambient temperature;	A n/a B 92%

(E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → 6-Methyl-hept-5-en-2-on (110-93-0) + acetaldehyde (75-07-0)

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide; water at 150℃; for 0.166667h; Microwave irradiation; Green chemistry;	A 91% B n/a
With potassium carbonate

2-methyl-3-buten-2-ol (115-18-4) + acetoacetic acid methyl ester (105-45-3) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
	90.8%

(E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With pyrrolidine; water In acetonitrile at 20℃; for 12h;	90%
With water; potassium carbonate man destilliert mit Wasserdampf und fraktioniert im Vakuum;
With potassium carbonate

C14H26N2O → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With selenium(IV) oxide; dihydrogen peroxide In methanol at 20℃; pH=7; aq. phosphate buffer;	89%

1,2-diamino-benzene (95-54-5) + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → 2-Methyl-1H-benzimidazole (615-15-6) + 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide; water at 150℃; for 0.166667h; Microwave irradiation; Green chemistry;	A 61% B 89%

2-methyl-2-(4-methyl-3-pentenyl)-1,3-dioxolane (3695-38-3) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With polymer-supported dicyanoketene acetal; water at 20℃; for 20h;	88%
With silica gel; toluene-4-sulfonic acid In dichloromethane for 3h;	87%
With polymer-supported dicyanoketene acetal; water In acetonitrile at 20℃; for 20h; Hydrolysis;	73%
palladium (II) ion In acetone for 1h; Ambient temperature;	100 % Chromat.

C10H17NO2 → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
Stage #1: C10H17NO2 With chromium dichloride; acrylic acid methyl ester In tetrahydrofuran at 25℃; Stage #2: With water In tetrahydrofuran Further stages.;	88%

2-Methoxypropene (116-11-0) + 3-(1-methoxy-1-methyl-ethoxy)-3-methyl-but-1-ene (1196448-62-0) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
Stage #1: 3-(1-methoxy-1-methyl-ethoxy)-3-methyl-but-1-ene at 150℃; for 16h; autoclave; Stage #2: 2-Methoxypropene; phosphoric acid In acetone at 150℃; for 16h; autoclave;	86%

6-methylhept-5-en-2-ol (4630-06-2, 1569-60-4) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With trimethylsilyl chromates In dichloromethane at 25℃; for 2h;	85%
With butyltriphenylphosphonium dichromate In chloroform for 3.5h; Oxidation; Heating;	80%
With [Fe[(S)-N-benzyl-2-phenyl-2-(pyridin-2-ylmethoxy)-N-(pyridin-2-ylmethyl)ethanamine](OTf)2]; dihydrogen peroxide In water; acetonitrile at 20℃; for 2h; Inert atmosphere;	69%

6-Methyl-3-(toluene-4-sulfonyl)-hept-5-en-2-one (80868-07-1) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With disodium hydrogenphosphate; sodium amalgam In methanol at 0℃; for 2h;	85%

4-<(tert-Butyl)dimethylsilyl>-2-methyl-2-(4'-methylpent-3'-enyl)-1,3-dioxole (140458-17-9) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With water; oxalic acid Ambient temperature;	85%

1,1-dimethylprop-2-enyl 3-oxobutanoate (15973-38-3) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With aluminum oxide at 60℃; for 3h;	84%
With aluminum oxide at 60℃; for 3h; Product distribution; substrate supported on Al2O3; Carrol rearrangement of allyl acetoacetates to γ,δ-unsaturated ketones on the surface of chromatographic absorbents;	84%
With aluminum isopropoxide at 160℃;

3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8) + 2-methylpropan-2-thiol (75-66-1) → 6-Methyl-hept-5-en-2-on (110-93-0) + (Z)-1-tert-Butylsulfanyl-3,7-dimethyl-octa-1,6-dien-3-ol (86254-75-3)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 50℃; for 6h;	A 10% B 83%
With potassium hydroxide In dimethyl sulfoxide at 50℃; for 6h;	A 10% B 83%

6-methylhept-5-en-2-one oxime (22418-73-1) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With tert.-butylhydroperoxide; dipyridinium dichromate In dichloromethane at 0℃; for 4.5h;	80%

2,4-Dimethyl-2-(4'-methylpent-3'-enyl)-1,3-dioxole (140458-18-0) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With hydrogenchloride for 24h;	80%

(E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → 6-Methyl-hept-5-en-2-on (110-93-0) + 4,6-bis(4-methylpent-3-en-1-yl)-6-methylcyclohexa-1,3-diene-1-carbaldehyde (61447-89-0, 474779-14-1)

Conditions	Yield
With sodium hydride In diethyl ether for 0.5h; Heating;	A n/a B 80%

6-methylhept-5-en-2-ol (4630-06-2, 1569-60-4) → 6-Methyl-hept-5-en-2-on (110-93-0) + 6-methylhept-6-en-2-one (10408-15-8) + 6-methylheptan-2-one (928-68-7)

Conditions	Yield
With reusable unsupported rhenium nanocrystalline particle In neat (no solvent) at 180℃; for 10h; Green chemistry;	A 80% B 5% C 15%

3-(1-methoxy-1-methyl-ethoxy)-3-methyl-but-1-ene (1196448-62-0) + 2,2-dimethoxy-propane (77-76-9) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
phosphoric acid In acetone at 150℃; for 32h; Product distribution / selectivity; autoclave;	78.8%

2,3-epoxygeranial (16996-12-6) → 2-methyl-2-(4-methyl-pent-3-enyl)-oxirane (50340-32-4) + 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-benzene at 140℃; for 14h; Sealed tube; Inert atmosphere;	A 73% B 23%

tert-butyl acetoacetate (1694-31-1) + 2-methyl-3-buten-2-ol (115-18-4) → 6-Methyl-hept-5-en-2-on (110-93-0) + 1,1-dimethylprop-2-enyl 3-oxobutanoate (15973-38-3)

Conditions	Yield
In toluene for 4h; Heating;	A 31% B 72%

1,1-dimethylprop-2-enyl 3-oxobutanoate (15973-38-3) → 6-Methyl-hept-5-en-2-on (110-93-0) + 3-methylbut-2-en-1-yl 3-oxobutanoate (21597-32-0)

Conditions	Yield
With silica gel at 60℃; for 5h;	A n/a B 70%

5-methyl-4-hexenenitrile (23089-87-4) + methyllithium (917-54-4) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
In diethyl ether at 0℃; for 3h;	70%
In diethyl ether at 0℃; for 1h; Methylation;	70%

3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8) + 3-tert-Butylsulfanyl-but-3-en-2-ol (86254-77-5) → 6-Methyl-hept-5-en-2-on (110-93-0) + (Z)-1-tert-Butylsulfanyl-3,7-dimethyl-octa-1,6-dien-3-ol (86254-75-3)

Conditions	Yield
With potassium hydroxide In neat (no solvent) at 75 - 120℃; for 0.366667h;	A 33% B 64%

2-methyl-3-buten-2-ol (115-18-4) + ethyl acetoacetate (141-97-9) → 6-Methyl-hept-5-en-2-on (110-93-0) + 3-methylbut-2-en-1-yl 3-oxobutanoate (21597-32-0)

Conditions	Yield
In paraffin 1.) 160 deg C, 6 h, 2.) 180 deg C, 3 h;	A 60% B 5%

3-(1-methoxy-1-methyl-ethoxy)-3-methyl-but-1-ene (1196448-62-0) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
Stage #1: 3-(1-methoxy-1-methyl-ethoxy)-3-methyl-but-1-ene at 150℃; for 16h; autoclave; Stage #2: phosphoric acid In acetone at 150℃; for 16h; autoclave;	60%

6-Methyl-hept-5-en-2-on (110-93-0) → 6-methylhept-5-en-2-ol (4630-06-2, 1569-60-4)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1h;	100%
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1h;	99%
With hydrogen; silver trifluoromethanesulfonate; potassium hexamethylsilazane In toluene at 25℃; under 15001.5 Torr; for 24h; Glovebox; chemoselective reaction;	99%

6-Methyl-hept-5-en-2-on (110-93-0) → (S)-sulcatol (58917-26-3)

Conditions	Yield
In isopropyl alcohol at 50℃; for 24h; ADH T. brockii (growing), NADP, PAN 800;	100%
With NADH-dependent-formate-dehydrogenase; flavin adenine dinucleotide; NADH at 30℃; for 6h; pH=7.5; aq. buffer; Enzymatic reaction; optical yield given as %ee; enantiospecific reaction;	99%
With dichloro(benzene)ruthenium(II) dimer; mono(3-deoxy-3-[N-(2-hydroxyethyl)amino])-β-cyclodextrin; sodium formate In water; N,N-dimethyl-formamide at 50℃; for 12h; optical yield given as %ee; enantioselective reaction;	95%

6-Methyl-hept-5-en-2-on (110-93-0) + acetylene (74-86-2) → 3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8)

Conditions	Yield
With sodium methylate In methanol at 0 - 5℃; for 0.5h; Inert atmosphere;	99.1%
	86%
With diethyl ether unter Zusatz von Kaliumhydroxid;

6-Methyl-hept-5-en-2-on (110-93-0) → 6-methylheptan-2-one (928-68-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate under 2280 Torr; for 0.75h; Ambient temperature;	99%
With hydrogen In tetrahydrofuran at 24.84℃; under 15001.5 Torr; for 1h;	98.2%
With hydrogen; palladium/alumina at 60℃; under 1500.15 Torr; for 66h; Product distribution / selectivity; Autoclave;	97.3%

6-Methyl-hept-5-en-2-on (110-93-0) + 1,2-diamino-benzene (95-54-5) → 2-methyl-2,4-di(4-methyl-3-pentenyl)-2,3-dihydro-1H-1,5-benzodiazepine

Conditions	Yield
With ytterbium(III) triflate at 20℃; for 4h;	99%

6-Methyl-hept-5-en-2-on (110-93-0) + ketene t-butyldimethylsilyl methyl acetal (77086-38-5) → methyl 3-((tert-butyldimethylsilyl)oxy)-3,7-dimethyloct-6-enoate

Conditions	Yield
Stage #1: 6-Methyl-hept-5-en-2-on With bis(trifluoromethanesulfonyl)amide In diethyl ether at -78 - 23℃; Mukaiyama Aldol Addition; Schlenk technique; Inert atmosphere; Stage #2: ketene t-butyldimethylsilyl methyl acetal In diethyl ether at -20℃; for 0.5h; Mukaiyama Aldol Addition; Schlenk technique; Inert atmosphere;	99%

6-Methyl-hept-5-en-2-on (110-93-0) + trimethylsulfonium methylsulfate (2181-44-4) → 2-methyl-2-(4-methyl-pent-3-enyl)-oxirane (50340-32-4)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In dichloromethane	98%

6-Methyl-hept-5-en-2-on (110-93-0) + 4-methoxy-aniline (104-94-9) → 4-methoxy-N-(6-methylhept-5-en-2-yl)aniline

Conditions	Yield
With formic acid; chloro-(pentamethylcyclopentadienyl)-{5-methoxy-2-{1-[(4-methoxyphenyl)imino-N]ethyl}phenyl-C}-iridium(lll); triethylamine In methanol at 80℃; for 1h; Inert atmosphere;	97%

Vinyl bromide (593-60-2) + 6-Methyl-hept-5-en-2-on (110-93-0) → 2-bromo-3,7-dimethylocta-1,6-dien-3-ol

Conditions	Yield
Stage #1: Vinyl bromide With n-butyllithium; lithium bromide In tetrahydrofuran; diethyl ether; pentane at -127 - -105℃; for 3h; Inert atmosphere; Schlenk technique; Stage #2: 6-Methyl-hept-5-en-2-on In tetrahydrofuran; diethyl ether; pentane Inert atmosphere; Schlenk technique;	97%

6-Methyl-hept-5-en-2-on (110-93-0) + vinylmagnesium chloride (3536-96-7) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6)

Conditions	Yield
With zinc(II) chloride In tetrahydrofuran at 20℃; for 4h; Reagent/catalyst; Solvent; Inert atmosphere; Cooling with ice;	96.3%
With tetrahydrofuran

6-Methyl-hept-5-en-2-on (110-93-0) + ethylene glycol (107-21-1) → 2-methyl-2-(4-methyl-3-pentenyl)-1,3-dioxolane (3695-38-3)

Conditions	Yield
With pyridinium p-toluenesulfonate In benzene Heating;	96%
With toluene-4-sulfonic acid In benzene	94%
With toluene-4-sulfonic acid In benzene for 5h; Condensation; Heating;	92%

6-Methyl-hept-5-en-2-on (110-93-0) + 2-propynyl chloride (624-65-7) → 4,8-dimethyl-non-7-en-1-yn-4-ol (71869-02-8)

Conditions	Yield
With manganese; TiCpCl2 In tetrahydrofuran at 20℃; for 1h; Reagent/catalyst; Inert atmosphere;	96%
With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 7h; Barbier Coupling Reaction; Inert atmosphere; chemoselective reaction;	96%

dimethyltitanocene (1271-66-5) + 6-Methyl-hept-5-en-2-on (110-93-0) → 2,6-dimethyl-hepta-1,5-diene (6709-39-3)

Conditions	Yield
Stage #1: dimethyltitanocene; 6-Methyl-hept-5-en-2-on In toluene at 20 - 80℃; for 5h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In methanol; water; toluene at 40℃; for 3h; Temperature;	95.3%

6-Methyl-hept-5-en-2-on (110-93-0) + vinyl magnesium bromide (1826-67-1) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6)

Conditions	Yield
With zinc(II) chloride In tetrahydrofuran at 20℃; for 5h; Reagent/catalyst; Solvent; Inert atmosphere; Cooling with ice;	95.2%
With tetrahydrofuran; diethyl ether
In tetrahydrofuran at -78℃; Addition;

methyl magnesium iodide (917-64-6) + 6-Methyl-hept-5-en-2-on (110-93-0) → 2,6-dimethylhept-5-en-2-ol (6090-15-9)

Conditions	Yield
In diethyl ether for 1h;	95%
analog verlaeuft die Reaktion mit Magnesiumaethyljodid;

6-Methyl-hept-5-en-2-on (110-93-0) + ethyl bromoacetate (105-36-2) → 3-hydroxy-3,7-dimethyl-oct-6-enoic acid ethyl ester (54211-39-1)

Conditions	Yield
With zinc In tetrahydrofuran for 2h; Reformatsky Reaction; Reflux;	95%
With zinc In tetrahydrofuran for 2h; Reformatsky Reaction; Reflux;	95%
With zinc In tetrahydrofuran for 2h; Reformatsky Reaction; Reflux;	95%

chloro-trimethyl-silane (75-77-4) + 6-Methyl-hept-5-en-2-on (110-93-0) → 6-methylhept-5-en-2-yl trimethylsilyl ether (84569-39-1)

Conditions	Yield
With tert-Amyl alcohol; sodium hydride; zinc(II) chloride In tetrahydrofuran for 0.25h; Ambient temperature;	95%

Methyl 2-bromopropionate (5445-17-0) + 6-Methyl-hept-5-en-2-on (110-93-0) → 2,3-Dimethyl-3-(4-methyl-pent-3-enyl)-oxirane-2-carboxylic acid methyl ester

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃;	95%

6-Methyl-hept-5-en-2-on (110-93-0) + acetylenemagnesium bromide (4301-14-8) → 3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8)

Conditions	Yield
In tetrahydrofuran at 0℃; for 1h;	95%
In tetrahydrofuran; diethyl ether Grignard reaction;	90%
In tetrahydrofuran at -78 - 20℃;	87%

6-Methyl-hept-5-en-2-on (110-93-0) + α-halo acetic acid ethyl ester → 3-hydroxy-3,7-dimethyl-oct-6-enoic acid ethyl ester (54211-39-1)

Conditions	Yield
With zinc Reformatsky reaction;	95%

6-Methyl-hept-5-en-2-on (110-93-0) → C8H14O3

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; trifluoroacetic acid In dichloromethane at 0℃; for 6h;	95%

6-Methyl-hept-5-en-2-on (110-93-0) → (RS)-6-methylhept-5-en-2-ol

Conditions	Yield
With methanol; sodium tetrahydroborate at 0 - 35℃;	95%

trimethylsilyl cyanide (7677-24-9) + 6-Methyl-hept-5-en-2-on (110-93-0) → C12H23NOSi

Conditions	Yield
Stage #1: 6-Methyl-hept-5-en-2-on With (R,R)-N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminoaluminum(III) chloride; (tert-Butoxycarbonylmethylene)triphenylphosphorane; Triphenylphosphine oxide In dichloromethane at -30℃; for 0.5h; Inert atmosphere; Stage #2: trimethylsilyl cyanide In dichloromethane at -30℃; for 20h; Inert atmosphere;	95%
With (R,R)-N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminoaluminum(III) chloride; ethyl (triphenylphosphoranylidene)acetate In ethyl acetate at -30℃; for 33h; Solvent; Inert atmosphere;	92%

6-Methyl-hept-5-en-2-on (110-93-0) → 5,6-dihydroxy-6-methyl-heptan-2-one (16194-30-2)

Conditions	Yield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone; tert-butyl alcohol at 0℃; for 4h;	94%
With water; oxygen bei der Sonnenbelichtung;
With potassium permanganate; water
With potassium permanganate

6-Methyl-hept-5-en-2-on (110-93-0) + N,N-Bis(trimethylsilyl)benzenesulphenamide (17745-52-7) → N-<(6-methyl)-5-hepten-2-ylidene>benzenesulfenamide (130485-93-7)

Conditions	Yield
tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;	94%

6-Methyl-hept-5-en-2-on (110-93-0) + 1,1-dimethylhydrazine (57-14-7) → 6-methylhept-5-en-2-one N,N-dimethylhydrazone (74596-83-1)

Conditions	Yield
With acetic acid at 20℃; for 3h; Condensation;	94%
Yield given;

6-Methyl-hept-5-en-2-on (110-93-0) + dimethyl methane phosphonate (756-79-6) → (2-hydroxy-2,6-dimethyl-hept-5-enyl)-phosphonic acid dimethyl ester

Conditions	Yield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.25h; Stage #2: 6-Methyl-hept-5-en-2-on In tetrahydrofuran; hexane for 0.0833333h; Further stages.;	94%

Upstream product

• 24443-15-0 1,3-dibromo-3-methylbutane 
• 15435-71-9 sodium acetylacetonate 
• 87386-18-3 5,9-dimethyl-dec-8-en-5-ol 
• 15973-38-3 acetoacetate of dimethylvinyl carbinol 
• 855902-75-9 2-hydroxy-2,6-dimethyl-hept-5-enoic acid 
• 1694-31-1 tert-butyl acetoacetate 
• 115-18-4 2-methyl-3-buten-2-ol 
• 23089-87-4 5-methyl-4-hexenenitrile 
• 917-54-4 methyllithium 
• 141-97-9 ethyl acetoacetate 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 74596-84-2 7-methyloct-6-en-3-one N,N-dimethylhydrazone 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 502-65-8 lycopene 

Downstream Products

• 6617-30-7 (+/-)-2,2-dimethyl-3t-(3-oxo-butyl)-cyclopropane-carboxylic acid-(1r) 
• 6617-30-7 cis-(dl)-1,1-dimethyl-2-(3'-oxobutyl)-cyclopropane-3-carboxylic acid 
• 6090-15-9 2,6-dimethylhept-5-en-2-ol 
• 182412-80-2 7-methyl-3,4-dimethyleneoct-6-en-2-one 
• 58461-27-1 (+/-)-lavandulol 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 15719-64-9 methylammonium carbonate 
• 67-64-1 acetone 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 18479-51-1 dihydrolinalool 
• 84912-18-5 2,5,9-trimethyl-dec-8-en-5-ol 
• 29171-20-8 3,7-dimethyloct-6-en-1-yn-3-ol 
• 101604-15-3 3-benzyloxy-3,7-dimethyloct-6-en-1-yne 

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