472-66-2

Basic information

• Product Name: 2,6,6-TRIMETHYL-1-CYCLOHEXENE-1-ACETALDEHYDE
• Synonyms: (2,6,6-Trimethyl-1-cyclohexen-1-yl)acetaldehyde;2,6,6-trimethyl-1-cyclohexene-1-acetaldehyd;B-HOMOCYCLOCITRAL;FEMA 3474;2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-ACETALDEHYDE;2,6,6-TRIMETHYL-1-CYCLOHEXENE-1-ACETALDEHYDE;2 6 6-TRIMETHYL-1-CYCLOHEXENE-1-ACET- &;2,6,6-TRIMETHYL-1-CYCLOHEXENE-1-ACETALDE HYDE, TECH., 80%
• CAS NO: 472-66-2
• Molecular Formula: C₁₁H₁₈O
• Molecular Weight: 166.26
• EINECS: 207-454-0
• Product Categories: Aldehydes;Building Blocks;C10-C12;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 472-66-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 58-59 °C0.4 mm Hg(lit.)
• Flash Point: 191 °F
• Appearance: /
• Density: 0.941 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0324mmHg at 25°C
• Refractive Index: n20/D 1.485(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,6,6-TRIMETHYL-1-CYCLOHEXENE-1-ACETALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6,6-TRIMETHYL-1-CYCLOHEXENE-1-ACETALDEHYDE(472-66-2)
• EPA Substance Registry System: 2,6,6-TRIMETHYL-1-CYCLOHEXENE-1-ACETALDEHYDE(472-66-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 472-66-2(Hazardous Substances Data)

Usage

Uses

2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde can be used as a starting material to prepare: (±)-Aeginetolide by oxidation in the presence of meta-chloroperoxybenzoic acid (m-CPBA). (±)-Dihydroactinidiolide (a C11-terpenic lactone) via dehydration of key intermediate aeginetolide. It can also be used as a key intermediate to synthesize drimane-related sesquiterpenes and substituted retinoic acid analogs.

Taste threshold values

Taste characteristics at 15 ppm: cooling, woody, oily, soapy, citrus with a berry, orris-like nuance.

InChI:InChI=1/C11H18O/c1-9-5-4-7-11(2,3)10(9)6-8-12/h8H,4-7H2,1-3H3

Synthetic route

2-((E)-2-Methoxy-vinyl)-1,3,3-trimethyl-cyclohexene (86558-54-5, 86558-55-6) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
With perchloric acid In tetrahydrofuran for 0.5h; Ambient temperature;	94%

2,2,6-trimethylcyclohexan-1-one (2408-37-9) + Bromoacetaldehyde diethyl acetal (2032-35-1) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
Stage #1: Bromoacetaldehyde diethyl acetal With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 3.25h; Inert atmosphere; Stage #2: 2,2,6-trimethylcyclohexan-1-one In tetrahydrofuran at 10 - 15℃; for 3h;	93.7%

2-bromomethyl-1,3-dioxolane (4360-63-8) + 2,2,6-trimethylcyclohexan-1-one (2408-37-9) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
Stage #1: 2-bromomethyl-1,3-dioxolane With iodine; magnesium In 2-methyltetrahydrofuran at 30 - 40℃; for 3.25h; Inert atmosphere; Stage #2: 2,2,6-trimethylcyclohexan-1-one In 2-methyltetrahydrofuran at 10 - 15℃; for 3h;	93.1%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 2,2,6-trimethylcyclohexan-1-one (2408-37-9) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
Stage #1: 1-bromo-2,2-dimethoxyethane With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 3.25h; Inert atmosphere; Stage #2: 2,2,6-trimethylcyclohexan-1-one In tetrahydrofuran at 10 - 15℃; for 3h; Temperature; Solvent;	92.8%

chloroacetaldehyde dimethyl acetal (97-97-2) + 2,2,6-trimethylcyclohexan-1-one (2408-37-9) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
Stage #1: chloroacetaldehyde dimethyl acetal With iodine; magnesium In ethylene dibromide at 30 - 45℃; for 3.41667h; Inert atmosphere; Stage #2: 2,2,6-trimethylcyclohexan-1-one In ethylene dibromide at 10 - 15℃; for 3h;	90.7%

1-((E)-2-Methoxy-vinyl)-6,6-dimethyl-cyclohexene → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
With perchloric acid In diethyl ether for 5h;	78.9%

α--2,6,6,-trimethyl-1-cyclohexenemethanol (128463-60-5) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
With formic acid for 0.166667h; Ambient temperature;	75%

1-ethoxyethynyl-2,2,6-trimethyl-cyclohexanol (408511-80-8) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
With quinoline; Petroleum ether bei partieller Hydrierung an bleihaltigem Palladium, anschl. mit wss. H2SO4;

2-acetoxyvinylidene-1,1,3-trimethyl-cyclohexane (87570-49-8, 100678-90-8) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
With hydrogenchloride; water

1-ethynyl-2,2,6-trimethyl-1-cyclohexanol (41613-59-6) + ethanethiol (75-08-1) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
In tetrachloromethane (i) AIBN, (irradiation), (ii) CF3CO2H; Multistep reaction;

1-ethynyl-2,2,6-trimethyl-1-cyclohexanol (41613-59-6) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
With vanadium tri-n-propoxide; benzoic acid; triphenylhydroxysilane In various solvent(s) at 140 - 150℃;	81 % Turnov.

1-ethynyl-2,2,6-trimethyl-1-cyclohexanol (41613-59-6) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) + α-(2,6,6-Trimethyl-1-cyclohexenyl)acetaldehyd (100513-69-7)

Conditions	Yield
tetrabutoxytitanium; p-Toluic acid; copper(l) chloride In 1,2-dichloro-benzene at 130℃; for 4h; Title compound not separated from byproducts;

(E)-3-(2,6,6-trimethylcyclohex-1-enyl)acrylic acid (14393-45-4) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
With hydrogenchloride; diphenyl phosphoryl azide; triethylamine 1) dioxan, RT, 1 h, 2.) reflux, 15 min; Yield given. Multistep reaction;

2,2,6-trimethylcyclohexan-1-one (2408-37-9) + lithium acetylide-ethylenediamine complex (1216963-74-4) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
(i), (ii) Ph3SiOH, (iii) (Ph3SiO)3VO; Multistep reaction;

1-acetoxy-2-<2,6,6-trimethyl-cyclohex-1-enyl>-ethene → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
With methanol; water; sodium hydrogencarbonate

1-ethoxy-2-<2,6,6-trimethyl-cyclohex-1-enyl>-ethene → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
With ethanol; water; toluene-4-sulfonic acid

(E)-β-ionone (79-77-6) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / NaOH, Br2 / H2O; dioxane / 4 h / Ambient temperature 2: 1.) Et3N, diphenyl phosphoryl azide, 2.) 0.5 N aq. HCl / 1) dioxan, RT, 1 h, 2.) reflux, 15 min View Scheme

2,6,6-trimethylcyclohex-1-enecarbaldehyde (432-25-7) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: s-BuLi / 1.) THF, hexane, from -70 deg C to -25 deg C, 2.) -25 deg C, 0.5 h 2: 75 percent / 90percent aq. formic acid / 0.17 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 61 percent / tetrahydrofuran / 1 h / Ambient temperature 2: 94 percent / 60percent perchloric acid / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

acetic acid-(1-ethynyl-2,2,6-trimethyl-cyclohexyl ester) (87570-48-7) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc oxide; silicon oil / 200 °C / Erhitzen unter vermindertem Druck 2: HCl; water View Scheme

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) + trimethyl orthoformate (149-73-5) → Dimethoxy-2',2' ethyl-2 trimethyl-1,3,3 cyclohexene-1 (86558-53-4)

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 24h; Ambient temperature;	100%

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → C11H19NO

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In methanol; water Reflux;	100%

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → 2,2-dideutero-2-(2,6,6-trimethylcyclohex-1-en-1-yl)ethanal (269057-55-8)

Conditions	Yield
With water-d2; sodium hydride In pyridine at 25℃; for 4h; deuteration;	99.9%

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → (2,6,6-trimethylcyclohex-1-enyl)acetonitrile (57576-15-5)

Conditions	Yield
With hydroxylamine hydrochloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate; N,N-dimethyl-formamide at 100℃;	97%
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / methanol; water / Reflux 2: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / tetrahydrofuran; ethyl acetate / 20 °C / Inert atmosphere View Scheme

pyrrolidine (123-75-1) + (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → 1-<2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl>pyrrolidine (93178-30-4)

Conditions	Yield
In toluene at 60℃; for 1h;	96%
In toluene at 60℃; for 1h;	88%

3-bromo-1-trifluoromethylbenzene (401-78-5) + (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → 1-(3-(trifluoromethyl)phenyl)-2-(2,6,6-trimethylcyclohex-1-enyl)ethanol (1441167-69-6)

Conditions	Yield
Stage #1: 3-bromo-1-trifluoromethylbenzene With iodine; magnesium In tetrahydrofuran for 0.0833333h; Reflux; Stage #2: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde In tetrahydrofuran at -78 - 20℃; for 2h;	90%

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → 2,4,4-trimethyl-3-(2'-hydroxymethyl)-2-cyclohexene (472-65-1)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h;	85%
With lithium aluminium tetrahydride In diethyl ether Heating;
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In diethyl ether
With sodium tetrahydroborate In methanol Inert atmosphere;

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyl-dimethyl-[2-(2,6,6-trimethyl-cyclohex-1-enyl)-vinyloxy]-silane

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran	85%

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) + C13H13NOS2 → (1R,4S,7R,8S,11S)-11-methyl-8-(2′,6′,6′-trimethylcyclohexenemethyl)-4-phenyl-9-oxa-2,10-dithia-5-azatricyclo[5,2,2,01,5]undecan-6-one

Conditions	Yield
With titanium tetrachloride In dichloromethane at -40 - 0℃; for 10h; diastereoselective reaction;	85%

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → (+/-)-dihydroactinidiolide (15356-74-8, 17092-92-1, 19432-05-4, 81800-41-1)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 17h; Heating;	83%
Multi-step reaction with 2 steps 1: 81 percent / m-CPBA (50-60percent), p-TsOH / CHCl3 / 1 h / Ambient temperature 2: 83 percent / silica gel / Heating; Irradiation; microwave irradiation (1.0 kW), 5-10 min View Scheme

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) + S-benzyl malonic acid half thioester (61668-14-2) → S-benzyl (E)-4-(2,6,6-trimethylcyclohex-1-enyl)but-3-enethioate

Conditions	Yield
With 5-methoxy-1H-benzimidazole; ytterbium(III) triflate In tetrahydrofuran at 25℃; for 16h; Doebner-Knoevenagel condensation;	82%

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → (+/-)-aeginetolide (29951-40-4)

Conditions	Yield
With toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid In chloroform for 1h; Ambient temperature;	81%

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) + propionaldehyde (123-38-6) → C14H24O2

Conditions	Yield
With water; sodium hydroxide In N,N-dimethyl-formamide at 30℃; Solvent; Temperature; Reagent/catalyst; Concentration; Aldol Condensation;	81%

3-fluorobromobenzene (1073-06-9) + (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → 1-(3-fluorophenyl)-2-(2,6,6-trimethylcyclohex-1-enyl)ethanol (1441167-61-8)

Conditions	Yield
Stage #1: 3-fluorobromobenzene With iodine; magnesium In tetrahydrofuran for 0.0833333h; Reflux; Stage #2: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde In tetrahydrofuran at -78 - 20℃; for 2h;	75%

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → (+/-)-dihydroactinidiolide (15356-74-8, 17092-92-1, 19432-05-4, 81800-41-1) + (+/-) aeginetolide (19432-07-6, 29951-40-4, 53537-93-2, 70561-84-1, 114247-76-6)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In tetrachloromethane at 0 - 30℃; for 3h; Yields of byproduct given;	A n/a B 73%

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) + phenylbis[(trifluoromethyl)sulfonyl]amine → (E)-2-(2,6,6-trimethylcyclohexen-1-yl)-ethenyl (trifluoromethyl)sulfonate (303779-99-9)

Conditions	Yield
Stage #1: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: phenylbis[(trifluoromethyl)sulfonyl]amine In tetrahydrofuran; hexane at -78℃; Cooling; stereoselective reaction;	73%

1-bromo-3-chlorobenzene (108-37-2) + (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → 1-(3-chlorophenyl)-2-(2,6,6-trimethylcyclohex-1-enyl)ethanol (1441167-65-2)

Conditions	Yield
Stage #1: 1-bromo-3-chlorobenzene With iodine; magnesium In tetrahydrofuran for 0.0833333h; Reflux; Stage #2: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde In tetrahydrofuran at -78 - 20℃; for 2h;	72%

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → 2,4,4-trimethyl-3-(2-oxoethyl)-2-cyclohexen-1-one (186451-82-1) + (3-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-acetaldehyde

Conditions	Yield
With pyridine N-oxide; selenium(IV) oxide In 1,4-dioxane at 80℃; for 4h;	A 15% B 64%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → (E)-2-(2,6,6-trimethylcyclohexen-1-yl)-ethenyl (trifluoromethyl)sulfonate (303779-99-9)

Conditions	Yield
Stage #1: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at 20℃; for 0.5h;	58%

Nonafluorobutanesulfonyl fluoride (375-72-4) + (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → (E)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl nonafluorobutanesulfonate (475673-41-7)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran for 1h; Heating;	52%
With potassium tert-butylate In tetrahydrofuran for 1h; Heating;	52%

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) + 4-fluoro-3-trifluoromethylbenzyl bromide → 2-(4-fluoro-3-(trifluoromethyl)phenyl)-1-(2,6,6-trimethylcyclohex-1-enyl)ethanol (1441167-75-4)

Conditions	Yield
Stage #1: 4-fluoro-3-trifluoromethylbenzyl bromide With magnesium In diethyl ether for 1.25h; Reflux; Stage #2: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde In diethyl ether at -78 - 20℃; for 1h;	42%

4-bromo-2-fluoro-1-(trifluoromethoxy)benzene (105529-58-6) + (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) → 1-(3-fluoro-4-(trifluoromethoxy)phenyl)-2-(2,6,6-trimethylcyclohex-1-enyl)ethanol (1441167-79-8)

Conditions	Yield
Stage #1: 4-bromo-2-fluoro-1-(trifluoromethoxy)benzene With magnesium In diethyl ether for 0.666667h; Reflux; Stage #2: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde In diethyl ether at -78 - 20℃; for 1h;	42%

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2) + 1-bromomethyl-3-methyl-benzene (620-13-3) → 2-m-tolyl-1-(2,6,6-trimethylcyclohex-1-enyl)ethanol (1441167-71-0)

Conditions	Yield
Stage #1: 1-bromomethyl-3-methyl-benzene With magnesium In diethyl ether for 1.33333h; Reflux; Stage #2: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde In diethyl ether at -78 - 20℃; for 1h;	41%

Upstream product

• 79-77-6 (E)-β-ionone 
• 97-97-2 chloroacetaldehyde dimethyl acetal 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 
• 4360-63-8 2-bromomethyl-1,3-dioxolane 
• 7252-83-7 1-bromo-2,2-dimethoxyethane 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 87570-48-7 acetic acid-(1-ethynyl-2,2,6-trimethyl-cyclohexyl ester) 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 128463-60-5 α--2,6,6,-trimethyl-1-cyclohexenemethanol 
• 86558-54-5 2-((E)-2-Methoxy-vinyl)-1,3,3-trimethyl-cyclohexene 
• 14393-45-4 (E)-3-(2,6,6-trimethylcyclohex-1-enyl)acrylic acid 
• 41613-59-6 1-ethynyl-2,2,6-trimethyl-1-cyclohexanol 
• 75-08-1 ethanethiol 

Downstream Products

• 15356-74-8 (+/-)-dihydroactinidiolide 
• 472-65-1 2,4,4-trimethyl-3-(2'-hydroxymethyl)-2-cyclohexene 
• 83646-52-0 3-(2-hydroxyethyl)-2,4,4-trimethyl-2-cyclohexen-1-ol 
• 19432-07-6 (+/-) aeginetolide 
• 269057-55-8 2,2-dideutero-2-(2,6,6-trimethylcyclohex-1-en-1-yl)ethanal 
• 57576-15-5 (2,6,6-trimethylcyclohex-1-enyl)acetonitrile 
• 1441167-83-4 1-(3,4-dichlorophenyl)-2-(2,6,6-trimethylcyclohex-1-enyl)ethanol 
• 1441167-81-2 1-(3-fluoro-4-(trifluoromethyl)phenyl)-2-(2,6,6-trimethylcyclohex-1-enyl)ethanol 
• 1441167-79-8 1-(3-fluoro-4-(trifluoromethoxy)phenyl)-2-(2,6,6-trimethylcyclohex-1-enyl)ethanol 
• 1441167-75-4 2-(4-fluoro-3-(trifluoromethyl)phenyl)-1-(2,6,6-trimethylcyclohex-1-enyl)ethanol 
• 1441167-73-2 2-(3-(trifluoromethyl)phenyl)-1-(2,6,6-trimethylcyclohex-1-enyl)ethanol 
• 1441167-71-0 2-m-tolyl-1-(2,6,6-trimethylcyclohex-1-enyl)ethanol 
• 1441167-69-6 1-(3-(trifluoromethyl)phenyl)-2-(2,6,6-trimethylcyclohex-1-enyl)ethanol 
• 1441167-67-4 1-(3-chlorophenyl)-2-(2,6,6-trimethylcyclohex-1-enyl)ethanone 

Relevant articles and documents

Preparation method of (2, 6, 6-trimethyl-1-cyclohexenyl) acetaldehyde

The invention provides a preparation method of (2, 6, 6-trimethyl-1-cyclohexenyl) acetaldehyde, which comprises the following steps: carrying out Grignard reaction on halogenated acetaldehyde acetal and magnesium powder to prepare a Grignard reagent, carrying out addition reaction on the obtained Grignard reagent and 2, 2, 6-trimethylcyclohexanone, and acidifying and deprotecting the obtained product to obtain (2, 6, 6-trimethyl-1-cyclohexenyl) acetaldehyde. The preparation method provided by the invention has the advantages of cheap and easily available raw materials, low cost, simple steps,safe and environment-friendly operation, easy realization, high reaction atom economy and selectivity, high yield and high purity, and is suitable for green industrial production. The obtained (2, 6,6-trimethyl-1-cyclohexenyl) acetaldehyde can be further used for preparing C14 aldehyde and vitamin A acetate.

Improved Synthesis of 2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde, a Key Intermediate for Drimanerelated Sesquiterpenes

The titel compound is conveniently prepared in 65percent overall yield by a two step synthesis starting from the comercially available β-ionone.

A New General Synthetic Approach to Diterpenes: Application to Syntheses of (+ -)-Taxodione and (+ -)-Royleanone.

High-pressure Diels - Alder reactions of 1,3,3-trimethyl-2-vinyl-1-cyclohexenes 3a,b,i with substituted 1,4-benzoquinones afford, in good yield, highly functionalized tricyclic ring systems which are found in many classes of naturally occuring terpenes.Notably, the reactions of 3a are highly regio- and stereoselective.Efficient, formal syntheses of antitumor diterpenes (+ -)-taxodione and (+ -)-royleanone are reported, which demonstrate the practical application of this new strategy for the preparation of varied terpene systems.Of particular interest is that the high-pressure reactions are accelerated by mild Lewis acids and the regio- and stereoselectivity of these reactions is also improved under the combined high-pressure / Lewis acid conditions in comparison to the high-pressure conditions alone.Indeed, in the reaction of 3a with 2-methoxy-5-methyl-1,4-benzoquinone, ZnBr2 is required to effect the Diels-Alder reaction even at 12 kbar, and endo adduct 12c is formed stereoselectively in 90percent yield.In contrast, low-temperature Ti(IV)-catalyzed reactions of diene 3a with methoxy-substituted 1,4-benzoquinones at atmospheric pressure regioselectively produce dihydrobenzofurans 19 and 20, apparently via alkylation of the quinone Ti(IV) complex by the diene followed by the ring closure.