Product Name

Synthetic route

(1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol
59057-30-6

(1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol

triphenylphosphine hydrobromide
6399-81-1

triphenylphosphine hydrobromide

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
In methanol for 75h; Ambient temperature;100%
In methanol at 20℃; for 20h;73%
In tetrahydrofuran
3-methyl-5-bromo-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene
38987-92-7

3-methyl-5-bromo-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene

triphenylphosphine
603-35-0

triphenylphosphine

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
In acetonitrile at 50 - 55℃; for 5h; Inert atmosphere;92.8%
In acetonitrile at 50 - 55℃; for 5h; Inert atmosphere;92.1%
(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadien-1-ol
3917-39-3

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadien-1-ol

triphenylphosphine hydrobromide
6399-81-1

triphenylphosphine hydrobromide

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
In methanol for 17h; Ambient temperature;
triphenylphosphine hydrobromide
6399-81-1

triphenylphosphine hydrobromide

Acetic acid (2Z,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienyl ester

Acetic acid (2Z,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienyl ester

A

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

B

β-ionylidenetriphenylphosphonium bromide

β-ionylidenetriphenylphosphonium bromide

Conditions
ConditionsYield
Stage #1: Acetic acid (2Z,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienyl ester With lithium aluminium tetrahydride
Stage #2: triphenylphosphine hydrobromide
(E)-β-ionone
79-77-6

(E)-β-ionone

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

triphenylphosphine hydrobromide
6399-81-1

triphenylphosphine hydrobromide

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Stage #1: (E)-β-ionone; vinyl magnesium bromide
Stage #2: triphenylphosphine hydrobromide Further stages.;
(E)-β-ionone
79-77-6

(E)-β-ionone

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / tetrahydrofuran / 20 h / 20 °C
2: 73 percent / methanol / 20 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 94 percent / tetrahydrofuran / 14 h / Ambient temperature
2: 100 percent / methanol / 75 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran / 24 h / 20 °C
2.1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C
2.2: 24 h / 20 °C
View Scheme
(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate
17974-55-9

(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiAlH4 / diethyl ether / 0.25 h / Ambient temperature
2: methanol / 17 h / Ambient temperature
View Scheme
[5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2-penten-4-ynyl]triphenylphosphonium bromide

[5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2-penten-4-ynyl]triphenylphosphonium bromide

2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol
5244-34-8

2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol

nickel
7440-02-0

nickel

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
In methanol; dichloromethane; ethyl acetate
(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate
17974-55-9

(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate

triphenylphosphine hydrobromide
6399-81-1

triphenylphosphine hydrobromide

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Stage #1: (2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate With lithium aluminium tetrahydride In diethyl ether at 0℃; for 0.5h;
Stage #2: triphenylphosphine hydrobromide In methanol at 20℃; for 24h;
2-(bromomethyl)-1,3,3-trimethylcyclohex-1-ene
59633-88-4

2-(bromomethyl)-1,3,3-trimethylcyclohex-1-ene

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hexane / 4 h / 50 - 55 °C / Inert atmosphere
2.1: potassium hydroxide / isopropyl alcohol / 1 h / -5 - 5 °C / Inert atmosphere
3.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
3.2: 3 h / 20 - 25 °C
4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
C28H32P(1+)*Cl(1-)

C28H32P(1+)*Cl(1-)

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium ethanolate / N,N-dimethyl-formamide / 5 h / -5 - 10 °C / Inert atmosphere
2.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
2.2: 3 h / 20 - 25 °C
3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
diethyl [(2,2,6-trimethylcyclohexyl)methyl]phosphonate

diethyl [(2,2,6-trimethylcyclohexyl)methyl]phosphonate

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium methylate / N,N-dimethyl-formamide / 1 h / 0 - 15 °C / Inert atmosphere
2.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
2.2: 3 h / 20 - 25 °C
3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
triphenyl((2,6,6-trimethylcyclohex-1-enyl)methyl)phosphonium bromide
56013-01-5

triphenyl((2,6,6-trimethylcyclohex-1-enyl)methyl)phosphonium bromide

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hydroxide / isopropyl alcohol / 1 h / -5 - 5 °C / Inert atmosphere
2.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
2.2: 3 h / 20 - 25 °C
3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
3-methyl-5-acetoxy-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene
3917-38-2

3-methyl-5-acetoxy-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
1.2: 3 h / 20 - 25 °C
2.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogen bromide; sodium hydroxide / water; dichloromethane / 2 h / 30 - 35 °C / Inert atmosphere
1.2: 2 h / 35 - 40 °C
2.1: hexane / 4 h / 50 - 55 °C / Inert atmosphere
3.1: potassium hydroxide / isopropyl alcohol / 1 h / -5 - 5 °C / Inert atmosphere
4.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
4.2: 3 h / 20 - 25 °C
5.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: sodium hydroxide; thionyl chloride / 1,2-dichloro-ethane; water / 3 h / 40 - 45 °C
1.2: 5 h / 70 - 75 °C
2.1: acetonitrile / 4 h / 60 - 65 °C / Inert atmosphere
3.1: sodium ethanolate / N,N-dimethyl-formamide / 5 h / -5 - 10 °C / Inert atmosphere
4.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
4.2: 3 h / 20 - 25 °C
5.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: sodium hydroxide; thionyl chloride / 1,2-dichloro-ethane; water / 3 h / 40 - 45 °C
1.2: 5 h / 70 - 75 °C
2.1: 4 h / 105 - 110 °C / Inert atmosphere
3.1: sodium methylate / N,N-dimethyl-formamide / 1 h / 0 - 15 °C / Inert atmosphere
4.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
4.2: 3 h / 20 - 25 °C
5.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
1,3,3-trimethyl-2-chloromethylcyclohexene

1,3,3-trimethyl-2-chloromethylcyclohexene

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: acetonitrile / 4 h / 60 - 65 °C / Inert atmosphere
2.1: sodium ethanolate / N,N-dimethyl-formamide / 5 h / -5 - 10 °C / Inert atmosphere
3.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
3.2: 3 h / 20 - 25 °C
4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: 4 h / 105 - 110 °C / Inert atmosphere
2.1: sodium methylate / N,N-dimethyl-formamide / 1 h / 0 - 15 °C / Inert atmosphere
3.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
3.2: 3 h / 20 - 25 °C
4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
4-bromo-3-methyl-2-buten-1-ol acetate
32659-14-6

4-bromo-3-methyl-2-buten-1-ol acetate

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: acetonitrile / 4 h / 60 - 65 °C / Inert atmosphere
2.1: sodium ethanolate / N,N-dimethyl-formamide / 2 h / 0 - 5 °C / Inert atmosphere
3.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C
3.2: 3 h / 20 - 25 °C
4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: methanol / 4 h / 100 - 105 °C / Inert atmosphere
2.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / -10 - 0 °C / Inert atmosphere
3.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C
3.2: 3 h / 20 - 25 °C
4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: ethanol / 4 h / 105 - 110 °C / Inert atmosphere
2.1: sodium ethanolate / toluene / 2 h / -5 - 5 °C / Inert atmosphere
3.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C
3.2: 3 h / 20 - 25 °C
4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
C25H26O2P(1+)*Br(1-)

C25H26O2P(1+)*Br(1-)

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium ethanolate / N,N-dimethyl-formamide / 2 h / 0 - 5 °C / Inert atmosphere
2.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C
2.2: 3 h / 20 - 25 °C
3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
C25H26O2P(1+)*Cl(1-)

C25H26O2P(1+)*Cl(1-)

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium methylate / N,N-dimethyl-formamide / 2 h / 5 - 10 °C / Inert atmosphere
2.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C
2.2: 3 h / 20 - 25 °C
3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
diethyl 2-methyl-4-acetoxy-2-butenylphosphonate

diethyl 2-methyl-4-acetoxy-2-butenylphosphonate

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium ethanolate / toluene / 2 h / -5 - 5 °C / Inert atmosphere
2.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C
2.2: 3 h / 20 - 25 °C
3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
dimethyl 2-methyl-4-acetoxy-2-butenylphosphonate

dimethyl 2-methyl-4-acetoxy-2-butenylphosphonate

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / -10 - 0 °C / Inert atmosphere
2.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C
2.2: 3 h / 20 - 25 °C
3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
(E)-1-O-acetyl-4-chloro-3-methyl-2-buten-1-ol
24529-80-4

(E)-1-O-acetyl-4-chloro-3-methyl-2-buten-1-ol

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: acetonitrile / 4 h / 70 - 75 °C / Inert atmosphere
2.1: sodium methylate / N,N-dimethyl-formamide / 2 h / 5 - 10 °C / Inert atmosphere
3.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C
3.2: 3 h / 20 - 25 °C
4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
View Scheme
4-palmitoyloxy-2-methyl-2-buten-1-al

4-palmitoyloxy-2-methyl-2-buten-1-al

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
With sodium ethanolate In N,N-dimethyl-formamide at -5 - 5℃; for 3h; Wittig Olefination; Inert atmosphere;91.3%
(E)-4-acetoxy-2-methylcrotonaldehyde
26586-02-7

(E)-4-acetoxy-2-methylcrotonaldehyde

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
With sodium ethanolate In N,N-dimethyl-formamide at -5 - 0℃; for 2h; Solvent; Temperature; Reagent/catalyst; Wittig Olefination; Inert atmosphere;91%
With sodium ethanolate In N,N-dimethyl-formamide at -5 - 5℃; for 2h; Time; Inert atmosphere;90.7%
(Z)-3-methyl-4-oxobut-2-enoic acid
70143-04-3

(Z)-3-methyl-4-oxobut-2-enoic acid

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

13-cis-retinoic acid
4759-48-2

13-cis-retinoic acid

Conditions
ConditionsYield
Stage #1: (Z)-3-methyl-4-oxobut-2-enoic acid; 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide With sodium hydroxide In isopropyl alcohol at 20 - 30℃; for 3h; Wittig Olefination; Inert atmosphere;
Stage #2: With hydrogenchloride; palladium diacetate In isopropyl alcohol at 60℃; pH=7 - 8;
86.3%
Stage #1: (Z)-3-methyl-4-oxobut-2-enoic acid; 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide With sodium hydroxide In isopropyl alcohol at 20 - 30℃; for 3h; Wittig Olefination; Inert atmosphere;
Stage #2: With hydrogenchloride; palladium diacetate In isopropyl alcohol at 60℃; pH=7-8; Inert atmosphere;
86.3%
5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

4-formyl-2-[3-oxo-2-methyl-(1E)-propenyl]pyridine
188554-16-7

4-formyl-2-[3-oxo-2-methyl-(1E)-propenyl]pyridine

2-[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]pyridine
188554-17-8

2-[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]pyridine

Conditions
ConditionsYield
With sodium ethanolate In ethanol76%
5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

(Z)-3-Iodo-4-oxo-but-2-enoic acid ethyl ester
174836-86-3

(Z)-3-Iodo-4-oxo-but-2-enoic acid ethyl ester

(2Z,4E,6E,8E)-3-Iodo-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid ethyl ester
743421-41-2

(2Z,4E,6E,8E)-3-Iodo-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (Z)-3-Iodo-4-oxo-but-2-enoic acid ethyl ester With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide
Stage #2: 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide Further stages.;
74%
5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

bis(3-formyl-3-methyl-2-propenyl) sulfide
251291-80-2

bis(3-formyl-3-methyl-2-propenyl) sulfide

retinyl sulfide
268728-47-8

retinyl sulfide

Conditions
ConditionsYield
Stage #1: 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide; bis(3-formyl-3-methyl-2-propenyl) sulfide In DMF (N,N-dimethyl-formamide) at -20℃;
Stage #2: With sodium methylate In DMF (N,N-dimethyl-formamide) at -20 - 20℃; for 3.5h;
68%
4-t-butyldimethylsilyloxy-2-butynal
75859-97-1

4-t-butyldimethylsilyloxy-2-butynal

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

tert-Butyl-dimethyl-[(4Z,6E,8E)-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trien-2-ynyloxy]-silane
75867-37-7

tert-Butyl-dimethyl-[(4Z,6E,8E)-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trien-2-ynyloxy]-silane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran for 3h; Ambient temperature;52%
5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

2-methyl-3-[3-(1-methyl-2-oxoethylidene)-cyclohex-1-enyl]-propenal
454442-05-8

2-methyl-3-[3-(1-methyl-2-oxoethylidene)-cyclohex-1-enyl]-propenal

C43H60

C43H60

Conditions
ConditionsYield
With sodium methylate In methanol for 1h;40%
5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

13-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethylcyclohex-1-enyl]-2,7,11-trimethyltrideca-2,4,6,8,10,12-hexaenal

13-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethylcyclohex-1-enyl]-2,7,11-trimethyltrideca-2,4,6,8,10,12-hexaenal

A

(all-E)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene
135589-15-0

(all-E)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene

B

(9'Z)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene

(9'Z)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene

Conditions
ConditionsYield
Stage #1: 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide; 13-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethylcyclohex-1-enyl]-2,7,11-trimethyltrideca-2,4,6,8,10,12-hexaenal With sodium methylate In methanol; dichloromethane at 20℃; for 3h; Wittig condensation;
Stage #2: With Dowex 50W-X8 (H+) In methanol; dichloromethane at 20℃; for 0.333333h;
A 28%
B 10%
(2E,4E,6E,8E,10E,12E,14E)-2,7,11,15,19-pentamethylicosa-2,4,6,8,10,12,14,18-octaenal
103956-99-6, 1071-52-9

(2E,4E,6E,8E,10E,12E,14E)-2,7,11,15,19-pentamethylicosa-2,4,6,8,10,12,14,18-octaenal

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

trans-gamma-Carotene
472-93-5

trans-gamma-Carotene

Conditions
ConditionsYield
With sodium methylate In methanol; N,N-dimethyl-formamide
2-Methyl-4-(thioacetyl)-2-(E)-butenal
72053-20-4

2-Methyl-4-(thioacetyl)-2-(E)-butenal

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

11-cis-Retinylthioacetat
72053-19-1, 72075-18-4

11-cis-Retinylthioacetat

Conditions
ConditionsYield
(i) nBuLi, (ii) /BRN= 2075468/; Multistep reaction;
2-Methyl-4-(thioacetyl)-2-(E)-butenal
72053-20-4

2-Methyl-4-(thioacetyl)-2-(E)-butenal

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

11-trans-Retinylthioacetat
72053-19-1, 72075-18-4

11-trans-Retinylthioacetat

Conditions
ConditionsYield
(i) nBuLi, (ii) /BRN= 2075468/; Multistep reaction;
acetic acid trans-4-oxo-but-2-enyl ester
38982-39-7

acetic acid trans-4-oxo-but-2-enyl ester

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

Acetic acid (2E,4E,6E,8E)-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyl ester

Acetic acid (2E,4E,6E,8E)-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyl ester

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane 1.) 1 h, -60 deg C; 2.) 2 h to RT; Yield given;
5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

ethyl trans-13,14-dihydro-13-desmethyl-13,14-methyleneretinoate
89887-40-1

ethyl trans-13,14-dihydro-13-desmethyl-13,14-methyleneretinoate

ethyl cis-13,14-dihydro-13-desmethyl-13,14-methyleneretinoate
89827-99-6

ethyl cis-13,14-dihydro-13-desmethyl-13,14-methyleneretinoate

Conditions
ConditionsYield
With potassium tert-butylate benzene, 1) 15 min 2) 8h, r.t.; Yield given. Multistep reaction. Yields of byproduct given;
1-Carbethoxy-2-formyl-2-methyl-cyclopropan
20417-63-4

1-Carbethoxy-2-formyl-2-methyl-cyclopropan

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

ethyl trans-13,14-dihydro-13,14-methyleneretinoate
89887-37-6

ethyl trans-13,14-dihydro-13,14-methyleneretinoate

ethyl cis-13,14-dihydro-13,14-methyleneretinoate
89827-98-5

ethyl cis-13,14-dihydro-13,14-methyleneretinoate

Conditions
ConditionsYield
With potassium tert-butylate benzene, 1) 15 min 2) 22h, r.t.; Yield given. Multistep reaction. Yields of byproduct given;
4,4-dimethoxy-3-methyl-but-2-en-1-al
62285-97-6

4,4-dimethoxy-3-methyl-but-2-en-1-al

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

2-((1E,3E,5E,7E)-9,9-Dimethoxy-3,8-dimethyl-nona-1,3,5,7-tetraenyl)-1,3,3-trimethyl-cyclohexene

2-((1E,3E,5E,7E)-9,9-Dimethoxy-3,8-dimethyl-nona-1,3,5,7-tetraenyl)-1,3,3-trimethyl-cyclohexene

Conditions
ConditionsYield
With sodium ethanolate In ethanol; dichloromethane at 0℃; for 1h;
5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

4-(tert-butyldimethylsilyloxy)-2-methylbutanal
115797-15-4

4-(tert-butyldimethylsilyloxy)-2-methylbutanal

13,14-dihydro-all-trans retinol
115797-14-3

13,14-dihydro-all-trans retinol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride 1.) Wittig-reaction; Multistep reaction;
5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienylidenetriphenylphosphorane
71987-74-1

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienylidenetriphenylphosphorane

Conditions
ConditionsYield
With phenyllithium In diethyl ether for 0.0833333h; Ambient temperature;
5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

(2E,4E,6E,8E,10E)-2,7,11-trimethyl-12-oxotrideca-2,4,6,8,10-pentaenal
160456-53-1

(2E,4E,6E,8E,10E)-2,7,11-trimethyl-12-oxotrideca-2,4,6,8,10-pentaenal

(all-E)-sintaxanthin
4586-97-4

(all-E)-sintaxanthin

Conditions
ConditionsYield
With sodium hydride In dichloromethane at 20℃; for 48h; Yield given;
(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial
5056-17-7

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

12'-apo-β-caroten-12'-al
1638-05-7

12'-apo-β-caroten-12'-al

Conditions
ConditionsYield
With sodium hydride In dichloromethane at 20℃; for 64h; Yield given;
With sodium methylate In methanol at 0℃; for 0.5h; Wittig olefination;
5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

4-formyl-2-[3-oxo-2-methyl-(1E)-propenyl]pyridine
188554-16-7

4-formyl-2-[3-oxo-2-methyl-(1E)-propenyl]pyridine

A

2-[(1E,3Z,5E,7E)-2,4-Dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-1,3,5,7-tetraenyl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hexa-1,3,5-trienyl]-pyridine

2-[(1E,3Z,5E,7E)-2,4-Dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-1,3,5,7-tetraenyl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hexa-1,3,5-trienyl]-pyridine

B

2-[(1E,3Z,5E,7E)-2,6-Dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-1,3,5,7-tetraenyl]-4-[(1Z,3E,5E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hexa-1,3,5-trienyl]-pyridine

2-[(1E,3Z,5E,7E)-2,6-Dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-1,3,5,7-tetraenyl]-4-[(1Z,3E,5E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hexa-1,3,5-trienyl]-pyridine

C

2-[(1E,3E,5E,7E)-2,6-Dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-1,3,5,7-tetraenyl]-4-[(1Z,3E,5E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hexa-1,3,5-trienyl]-pyridine

2-[(1E,3E,5E,7E)-2,6-Dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-1,3,5,7-tetraenyl]-4-[(1Z,3E,5E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hexa-1,3,5-trienyl]-pyridine

D

2-[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]pyridine
188554-17-8

2-[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]pyridine

Conditions
ConditionsYield
With sodium ethanolate 1.) EtOH, room temp., 2.) CH3NO2, reflux; Yield given. Multistep reaction;
5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

(2E)-4-[(tert-butyldiphenylsilyl)oxy]-2-fluorobut-2-enal
186953-22-0

(2E)-4-[(tert-butyldiphenylsilyl)oxy]-2-fluorobut-2-enal

(7E,9E,13E)-tert-butyldiphenylsilyl 13-demethyl-13-fluororetinyl ether
186953-39-9

(7E,9E,13E)-tert-butyldiphenylsilyl 13-demethyl-13-fluororetinyl ether

Conditions
ConditionsYield
With n-butyllithium 1.) THF, hexane, -78 deg C, 2.) THF, hexane, 25 deg C, 5 h; Yield given. Multistep reaction;
5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

(Z)-1-(tert-butyldimethylsilyloxy)-3-iodo-3-methylprop-2-ene
148802-00-0

(Z)-1-(tert-butyldimethylsilyloxy)-3-iodo-3-methylprop-2-ene

A

tert-butyldimethylsilyl Δ13-(Z)-retinyl ether
118304-54-4

tert-butyldimethylsilyl Δ13-(Z)-retinyl ether

B

tert-Butyl-[(2Z,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyloxy]-dimethyl-silane
118304-54-4, 118353-70-1

tert-Butyl-[(2Z,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyloxy]-dimethyl-silane

Conditions
ConditionsYield
With potassium tert-butylate; tert.-butyl lithium In diethyl ether; pentane at -75 - 25℃; for 6h; Wittig reaction;
4,4'-diapo-ψ,ψ-carotene-4,4'-dial
13920-19-9, 5056-18-8

4,4'-diapo-ψ,ψ-carotene-4,4'-dial

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

3,7,11,15,20,24,28,32-octamethyl-1,34-bis(2,6,6-trimethylcyclohex-1-enyl)tetratriaconta-1,3,5,7,9,11,13,15,17,19,21,23,25,27,29,31,33-heptadecaene
24513-48-2

3,7,11,15,20,24,28,32-octamethyl-1,34-bis(2,6,6-trimethylcyclohex-1-enyl)tetratriaconta-1,3,5,7,9,11,13,15,17,19,21,23,25,27,29,31,33-heptadecaene

Conditions
ConditionsYield
With sodium hydride In dichloromethane Wittig reaction;67 % Spectr.
6,6'-diapocarotene-6,6'-dial
34561-05-2

6,6'-diapocarotene-6,6'-dial

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

3,9,13,18,22,28-hexamethyl-1,30-bis(2,6,6-trimethylcyclohex-1-enyl)triaconta-1,3,5,7,9,11,13,15,17,19,21,23,25,27,29-pentadecaene

3,9,13,18,22,28-hexamethyl-1,30-bis(2,6,6-trimethylcyclohex-1-enyl)triaconta-1,3,5,7,9,11,13,15,17,19,21,23,25,27,29-pentadecaene

Conditions
ConditionsYield
With sodium hydride In dichloromethane Wittig reaction;66 % Spectr.

[(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadien-1-yl](triphenyl)phosphonium bromide Specification

[(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadien-1-yl](triphenyl)phosphonium bromide, with the CAS registry number 62285-98-7, is also named as Phosphonium, [(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadien-1-yl]triphenyl-, bromide (1:1). This chemical's molecular formula is C33H38BrP and molecular weight is 545.53. What's more, its systematic name is [(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadien-1-yl](triphenyl)phosphonium bromide.

You can still convert the following datas into molecular structure:
(1)SMILES: [Br-].C(/C1=C(/CCCC1(C)C)C)=C\C(=C\C[P+](c2ccccc2)(c3ccccc3)c4ccccc4)C
(2)Std. InChI: InChI=1S/C33H38P.BrH/c1-27(22-23-32-28(2)15-14-25-33(32,3)4)24-26-34(29-16-8-5-9-17-29,30-18-10-6-11-19-30)31-20-12-7-13-21-31;/h5-13,16-24H,14-15,25-26H2,1-4H3;1H/q+1;/p-1/b23-22+,27-24+;
(3)Std. InChIKey: WZGAXXYWWOUQHF-IUKQBHTCSA-M 

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