1-(1-cyclohexene)-ethyl-2,4-pentadienoate

Base Information

• Chemical Name: 1-(1-cyclohexene)-ethyl-2,4-pentadienoate
• CAS No.: 97329-95-8
• Molecular Formula: C₁₃H₁₈O₂
• Molecular Weight: 206.285
• Mol file: 97329-95-8.mol

Synonyms:1-(1-cyclohexene)-ethyl-2,4-pentadienoate

Chemical Property of 1-(1-cyclohexene)-ethyl-2,4-pentadienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(1-cyclohexene)-ethyl-2,4-pentadienoate

There total 1 articles about 1-(1-cyclohexene)-ethyl-2,4-pentadienoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(E)-3-(cyclohex-1-en-1-yl)acrylaldehyde (102651-85-4) + ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate (188945-44-0) → (2Z,4E)-ethyl 5-(cyclohex-1-en-1-yl)penta-2,4-dienoate (1423124-54-2) + 1-(1-cyclohexene)-ethyl-2,4-pentadienoate (97329-95-8)

Guidance literature:

ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate; With N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; at -78 ℃; for 0.25h; Inert atmosphere;

(E)-3-(cyclohex-1-en-1-yl)acrylaldehyde; In tetrahydrofuran; methanol; for 10h; Overall yield = 60 %; Inert atmosphere;

DOI:10.1016/j.phytochem.2012.08.001

Reference yield: 64.0%

1-(1-cyclohexene)-ethyl-2,4-pentadienoate (97329-95-8) → 1-(1-cyclohexene)-2,4-pentadien-5-ol (145299-81-6)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; at -70 ℃; for 5h;

DOI:10.1016/0022-2860(92)80123-Y

Reference yield:

1-(1-cyclohexene)-ethyl-2,4-pentadienoate (97329-95-8) → pentademethylretinal (114438-43-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 64 percent / (i-Bu)2AlH / diethyl ether / 5 h / -70 °C

2: 64 percent / MnO₂ / CH₂Cl₂ / 6 h / Ambient temperature

3: 1.) NaH / 1.) THF, 0 deg C, 2.) THF, 0 deg C, 30 min

4: 55 percent / (i-Bu)2AlH / diethyl ether / 5 h / -70 °C

5: 62 percent / MnO₂ / CH₂Cl₂ / 6 h / Ambient temperature

With manganese(IV) oxide; sodium hydride; diisobutylaluminium hydride; In diethyl ether; dichloromethane;

DOI:10.1016/0022-2860(92)80123-Y

upstream raw materials:

(E)-3-(cyclohex-1-en-1-yl)acrylaldehyde

ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate

Downstream raw materials:

1-(1-cyclohexene)-2,4-pentadien-5-ol

pentademethylretinal

1-(1-cyclohexene)-ethyl-2,4,6,8-tetraenoate

(2E,4E)-5-(cyclohex-1-en-1-yl)penta-2,4-dienal

Refernces