Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-(1-methylethyl)-, (1S,2S,3S,4R)- (9CI)

Base Information

• Chemical Name: Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-(1-methylethyl)-, (1S,2S,3S,4R)- (9CI)
• CAS No.: 278173-27-6
• Molecular Formula: C₁₁H₁₆O
• Molecular Weight: 164.247
• Mol file: 278173-27-6.mol

Synonyms:Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-(1-methylethyl)-, (1S,2S,3S,4R)- (9CI)

Chemical Property of Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-(1-methylethyl)-, (1S,2S,3S,4R)- (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-(1-methylethyl)-, (1S,2S,3S,4R)- (9CI)

There total 15 articles about Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-(1-methylethyl)-, (1S,2S,3S,4R)- (9CI) 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: 82.0%

(4S,5S)-2-((1R,2S,3S,4S)-3-Isopropyl-bicyclo[2.2.1]hept-5-en-2-yl)-4,5-diphenyl-[1,3]dioxolane (271578-32-6) → (1R,2S,3S,4S)-3-Isopropyl-bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde (271578-25-7,271578-36-0,278173-27-6)

Guidance literature:

With acetic acid; at 80 ℃;

DOI:10.1016/S0040-4039(00)00039-3

Reference yield: 80.0%

(1R,2S,3S,4S,5S,6S)-5-Bromo-6-((1S,2S)-2-hydroxy-1,2-diphenyl-ethoxy)-3-isopropyl-bicyclo[2.2.1]heptane-2-carbaldehyde → 3-isopropylbicyclo[2.2.1]hept-5-ene-2-carboxaldehyde (271578-25-7,271578-36-0,278173-27-6)

Guidance literature:

With zinc trifluoromethanesulfonate; 2,4-dichlorophenoxyacetic acid dimethylamine; zinc; at 80 - 90 ℃;

DOI:10.1016/S0040-4039(00)00039-3

Reference yield:

(E)-4-methylpent-2-enal (24502-08-7) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → 3-isopropylbicyclo[2.2.1]hept-5-ene-2-carboxaldehyde (271578-25-7,271578-36-0,278173-27-6) + (1R,2S,3S,4S)-3-Isopropyl-bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde (271578-25-7,271578-36-0,278173-27-6) + (1R,2R,3R,4S)-3-isopropylbicyclo[2. 2. 1]hept-5-ene-2-carboxaldehyde (271578-25-7,271578-36-0,278173-27-6) + (1S,2S,3S,4R)-3-isopropylbicyclo[2. 2. 1]hept-5-ene-2-carboxaldehyde (271578-25-7,271578-36-0,278173-27-6)

Guidance literature:

With trifluorormethanesulfonic acid; In water; at 22 ℃; Title compound not separated from byproducts;

DOI:10.1021/ol051476w

upstream raw materials:

(E)-4-methylpent-2-enal

cyclopenta-1,3-diene

(1S,2R,3R,4R)-3-Isopropyl-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde

(4S,5S)-2-((1R,2S,3S,4S)-3-Isopropyl-bicyclo[2.2.1]hept-5-en-2-yl)-4,5-diphenyl-[1,3]dioxolane