Bicyclo[3.1.0]hex-2-ene-6-carboxaldehyde

Base Information

• Chemical Name: Bicyclo[3.1.0]hex-2-ene-6-carboxaldehyde
• CAS No.: 7176-16-1
• Molecular Formula: C₇H₈O
• Molecular Weight: 108.14
• Mol file: 7176-16-1.mol

Synonyms:

Chemical Property of Bicyclo[3.1.0]hex-2-ene-6-carboxaldehyde

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Bicyclo[3.1.0]hex-2-ene-6-carboxaldehyde

There total 14 articles about Bicyclo[3.1.0]hex-2-ene-6-carboxaldehyde 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: 72.0%

endo-bicyclo[3.1.0]hex-2-ene-6-carbaldehyde (4729-05-9) → bicyclo[3.1.0]hex-2-en-6-endo-carboxaldehyde (4729-05-9,7176-16-1,34890-01-2,39521-41-0,39521-42-1,39643-60-2,61617-40-1,148152-96-9)

Guidance literature:

With sodium methylate; In methanol; for 24h; Heating;

DOI:10.1021/jo9706133

Reference yield: 55.0%

bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → bicyclo[3.1.0]hex-2-en-6-endo-carboxaldehyde (4729-05-9,7176-16-1,34890-01-2,39521-41-0,39521-42-1,39643-60-2,61617-40-1,148152-96-9)

Guidance literature:

bicyclo[2.2.1]hepta-2,5-diene; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃; for 5h;

With sodium methylate; In methanol; for 24h; Reflux;

Reference yield:

bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → 2-oxabicyclo[3.2.1]octa-3,6-diene (4729-06-0) + bicyclo[3.1.0]hex-2-en-6-endo-carboxaldehyde (4729-05-9,7176-16-1,34890-01-2,39521-41-0,39521-42-1,39643-60-2,61617-40-1,148152-96-9)

Guidance literature:

With peracetic acid; sodium carbonate; In dichloromethane; at 20 ℃; for 2h; Title compound not separated from byproducts;

upstream raw materials:

endo-bicyclo[3.1.0]hex-2-ene-6-carbaldehyde

tetracyclo-[3.2.0.0.^2,7.0^4,6]heptane

(1R,5S,6S,7R)-7-Chloro-bicyclo[3.2.0]hept-2-en-6-ol

bicyclo[2.2.1]hepta-2,5-diene

Downstream raw materials:

1α,5α,6α-bicyclo[3.1.0]hex-2-ene-6-carboxylic acid

N-phenylsulphonyl-exo-6-aminomethylbicyclo<3.1.0>hex-2-ene

Refernces

• 1、 Kim, Won,Kim, Hyangdug,Rhee, Hakjune. "An efficient synthesis of (±)-cis-2-mino-6-hydroxy-9[4'-hydroxyethyl- 2'-cyclopenten-1'-yl]purine". . p. 219 - 224. Retrieved 2007/10/03.
• 2、 Stearns, Ralph A.,Montellano, Paul R. Ortiz de. "Cytochrome P-450 Catalyzed Oxidation of Quadricyclane. Evidence for a Radical Cation Intermediate". . p. 4081 - 4082. Retrieved 2007/10/02.