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

Base Information

• Chemical Name: (1R,2S,4R)-2-methylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde
• CAS No.: 72204-08-1
• Molecular Formula: C₉H₁₂O
• Molecular Weight: 136.194
• DSSTox Substance ID: DTXSID10447109
• Nikkaji Number: J726.969B
• Wikidata: Q82265904
• Mol file: 72204-08-1.mol

Synonyms:72204-08-1;(1R,2S,4R)-2-methylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde;SCHEMBL8836120;DTXSID10447109;(1beta,4beta)-5-Methylnorborna-2-ene-5beta-carbaldehyde

Chemical Property of (1R,2S,4R)-2-methylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 136.088815002
• Heavy Atom Count: 10
• Complexity: 195

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CC2CC1C=C2)C=O
• Isomeric SMILES: C[C@@]1(C[C@H]2C[C@@H]1C=C2)C=O

Technology Process of (1R,2S,4R)-2-methylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde

There total 2 articles about (1R,2S,4R)-2-methylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde 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:

2-methylpropenal (78-85-3,25120-30-3) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + acrolein (107-02-8,25068-14-8) → (+/-)-endo-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (19926-90-0) + exo-2-methylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde (34618-30-9,34618-31-0,40441-67-6,72203-36-2,72204-08-1,112710-18-6,116299-25-3,126924-44-5,142506-91-0) + endo-bicyclo[2.2.1]hept-5-ene-2-methyl-2-carboxaldehyde (34618-30-9,34618-31-0,40441-67-6,72203-36-2,72204-08-1,112710-18-6,116299-25-3,126924-44-5,142506-91-0) + exo-2-formylbicyclo[2.2.1]hept-5-ene (5453-80-5,19926-88-6,19926-90-0,58001-94-8,69831-12-5,69831-13-6,72203-35-1,96443-40-2,96443-41-3)

Guidance literature:

With tris(pentafluorophenyl)borate; In dichloromethane; at -78 ℃; for 2h; optical yield given as %de; diastereoselective reaction; Molecular sieve;

DOI:10.1002/anie.201106497

Reference yield:

2-methylpropenal (78-85-3,25120-30-3) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + acrolein (107-02-8,25068-14-8) → (+/-)-endo-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (19926-90-0) + exo-2-methylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde (34618-30-9,34618-31-0,40441-67-6,72203-36-2,72204-08-1,112710-18-6,116299-25-3,126924-44-5,142506-91-0) + endo-bicyclo[2.2.1]hept-5-ene-2-methyl-2-carboxaldehyde (34618-30-9,34618-31-0,40441-67-6,72203-36-2,72204-08-1,112710-18-6,116299-25-3,126924-44-5,142506-91-0) + exo-2-formylbicyclo[2.2.1]hept-5-ene (5453-80-5,19926-88-6,19926-90-0,58001-94-8,69831-12-5,69831-13-6,72203-35-1,96443-40-2,96443-41-3)

Guidance literature:

With tris(pentafluorophenyl)borate; In dichloromethane; at -78 ℃; for 2h; optical yield given as %de; diastereoselective reaction; Molecular sieve;

DOI:10.1002/anie.201106497

Reference yield:

endo-bicyclo[2.2.1]hept-5-ene-2-methyl-2-carboxaldehyde (34618-30-9,34618-31-0,40441-67-6,72203-36-2,72204-08-1,112710-18-6,116299-25-3,126924-44-5,142506-91-0) → exo (anti 1,2 syn-2,3 methyl-2 phenyl-3 propanediol-1,3 yl-1)-5 endo methyl-5 bicyclo<2.2.1>heptene-2 (119031-19-5,119069-87-3,119069-88-4,119069-89-5)

Guidance literature:

Multi-step reaction with 5 steps

1: diethyl ether; CH₂Cl₂ / 15 h / Ambient temperature

2: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH₂Cl₂, -50 deg C, 20 min, 2.) -50 deg C, 5 min,

5: lithium aluminium hydride / diethyl ether / 3 h / -78 °C

With lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4020(01)81704-X

upstream raw materials:

2-methylpropenal

cyclopenta-1,3-diene

acrolein

Downstream raw materials:

exo(syn 2,3 syn 3,4 dimethyl-2,4 phenyl-4 trimethylsiloxy-3 butanone-1 yl-1)-2 endo methyl-2 bicyclo<2.2.1>heptene-5

exo-(syn-2,3 dimethyltertiobutylsiloxy-3 methyl-2 phenyl-3 propanone-1 yl-1)-5 endo methyl-5 bicyclo<2.2.1>heptene-2

exo (anti 1,2 syn-2,3 methyl-2 phenyl-3 propanediol-1,3 yl-1)-5 endo methyl-5 bicyclo<2.2.1>heptene-2

exo(syn 2,3 hydroxy-3 methyl-2 phenyl-3 propanone-1 yl-1)-5 endo methyl-5 bicyclo<2.2.1>heptene-2