Ethanone, 1-(1S,2R,4S)-bicyclo[2.2.1]hept-5-en-2-yl-(9CI)

Base Information

• Chemical Name: Ethanone, 1-(1S,2R,4S)-bicyclo[2.2.1]hept-5-en-2-yl-(9CI)
• CAS No.: 159651-24-8
• Molecular Formula: C9H12O
• Molecular Weight: 136.194
• DSSTox Substance ID: DTXSID70362526
• Nikkaji Number: J655.440G
• Wikidata: Q82145685
• Mol file: 159651-24-8.mol

Synonyms:159651-24-8;Ethanone, 1-(1S,2R,4S)-bicyclo[2.2.1]hept-5-en-2-yl- (9CI);1-[(1S,2R,4S)-2-bicyclo[2.2.1]hept-5-enyl]ethanone;1-[(1S,4S,5R)-5-bicyclo[2.2.1]hept-2-enyl]ethanone;DTXSID70362526;(1S,4S)-5alpha-Acetylnorborn-2-ene

Chemical Property of Ethanone, 1-(1S,2R,4S)-bicyclo[2.2.1]hept-5-en-2-yl-(9CI)

Chemical Property:

• PSA: 17.07000
• LogP: 1.78760
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 136.088815002
• Heavy Atom Count: 10
• Complexity: 193

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CC2CC1C=C2
• Isomeric SMILES: CC(=O)[C@@H]1C[C@@H]2C[C@H]1C=C2

Technology Process of Ethanone, 1-(1S,2R,4S)-bicyclo[2.2.1]hept-5-en-2-yl-(9CI)

There total 2 articles about Ethanone, 1-(1S,2R,4S)-bicyclo[2.2.1]hept-5-en-2-yl-(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:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + methyl vinyl ketone (78-94-4,25038-87-3) → 2-acetyl-5-norbornene (5063-03-6) + C9H12O (159651-24-8) + (2S)-1-bicyclo[2.2.1]hept-5-en-2-yl-ethanone (159699-92-0)

Guidance literature:

With [Ru(η5-C8H7)((S,S)-BIPHOP-F)(acetone)][SbF6]; lithium diisopropyl amide; In dichloromethane; at -20 ℃; for 48h; Overall yield = 76 %; Overall yield = 68.4 mg; Molecular sieve; Schlenk technique; Inert atmosphere;

DOI:10.1002/hlca.201600139

Reference yield:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + methyl vinyl ketone (78-94-4,25038-87-3) → C9H12O (159651-24-8) + bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (824-60-2,824-61-3,5063-03-6,65166-67-8,107740-92-1,128441-68-9,58001-95-9)

Guidance literature:

methyl vinyl ketone; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

cyclopenta-1,3-diene; In dichloromethane; optical yield given as %ee; Inert atmosphere; Molecular sieve;

DOI:10.1021/om300346s

Reference yield: 43.0%

C9H12O (159651-24-8) + 2-nitro-benzaldehyde (552-89-6) → (E)-1-((1S,2R,4S)-bicyclo[2.2.1]hept-5-en-2-yl)-3-(2-nitrophenyl)prop-2-en-1-one

Guidance literature:

With potassium carbonate; sodium hydroxide; In neat (no solvent); at 20 ℃; for 0.166667h; Schlenk technique;

DOI:10.1021/acs.orglett.0c04162

upstream raw materials:

cyclopenta-1,3-diene

methyl vinyl ketone

Downstream raw materials:

biperiden hydrochloride

C₁₅H₂₃NO

biperiden

Refernces

• 1、 Thamapipol, Sirinporn,Ludwig, Bettina,Besnard, Céline,Saudan, Christophe,Kündig, E. Peter. "Ruthenium Lewis Acid-Catalyzed Asymmetric Diels–Alder Reactions: Reverse-Face Selectivity for α,β-Unsaturated Aldehydes and Ketones". . p. 774 - 789. Retrieved 2016/10/17.