124150-82-9

Basic information

• Product Name: Cyclopropanecarboxaldehyde, 3-acetyl-2,2-dimethyl-, (1R-cis)- (9CI)
• Synonyms: Cyclopropanecarboxaldehyde, 3-acetyl-2,2-dimethyl-, (1R-cis)- (9CI)
• CAS NO: 124150-82-9
• Molecular Formula: C8H12O2
• Molecular Weight: 140.17968
• Product Categories: ALDEHYDE
• Mol File: 124150-82-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclopropanecarboxaldehyde, 3-acetyl-2,2-dimethyl-, (1R-cis)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarboxaldehyde, 3-acetyl-2,2-dimethyl-, (1R-cis)- (9CI)(124150-82-9)
• EPA Substance Registry System: Cyclopropanecarboxaldehyde, 3-acetyl-2,2-dimethyl-, (1R-cis)- (9CI)(124150-82-9)

Safety Data

• Hazardous Substances Data: 124150-82-9(Hazardous Substances Data)

Upstream product

• 124062-49-3 (1aS,1bR,4S,5aR)-4-tert-Butyl-1,1,1b-trimethyl-hexahydro-2-oxa-4a-aza-cyclopropa[a]pentalen-5-one 
• 124062-53-9 (3bR,6S)-6-tert-Butyl-3,3,3b-trimethyl-3,3a,3b,5,6,8a-hexahydro-pyrazolo[4',3':3,4]pyrrolo[2,1-b]oxazol-8-one 
• 123-76-2 levulinic acid 
• 124062-48-2 (3S,7aR)-3-tert-Butyl-7a-methyl-2,3-dihydro-7aH-pyrrolo[2,1-b]oxazol-5-one 
• 124062-47-1 (3S,7aR)-3-tert-Butyl-7a-methyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 
• 124062-50-6 (1aS,1bR,4S,5aR)-4-tert-Butyl-1,1,1b-trimethyl-hexahydro-2-oxa-4a-aza-cyclopropa[a]pentalen-5-ol 

Relevant articles and documents

CHIRAL BICYCLIC LACTAMS. AN ASYMMETRIC SYNTHESIS OF CIS-(1S, 3R) DELTAMETHRINIC ACID

Cyclopropanation of a chiral α,β-unsaturated bicyclic lactam derived from tert-leucinol and levulinic acid gave after 4 steps, the title compound in >99percent ee.

Diastereoselective cyclopropanations of chiral bicyclic lactams leading to enantiomerically pure cyclopropanes. Application to the total synthesis of CIS-(1S, 3R)-deltamethrinic acid and R-(-)- dictyopterene C

A novel diastereoselective cyclopropanation based on readily available chiral bicylic lactams (1b-c, 6a-b) has provided a number of enantiomerically pure cyclopropanes. Cyclopropanations of unsaturated lactams (10a-h, 12-14) were performed using sulfur ylides as well as a 3+2 cycloaddition-photolysis sequence and furnished the desired cyclopropane adducts (16, 17, 19, 22) in fair to excellent yields. In all cases involving sulfur ylides, cyclopropanations proceeded with a high degree of exo/endo diastereoselectivity (>;90%). However, the mode of addition, exo vs endo, was found to be highly dependent on the angular substituent of the unsaturated lactam. In the case of diazoalkane cycloadditions, high regioselectivity was observed in all cases although exo/endo selectivity was governed by the diazoalkane employed. Diazoisopropane, being more reactive than diazomethane, normally led to lower diastereomeric ratios. Minor diastereomers could be readily removed by chromatography or in most cases by a single recrystallization to provide diastereomerically pure cyclopropyl bicyclic lactams (16, 17, 19, 22). Applications of this methodology to compounds of biological significance was exemplified by an asymmetric, total synthesis of cis-(1S, 3R)-deltamethrinic acid (34) and R-(-)- dictyopterene C′ (42) in high enantiomeric purity.