82263-48-7

Basic information

• Product Name: Cyclopropanecarboxaldehyde, 2-phenyl-, (1R,2R)- (9CI)
• Synonyms: Cyclopropanecarboxaldehyde, 2-phenyl-, (1R,2R)- (9CI)
• CAS NO: 82263-48-7
• Molecular Formula: C₁₀H₁₀O
• Molecular Weight: 146.1858
• Product Categories: ALDEHYDE
• Mol File: 82263-48-7.mol
• Article Data: 34

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclopropanecarboxaldehyde, 2-phenyl-, (1R,2R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarboxaldehyde, 2-phenyl-, (1R,2R)- (9CI)(82263-48-7)
• EPA Substance Registry System: Cyclopropanecarboxaldehyde, 2-phenyl-, (1R,2R)- (9CI)(82263-48-7)

Safety Data

• Hazardous Substances Data: 82263-48-7(Hazardous Substances Data)

Upstream product

• 99267-71-7 O,O'-trans-cinnamylidene-L_g-tartaric acid diethyl ester 
• 34271-31-3 trans-2-phenylcyclopropanecarbaldehyde 
• 3471-10-1 (1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid 
• 110659-58-0 (1R,2R)-1-hydroxymethyl-2-phenylcyclopropane 
• 110659-58-0 (1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane 
• 936-98-1 ((S)-2-Phenyl-cyclopropyl)-methanol 
• 1394897-70-1 (1R,1'S,2'S)-1-(2-phenylcyclopropyl)ethane-1,2-diol 
• 1394897-58-5 C₂₀H₂₄O₂S 
• 100-42-5 styrene 
• 82215-37-0 (2R,4R,5S)-3,4-Dimethyl-5-phenyl-2-((E)-styryl)-oxazolidine 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 34271-31-3 trans-2-phenylcyclopropanecarbaldehyde 
• 185135-46-0 ethyl 3E-<(1S,2R)-2-phenyl-1-cyclopropyl>prop-1-enoate 
• 161344-86-1 ethyl 3E-<(1R,2S)-2-phenyl-1-cyclopropyl>prop-1-enoate 
• 22467-91-0 cis-1-(trans-β-Ethoxycarbonylvinyl)-2-phenylcyclopropan 
• 625455-49-4 (1R,1’S,2’S)-1-(2-phenylcyclopropyl)but-3-en-1-ol 
• 625455-48-3 (1S,1’S,2’S)-1-(2-phenylcyclopropyl)but-3-en-1-ol 
• 110659-58-0 (1R,2R)-1-hydroxymethyl-2-phenylcyclopropane 
• 1188287-58-2 C₁₇H₁₄OS 
• 1188287-59-3 C₁₈H₁₆OS 
• 17955-08-7 cis-2-Phenyl-vinyl-cyclopropan 
• 321906-18-7 trans-(2-vinylcyclopropyl)benzene 

Relevant articles and documents

Skeletally Tunable Seven-Membered-Ring Fused Pyrroles

We describe a copper-mediated method that enables the synthesis of seven-membered-ring fused pyrroles (7-mrFPs). The protocol proceeds via an in situ spiro-intermediate ring expansion and tolerates a library of 7-mrFP derivatives with a broad range of functional groups in a simple step with tangible parameters and substrate adaptations. These rare 7-mrFPs are now accessible on a millimolar scale, and selected examples exhibit high antioxidant activity.

Visible-Light Controlled Divergent Catalysis Using a Bench-Stable Cobalt(I) Hydride Complex

While the use of visible light in conjunction with transition metal catalysis offers powerful opportunities to switch between on/-off states of catalytic activity, the next frontier would be the ability to switch the actual function of the catalyst and resulting products. Here we report such an example of multi-dimensional catalysis. Featuring an easily prepared, bench-stable cobalt(I) hydride complex in conjunction with pinacolborane, we can switch the reaction outcome between two widely employed transformations, olefin migration and hydroboration, with visible light as the trigger.

Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases

Ene reductases from the Old Yellow Enzyme (OYE) family reduce the C=C double bond in α,β-unsaturated compounds bearing an electron-withdrawing group, for example, a carbonyl group. This asymmetric reduction has been exploited for biocatalysis. Going beyond its canonical function, we show that members of this enzyme family can also catalyze the formation of C?C bonds. α,β-Unsaturated aldehydes and ketones containing an additional electrophilic group undergo reductive cyclization. Mechanistically, the two-electron-reduced enzyme cofactor FMN delivers a hydride to generate an enolate intermediate, which reacts with the internal electrophile. Single-site replacement of a crucial Tyr residue with a non-protic Phe or Trp favored the cyclization over the natural reduction reaction. The new transformation enabled the enantioselective synthesis of chiral cyclopropanes in up to >99 % ee.