1486517-24-1

Basic information

• Product Name: 1-(5-cyclopropyl-3,4-dihydronaphthalen-1-yl)cyclobutanol
• CAS NO: 1486517-24-1
• Molecular Weight: 240.345
• Mol File: 1486517-24-1.mol

Chemical Properties

• CAS DataBase Reference: 1-(5-cyclopropyl-3,4-dihydronaphthalen-1-yl)cyclobutanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(5-cyclopropyl-3,4-dihydronaphthalen-1-yl)cyclobutanol(1486517-24-1)
• EPA Substance Registry System: 1-(5-cyclopropyl-3,4-dihydronaphthalen-1-yl)cyclobutanol(1486517-24-1)

Safety Data

• Hazardous Substances Data: 1486517-24-1(Hazardous Substances Data)

Upstream product

• 144464-63-1 5-oxo-5,6,7,8-tetrahydronaphthalen-1-yl trifluoromethanesulfonate 
• 28315-93-7 5-Hydroxy-1-tetralone 
• 1486517-51-4 5-cyclopropyl-3,4-dihydronaphthalen-1(2H)-one 
• 1191-95-3 cyclobutanone 
• 1486518-50-6 4-bromo-8-cyclopropyl-1,2-dihydronaphthalene 
• 33892-75-0 5-Methoxy-1-tetralone 

Relevant articles and documents

Enantioselective halogenative semi-pinacol rearrangement: Extension of substrate scope and mechanistic investigations

The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodology will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behaviour studies.

Enantioselective organocatalytic fluorination-induced Wagner-Meerwein rearrangement

Cracked under strain: Strained allylic cyclobutanols and cyclopropanols readily undergo a ring expansion described by the title rearrangement. This reaction is promoted by catalytic amounts of 1 and displays high tolerance with respect to the substrate scope. The corresponding β-fluoro spiroketone products are isolated in high yields and with excellent stereoselectivities. EDG=electron-donating group, EWG=electron-withdrawing group. Copyright

Enantioselective organocatalytic iodination-initiated Wagner-Meerwein rearrangement

The present manuscript describes a high-yielding enantioselective semipinacol transposition, initiated by an electrophilic iodination event. The title transformation makes use of the anionic phase-transfer catalysis (PTC) paradigm for chirality induction. Thus, when combined appropriately, the insoluble cationic iodinating reagent S9 and the lipophilic phosphoric acid L9 act as an efficient source of chiral iodine that performs the semipinacol transposition of strained allylic alcohols A x to β-iodo spiroketones Bx in good yields and with high levels of diastereo- and enantio-induction. The product β-iodo spiroketones could be derivatized stereospecifically and without stereoerosion, giving rise to products inaccessible directly from a semipinacol rearrangement.