147133-33-3

Basic information

• Product Name: (cyclopropylidenemethyl)cyclohexane
• Synonyms: (cyclopropylidenemethyl)cyclohexane
• CAS NO: 147133-33-3
• Molecular Weight: 136.237
• Mol File: 147133-33-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (cyclopropylidenemethyl)cyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (cyclopropylidenemethyl)cyclohexane(147133-33-3)
• EPA Substance Registry System: (cyclopropylidenemethyl)cyclohexane(147133-33-3)

Safety Data

• Hazardous Substances Data: 147133-33-3(Hazardous Substances Data)

Upstream product

• 2043-61-0 cyclohexanecarbaldehyde 
• 3607-17-8 3-bromopropyltriphenylphosphonium bromide 

Downstream Products

• 1131452-15-7 C₁₄H₂₂O₄ 
• 1417163-67-7 (Z)-ethyl 6-bromo-7-cyclohexyl-2-methylene-6-heptenoate 
• 1417163-68-8 (E)-ethyl 6-bromo-7-cyclohexyl-2-methylene-6-heptenoate 
• 147133-34-4 2-cyclohexylcyclobutanone 

Relevant articles and documents

Synthesis of Fluorinated Homoallylic Compounds by Fluoroalkyl Radical Mediated Ring Opening of Methylenecyclopropanes

The fluoroalkyl (Rf) radical mediated ring opening of methylenecyclopropanes (MCPs) 1 and subsequent atom transfer were investigated. In the first part, a copper-initiated radical reaction of Rf-X (X = I, Br) with MCP 1 gave homoallylic halides 2 in excellent yields. Similarly, radical reaction of the RfTMS/CsF/PhI(OCOR)2 system with MCP 1 led to homoallylic alcohol esters 3 in moderate to good yields. An efficient synthesis of fluoroalkyl (Rf)-substituted homoallylic halides 2 and homoallylic alcohol esters 3 by fluoroalkyl radical mediated ring opening of methylenecyclopropanes (MCPs) 1 followed by an atom-transfer process is developed.

Iron-Catalyzed Regioselective Alkenylboration of Olefins

The first examples of an iron-catalyzed three-component synthesis of homoallylic boronates from regioselective union of bis(pinacolato)diboron, an alkenyl halide (bromide, chloride or fluoride), and an olefin are disclosed. Products that bear tertiary or quaternary carbon centers could be generated in up to 87 % yield as single regioisomers with complete retention of the olefin stereochemistry. With cyclopropylidene-containing substrates, ring cleavage leading to trisubstituted E-alkenylboronates were selectively obtained. Mechanistic studies revealed reaction attributes that are distinct from previously reported alkene carboboration pathways.