109956-89-0

Usage

InChI:InChI=1/C15H20O2/c1-13(2)5-10-4-11(7-16)15(9-17)8-14(15,3)12(10)6-13/h4,7,9-10,12H,5-6,8H2,1-3H3/t10-,12+,14+,15+/m1/s1

Upstream product

• 130543-24-7 (4R,5R)-5-[(E)-2-(4,4-Dimethyl-cyclopent-1-enyl)-vinyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methoxy-methyl-amide 
• 130543-25-8 C₁₈H₂₈O₅ 
• 130543-21-4 (4R,5R)-5-[(E)-2-(4,4-Dimethyl-cyclopent-1-enyl)-vinyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 
• 130559-14-7 C₁₉H₂₆O₃ 
• 130543-20-3 (4,4-Dimethyl-cyclopent-1-enylmethyl)-triphenyl-phosphonium; bromide 
• 130559-16-9 C₂₁H₃₂O₅ 
• 130543-23-6 (4R,5R)-5-[(E)-2-(4,4-Dimethyl-cyclopent-1-enyl)-vinyl]-2,2-dimethyl-[1,3]dioxolane-4-carbonyl chloride 
• 130559-15-8 C₁₉H₃₀O₄ 
• 130543-34-9 Acetic acid (1aS,2S,3S,3aR,6aS,6bS)-1a,2-diformyl-5,5,6b-trimethyl-decahydro-cyclopropa[e]inden-3-yl ester 
• 37841-91-1 (+)-isovelleral 

Downstream Products

• 37841-91-1 (+)-isovelleral 

Relevant academic research and scientific papers

The Mechanism of the Thermal Rearrangement of the Marasmane Sesquiterpene (+)-Isovelleral. Cyclopropane Ring Closure via an Intramolecular Ene Reaction

The reversible thermal conversion of the fungal sesquiterpene isovelleral (2) into (1) is a unique intramolecular ene reaction proceeding via the bicyclic enol (3), which is demonstrated by kinetic studies, deuterium incorporation, and the trapping of (3).

The Thermal Isomerization of the Sesquiterpenes Isovelleral and Merulidial. A Reversible Ring Opening of the cis-Methylcyclopropanecarbaldehyde Group via an Intramolecular Ene Reaction

Fungal sesquiterpene dialdehydes of marasmane and isolactarane types, such as isovelleral (1) and merulidial (7), undergo a reversible thermal rearrangement to produce products (e.g., 2 and 8) with inverted orientations of the cyclopropane rings.The process is shown to involve an intramolecular ene reaction with a bicyclic enol intermediate 13 which was trapped as an E-silyl ether 17.In the presence of D2O, deuterium is incorporated quantitatively into the C-12 methyl groups of 1 and 2.A high kinetic isotope effect is observed for the rearrangement of 1 and its deuterated analogue 24, and the reaction parameters are comparable to those reported for the thermal ring-opening reactions of cis-alkylvinylcyclopropanes and cis-alkyl cyclopropyl ketones.In the presence of weak acid or base, an equilibrium is established between 1, 2, and the hydroazulenic dialdehydes 14 and 15.Dialdehyde 7 reacts less cleanly and incorporates deuterium not only at C-13 but also at C-1 (26).The latter process presumably involves enolization via a sigmatropic hydrogen shift.