4221-98-1Relevant articles and documents
High-Throughput Synthesis of (S)-α-Phellandrene through Three-Step Sequential Continuous-Flow Reactions
Miller, Samuel J.,Ishitani, Haruro,Furiya, Yuichi,Kobayashi, Shū
supporting information, p. 192 - 198 (2021/02/05)
The combination of continuous-flow processing with heterogeneous catalysts allows for efficient, sustainable, multistep synthesis. Here, we report the continuous-flow synthesis of a valuable terpene product, phellandrene, from a readily available natural feedstock. The protocol consists of selective hydrogenation using a highly active and stable supported platinum catalyst, dehydrative hydrazone formation, followed by the Shapiro reaction. Appropriate design of the reactor allowed for high productivity and space-time yield. Phellandrene was synthesized on a 30-g scale over 6 h, giving high yields, purity, and productivity.
Novel route to a fruitful mixture of terpene fragrances in particular phellandrene starting from natural feedstock geraniol using weak acidic boron based catalyst
Eisenacher, Matthias,Beschnitt, Stefan,H?lderich, Wolfgang
experimental part, p. 214 - 217 (2012/09/08)
Myrcene, ocimene and in particular phellandrene were selectively generated as products by dehydration of the natural feedstock geraniol over a weak acidic boron pentasil zeolite catalyst in a gas phase reaction. Additionally linalool was formed by rearrangement reaction. The total selectivity of these 4 terpenes is up to 99%.
Triphenylpyrylium tetrafluoroborate-sensitized photochemistry of the terpenes sabinene, α-phellandrene, and α- and γ-terpinene
Climent, Maria-Jose,Miranda, Miguel Angel,Roth, Heinz Dieter
, p. 1563 - 1567 (2007/10/03)
The triphenypyrylium tetrafluoroborate (TPT)-sensitized reactions of several terpene donor molecules, including sabinene (1), α-phellandrene (4), α-terpinene (5) and γ-terpinene (6) give rise to significantly different products than reactions induced by other electron-transfer sensitizers, such as 1,4-dicyanobenzene (DCB). The divergent reactions require decidedly different key intermediates; the products obtained with TPT can be explained by dissociative recombination of the intermediate radical-radical cation pair in the triplet state, generating donor-derived biradicals.
ENANTIOMERIC COMPOSITION OF MONOTERPENE HYDROCARBONS FROM THE LIVERWORT CONOCEPHALUM CONICUM
Valterova, Irena,Unelius, C. Rikard,Vrkoc, Jan,Norin, Torbjoern
, p. 3121 - 3124 (2007/10/02)
Volatiles from the essential oil of the liverwort Conocephalum conicum were analysed.The chirality of the monoterpene hydrocarbons was studied by two-dimensional gas chromatography.All compounds except β-phellandrene showed high optical purity.For the identification of enantiomers, (+)-β-phellandrene and (-)-α-thujene were prepared from (+)-limonene and (+)-sabinene, respectively.Key Word Index: Conocephalum conicum; Hepaticae; liverwort; monoterpene hydrocarbons; (+)-β-phellandrene; (-)-α-thujene; chiral composition
Isotopically Sensitive Branching as a Tool for Evaluating Multiple Product Formation by Monoterpene Cyclases
Wagschal, Kurt,Savage, Thomas J.,Croteau, Rodney
, p. 5933 - 5944 (2007/10/02)
The deuterated substrates geranyl pyrophosphate and geranyl pyrophosphate were employed to examine isotopically sensitive branching in the biosynthesis of monoterpene olefin isomers.By this method, (-)-α-pinene and (-)-β-pinene were shown to be synthesized via a common intermediate by a single cyclization enzyme from grand fir (Abies grandis), as were (-)-α-phellandrene and (-)-β-phellandrene by a single cyclase from lodgepole pine (Pinus contorta).Kinetic isotope effects were determined for the various deprotonations leading to the pinenes and phellandrenes.Key Words: Isotopically sensitive branching, monoterpene biosynthesis, monoterpene cyclase, resin biosynthesis, kinetic isotope effect.
